Relationships

What’s Your Most Awkward Date Story?

Awkward Date

One day, several years ago, I got a text from a guy named Rob…

“Want to get a drink?” it said, then suggested a fancy bar in a trendy neighborhood.

An image of Rob floated into my mind: dark hair, short stature. I had recently met him at a friend’s barbecue, where he talked about his affinity for aquatic animals and vintage children’s books. I was surprised yet happy to hear from him, and we made a date for the following week.

The day of the date arrived. I walked up to the bar, smoothing my hair in that excited-yet-anxious way reserved exclusively for those moments leading up to dates and interviews. I scanned the bar. I saw no Rob.

Then, somebody waved.

I squinted. It was a slightly familiar looking stranger — very tall and very blond. How did I know that guy? I scanned my brain, where I discovered the answer: IT WAS A DIFFERENT ROB. This Rob was a work acquaintance I had begrudgingly shared my number with and never expected to see again. But now he thought we were on a date. Because, technically, we were.

“Hi!” I said, hoping my face resembled the face of a person who was meeting someone on purpose.

And then, I sat through a looooooooong drink with a person I did NOT mean to go on a date with. Rob was a bit of an aggrandizer. He shared stories of his recent trip (“A rugby match in England!”) and photos of his new apartment (“The view is killer! The kitchen is huge!”), while I offered up what I hoped was a convincing smile. After far too much of this, the accidental date was over.

Forever after, I was careful to put last names — or at the very least descriptions — into my phone. (Cut to months later, when my contacts list contained entries like “Dog Park Mike” and “Silly Hat Evan.”) But the Accidental Date will live on in infamy.

To that end, I’d love to hear about your awkward dating experiences. What’s your best/worst awkward date story?

P.S. Great dating advice and the ultimate first date uniform.

  1. B says...

    Couldn’t wait to get home and read the comments’ section on this :). While I’ve certainly had a number of cringe worthy dates, my favorite story to tell is a guy that I met on an app. His profile was normal enough, and we went rock climbing. The date was pretty quotidian until he took me to dinner. At McDonald’s. Because he wanted to sample their dipping sauces. At McDonald’s, he proceeded to rant about how he had recently been laid off and how his former boss just had it out for him. Spoiler alert – he was still unemployed and was now living with his mother. The man was 27 years old. Despite all of this, he proceeded to ask me on a second date. I did not go on another.

  2. a says...

    One summer when I was home from college, I ran into a guy I’d grown up with and we struck up an interesting conversation about politics and current events. When he asked if I wanted to meet up for coffee that weekend to continue the dialogue, I agreed – somewhat naively, I guess I thought we were meeting up as friends, but it was soon clear that he thought of it as a date. Slightly awkward, since I didn’t feel like there was any attraction there, but he was being nice and non-creepy, so I thought – hey, afternoon coffee is pretty low-stakes, I’ll give it a little chance. UNTIL…. when we stepped out of the coffee spot onto the (wide, parking-lined, 20 MPH speed limit) street, he PHYSICALLY moved me to the inside of the walkway and said, somewhat forcefully and VERY seriously, “I don’t want anyone to think I’m pimping you out.” I laughed uncomfortably, and he emphasized – “No, I’m serious. You need to stay on this side of me.” Needless to say, we did NOT spend any more time together that summer!

  3. Chantsy says...

    So this isn’t my story but my sisters. When we were 18 (we’re twins) a guy we worked with awkwardly asked out my sister. I’ll admit, having yet to jump into the dating pool, I was a little envious. The night of the date she left the house and I envisioned all the fun she was about to have-how lucky! Little did I know that upon his arrival at our home she saw another girl sitting in the back seat of his car. She assumed it must be a friend even though the whole thing felt really odd. Fast forward past a round of mini golf and drinks and she quickly finds out that this girl is his girlfriend! What his intentions were to this day, we have no idea, but what a creep.

    Also, the first guy I dated often asked if my sister wanted to come with us when we hung out together. That definitely rubbed me the wrong way.

  4. L says...

    I can’t stop laughing, this has truly made my day.glad to know some people have had worse experiences than me

  5. Karin says...

    Guy was 2 hours late picking me up for dinner date. Finally shows and asks if we can just go to coffee instead because he’s too tired for the restaurant. During coffee he tells me about a boil on his back that he’s having lanced the next day and asks if I want to see it.

    • M says...

      OMG!

    • Emily says...

      LOL, I can’t imagine!!!

    • naomi says...

      Did you take a picture? OMG

  6. Kate the Great says...

    Acey was cute and cool. He was my college dormmates’ friend– they all, the three funny females and Acey, were from the same small town.

    I don’t remember how he asked me or who else we went with, but it was a group date with a bunch of strangers. No big; this is what college experiences are all about, right? Meh, not so much– the activity was spelunking, and if you get in trouble and you need to ask for help, what happens if you only know one person’s first name?

    Nevertheless, appropriate hiking attire, all out into one vehicle, drive out to the middle of a forest to a huge hole in the ground where we met another stranger, who was our guide. He hands out helmets, makes sure none of us are claustrophobic, basic ground rules, here we go. I’m excited; this sounds fun, and I’ve always wanted to do this.

    The first hole is fun. We all end out the other side of the hole successfully and raring for more. The guide says, “Well, I know of another spelunking place behind a waterfall that could be fun. Are you all game?” We are, but when we arrive, there is no waterfall. The water is still frozen where the waterfall source would flow. But we go anyway.

    I quickly discover that this is not crawling on hands and knees over dry and dark rocks through tight spaces, like the last one. This is hiking, legs spread apart, on two thin ledges coated by water with cold water between. If you slip, you get wet. Your heavy hiking boots become heavier and your pants stick to your legs so they can’t bend the way they should. And then, my legs began to tremble from the cold and the exertion. Uncontrollably and violently. Acey, a cute but complete stranger, tried to hold my hand, but it’s hard to do this hike single-file while holding anyone’s hand, wet or not.

    I survived, but he never spoke to me again. I love hiking and have tried all sorts of outdoorsy activities with joy, but this was not a successful date.

    • Ellie says...

      This comment made my entire week and I can’t even explain to myself why xxoo

    • Kate the Great says...

      I forgot some details– on our way back from the wet, cold, and uncontrollable trembling, I was trying to take my boots and socks off and roll my pants up. While in the back seat of a car. With my date sitting right next to me and someone else on the other side. I was all elbows and accidentally phwapping people in the face and flinging water everywhere. Yep, pretty awkward.

      I did see Acey on campus later, but he either didn’t hear me or.intentionally ignored me.

  7. Rachael says...

    Oh! And to clarify—the next weekend I went out with the guy I had originally thought I was saying yes to, and it was even weirder! First Jack took me to a movie (and then I made up an excuse for why I had to go home) and then the second Jack the next weekend asked me to homecoming—he showed up with a “thank you pumpkin” (presumably bc he was thanking me for going out with him?) and we went to the dance, then we went back to his apartment and started watching Unbroken and he just randomly started licking the palm of my hand. IT WAS SO WEIRD.

    After that I did not date guys named Jack…

  8. Valeria says...

    I am the one who have been an awkward date once. When I was in my early 20, a friend arranged me a blind date with this smart – she said – and handsome work collegue of her so in a beautiful summer night I wore a pretty dress, took my bike, rode all through the town and met him in a bar. Yes, he was smart and handsome indeed and talking was going very well, but in half an hour I started feeling sick, a cramping pain I could not ignore and I easily recognized: damned irregular period. Smiling I took my bag and told him I was going to the toilet just for a minute. Just around the corner, maybe with the help of the air conditioning, I felt very sick and I had to run to the bathroom, where I found that the ladies’ was, obviously, taken. (Warning: the following text may contain strong images.) Don’t ask me to describe how dirty the men bathroom was after a few hours of service for dozens drinking men. I would never sit on a toilet like that. But I did. I felt so so so so bad. I couldn’t actually stand and I felt I was about to collapse, but I still needed the toilet so I couldn’t leave the horrible place. I have a vague memory that I texted to the guy that I was in the bathroom feeling a little sick, “sorry, but don’t worry for me”. And then I called a bunch of girlfriends whom I know were together in that moment and asked them to come with some analgesic and drive me home, because I wasn’t able to ride my bike back. I think I stayed in that bathroom for almost an hour. Twenty years later I’m still trying to forget that I tried to lie on the floor (don’t scream, I’ve warned you), while every now and then people knocked on the door. My date perhaps? I don’t know. No voice called for me so maybe, if he came, once he saw that I was not in the ladies bathroom, he assumed I was somewhere else, maybe outside. I don’t really actually know what came to his mind, poor guy, but he was still in the bar when I finally emerged, susteined by three girls, shivering and looking like Courtney Love in her worst moments. I didn’t dare explain anything to him, neither then nor after, prefering to live as mysterious or jerk or drug addict in his memory. Everyone deserves an awkward date story to tell and laugh at, even him.

    • Jennifer says...

      I was the awkward date. At a concert (second date, I think, & definitely last) I accidentally dropped my entire purse into a porta potty. Phone, wallet, keys, all of it. I won’t elaborate on the details but it was not my most shining moment. Fair accident, could have happened to anyone, but it was me & it was awful.

  9. Rachael says...

    I have TOTALLY done that! Accepted the date, he showed up, and it was not the Jack I had in mind. To make things worse, he ended up working with my husband years later, he saw a picture on my husband’s desk and told my husband he’d dated me, and my husband said flat-out “there’s no way she would have dated you.” Then I was constantly running into him for the next couple of years…soooooo awkward.

  10. Mimi says...

    I’m very short and look quite young. When I was 26, I went on a date with a guy I was really into. As we were being seated at the restaurant, the waiter gave me the kids’s menu and a bunch of crayons…

    • Jessica says...

      Oh man! 😂 this one tops it off! I’m dying of laughter!

    • MM says...

      I’m dying!!!!!!

    • TJP says...

      This is GOLD.

    • Alyssa says...

      This might be the winner.

    • Vanessa says...

      Did you color?

  11. Christine says...

    My worst date was my own doing.

    We met at his apartment that was blocks away from breweries and bars, and started the walk over to our first brewery. As we were crossing the street, I tripped over my own feet (in sneakers!) and FACE PLANTED into the pavement. Passerby’s gasped and my date burst out in nervous laughter.
    In a hurry to nurse my embarrassment, I over drank that evening and my date offered to let me crash on his couch. When I woke up the next morning, there he was, curled up/smushed into his dog’s bed on the floor next to the couch. He proceeded to do a full re-enactment of my loud snoring and teeth grinding and then asked if we could make out.
    I politely declined, apologized and got out of there.

  12. Leigh says...

    I have had my fair share of awkward dates (I’m the common denominator here, I realize), but two stand out the most in my mind. One was mine, one was not.

    I met this guy at summer camp – as counselors – and, as Bravo has taught us when you stick a bunch of twentysomethings in close proximity for long periods of time, flirting happens. It was the end of the summer, and the end of our responsibility of watching after children, so we threw a party. Fueled by encouraging friends and some adult beverages, we set a date for the following week. In the harsh light of day, I realized my mistake; beyond our matching counselor shirts and sandal tan lines, we had absolutely nothing in common, but it was too late.

    We met at a nearby bar for drinks before heading to a movie. During drinks, we were interrupted by a guy I had been casually dating and his friend for some seriously awkward small talk. In the residual shudder of that discomfort, we excused ourselves and walked down the street to the movie theater. He proceeded to stare at me for the ENTIRE MOVIE. If you ever have that feeling of someone watching you, try picturing that feeling when the eyes watching you are twelve inches from yours. He continued to text me throughout the school year but I tried to do my best polite ghosting and never went on a second date. On graduation day, I was crossing the street and waving to my friend, only to realize someone in front of her was waving back. Guess who.

    The second awkward date that stands out was my roommate’s. She had met this guy on a dating app that turned out to not be what she was expecting. She then brought him back to our apartment because she knew I was home and was hoping to make me the unwitting “third wheel,” and he would get the hint and leave. He did not. He sat on our futon and told me how well the date was going and how much he liked her, while she literally left us to hide out in the other room. I don’t remember how long it took for him to finally go home, but it was approximately three episodes of The Office later.

  13. Alex says...

    In college, on a first date with a friend of a friend. I didn’t finish my pizza at dinner and offered my leftovers to him since I was going out of town the next day and didn’t want them to go bad. He accepted. As he was walking me back to my apartment, we passed a homeless man. He asked my date, “Hey man, do you think you could spare some pizza? I’m starving.” My date’s response? “No, sorry, I need it.” Yeah…. no second date.

  14. Eleanor says...

    I tell my friends I’m on bumble for great stories, not for love, ha! I grew up in a very conservative fundamentalist religion, which discouraged dating and any opposite-sex relationships outside of marriage. Crazy! It’s been a STEEP learning curve when it comes to dating… which means that some red flags I don’t notice until they are in the rearview mirror.

    One bumble first date told me more than he probably anticipated when it came up that he had recently gotten out of a long-term relationship with a much older man.

    Another bumble first date, after rescheduling our coffee date twice, didn’t offer to pay for my drink and after 45 minutes of rambling about how great his life had been when he lived in Europe, ended the date by saying “Well I’m gonna bounce.”

    Another guy (who I didn’t even bother meeting), told me that all women are like porta-potties… occupied or full of sh*t.

    Then there’s the guy I gently rejected after one date, but he started showing up at my church, unannounced and uninvited. Giving off seriously creepy vibes. I told him that his being there was making me uncomfortable, but he kept coming. Took almost two months to convince church leadership that he wasn’t on a spiritual journey. They told him he was welcome if he was looking for God, but not if he was looking for me. Thankfully, he listened to them and I haven’t seen him since.

  15. Sarah says...

    When I was 19 I dated a guy who’s family did not approve of me, regardless of the fact that they had attended the same church as my family for years and I’d been friends with their daughter since we were in kindergarten. I’d grown tired and increasingly frustrated with this and cut to his university department booze cruise!! After a couple of drinks I found myself chatting with one of his professors for perhaps a little too long. The prof gave me his number and I took it half out of fear of upsetting his teacher and mayyyyyybeee spite. Cut to two weeks later and I’d broken up with my puppy love boyfriend when they offered him a big birthday party I couldn’t attend and I find the prof’s number in my purse. If the first mistake was going out on a date with my exes professor who was 10 years older than me, the second was blurting out on the phone that the day of our date happened to be my birthday. Ugh. Instead of a quiet cafe meal, the prof surprised me by taking me to that big time restaurant that every city has (it revolved) and boring me to tears with alternating tales of the girlfriend he’d broken up with who was 10 years his senior (about my age now) and his area of study: soil liquifaction. Then I really messed up. Instead of insisting he drive me home, I gave into his pleas to go back to his place because he had a gift for me. I was pretty sure he was harmless but I got anxious when he slipped out of the room at his house and came back WITH A RIBBON AND BOW TIED AROUND HIS BODY! (It is at this point I always must pause to point out he was still fully clothed). The card read “For your birthday I give you the gift of myself. Handle with care!” I almost choked on my embarrassment. I extricated myself from there after a polite kiss and never saw him again. Apparently he gave my ex a failing grade on the next paper he turned in.

    • Tori says...

      Oh NO! Bold move, prof.

    • lee says...

      I laughed out loud at the ribbon. I can’t imagine! It’s cringe worthy, but I’d watch a whole movie about it.

  16. a says...

    Several years ago I went on a first date with this guy, let’s call him Brad. First date was fine -not great but he was cute and nice enough and polite. Well, I mentioned on the date that a group of our friends were going on a camping/kayaking trip at a nearby river campground for a few days that weekend. Brad asked if he could come too. It was a big group of people so I figured why not, the more the merrier! He asked to carpool with my best friend and me, and we agreed. A few days later we pick him up and he only has a small bag with him, weird for a camping trip but he had insisted that he was a veteran camper, so OK. This man not only did not bring a tent or hammock or ANYTHING to sleep in the whole weekend, he didn’t even bring any food other than a half empty box of Cracker Jacks. He spent the weekend sleeping in and stinking up my car (I was not about to share my sleeping bag with him as he had assumed) and eating all of my food (he even got mad at me when we didn’t make and pack a meal for him on one of our hikes). Even worse, he spent the whole trip whining about how much he hated camping/kayaking/the outdoors/everything under the sun, peppered with inappropriate sexual advances. Needless to say I never spoke to him again after dropping him off after that terrible trip.

  17. Alexa says...

    Many years ago, I was a bike commuter in DC, zipping down 16th street daily to work. Most days, I saw an attractive guy in a suit standing on the same street corner. How odd to see him daily, I thought, but figured he must be waiting for a bus at the same time I was on my way to work. One day I worked up the nerve to approach him and, after a brief chat, asked if he wanted to meet up. (What was wrong with me??) We met at a sushi restaurant that ended up to be wildly expensive. He said “I’m glad I ate before coming because I could never afford to eat a full meal with these prices”…and there I was, starving. As we talked, I found out he was standing on that street corner passing out literature for the Church of Scientology. He invited me to go to the Founding Church of Scientology building, and since the date was such a disaster, I agreed, based on my sheer curiosity of what it could be about. He toured me through the public information area and told me all sorts of information about L. Ron Hubbard and about advancing through the levels of Scientology. He also suggested I try this thing called an E-meter supposedly for measuring one’s spiritual state. At that point, I kinda panicked and wondered how to get out of there, fast! As the mother of two girls now, I hope they develop a bit more common sense than I had at that point.

    • A says...

      As a former DC resident i can totally picture this and it gives me such joy hahaha

  18. Jenna says...

    This is the best comments section ever.

    I once went on a date with a guy, that was going well enough. We went for drinks and then decided to go to another place for supper. On the drive, he pulled over to an ATM so that he could MAKE HIS CHILD SUPPORT PAYMENTS! He couldn’t do that at literally any . other. time?

    • A Martin says...

      This made me laugh out loud! OMG!

    • Jessica says...

      Ha ha!!!! NO!

    • KC says...

      That is quite possibly the least subtle, yet least verbal, way of telling someone that you have non-resident kids that I have ever heard of.

  19. Elle says...

    My best friend was seeing this guy she was really into, and they decided to set me up with his roommate. The goal was for us to hit it off so well that we could eventually all go on countless double dates together.

    He picks a really nice hotel bar and I meet him there shortly after work. I knew I was not attracted to him right off the bat, but he seemed nice and I was curious to get to know him better…BIG MISTAKE.

    Thirty minutes into the date this guy asks me if I showered every night or morning??? Then proceeded to ask me if I would like to take a shower with him after the date so we could explore each other’s bodys. After asking the question he did this creepy eyebrow raise and began staring at my legs.

    Needless to say I aborted that situation real fast. I also never let me friend set me up after that!

  20. Emily says...

    These reader comments are giving me life right now!

  21. Megn says...

    I sat at the bar with a glass of wine, waiting for the man who was meeting me for dinner. He arrived, we were seated at a table, he ordered for both of us, no consultation.

    The waiter arrived with sake the man had ordered. I went to sip the last 1/2 of my wine. The man reached across the table and removed it from my hand, gave the glass to the waiter, and then poured me a sake.

    DESPITE THIS level of controlling behavior, I developed a raging crush on him that lasted the better part of a year. I apologize to myself in retrospect.

  22. Marla says...

    Once, on a blind date, the guys said to me “You have a bigger vocabulary than most of the girls I’ve gone out with.” I used the word “marketable”. Obviously not a plus because he never called me again.

  23. alison says...

    Oof. I went on a date with a dude who voted for The Current President.

    In his tinder profile, it didn’t mention anything political, seemed harmless, looked like a normal hipster. My profile was very honest – I was wearing a Phish tshirt, I’m an artist, I work at an art museum, women’s march pink hat pic, etc etc, hippy hippy hippy.

    We’re chatting a cool enough bar, I ask him about what he does, what he listens to on his very long commute – he says audio books and podcasts, and *really* bad music – I was willing to let that go for now. He was a little boring in general, and not very funny, but chalked it up to nerves.

    We keep chatting about why I moved to where we live — to which I say “well, with the world on fire, I decided I didn’t want to keep working for big pharma and needed a city/job that more aligned with my morals,” and then I paused and asked “wait, are you liberal?”

    To which he sheepishly said “Nah…”
    I ask “…did you vote for…” and he says “Yah…”

    I take the final swig of my drink because I’m ready to hit the bricks – but HE ORDERS ANOTHER ONE FOR HIMSELF, so, I say “Okay, let’s chat. Tell me, would you vote for him again? [yes, he says] Tell me everything! WHY?!”

    I figured, what did I have to lose except to learn about a perspective I NEVER get in my life (for good reason! ha!) Turns out this was the first election he voted in, mind you, we are both in our 30s. He talked about how taxation is theft, how he doesn’t believe in public schools, and how he thought this conversation “wouldn’t come up tonight.” OK YEAH ON WHAT PLANET. I asked him WHY would he want to go out with me?! Like he thought a bleeding heart lib would want to date an Alex Jones listening Libertarian conspiracy theorist.

    We continued to talk politics, in a very civil way, it honestly was eye opening, and he walked me to my car – after asking if that was too chauvinist. He tells me that he wants to see me again! And I tell him that I just don’t see this working out. The end. *curtain* *bows*

    • Tasha says...

      What eye opening thing did you learn about him wanting you to die?

    • Mari says...

      OMG haha
      My best friend wrote on her tinder profile that she’s against our current president (Brazil, but it could totally be the US). She says it’s to avoid this sort of thing and that sometimes some guy will match her only to curse her. “at least he’s not asking me out” HAHA

    • alison says...

      @tasha – oh, just that there are young-ish folks that seem like they could be sane / on our side, that somehow grew up in a similar manner, yet our courses/morals etc strayed SOOOO far from each other.

      @mari – yes, I’m luckily no longer dealing w/ dating apps but saw SO many folks w “swipe left/right if you voted for ____” It should be mandatory to avoid things like this! haha!

  24. Adriana says...

    I used to work on Capitol Hill for a Congressman. One year, we were moving offices and an IT guy came in to set up our system. He was pretty cute and we did some serious flirting. I saw him later that day on the Metro and was thrilled when he asked me out for lunch the next day. We decided to meet at the cafeteria at my building. The next day, when I arrived at the cafeteria, we exchanged pleasantries, and I suggested we get in line for some food. He told me to go ahead, because he had brought his lunch. So I went and ordered, paid for my food, and joined him at a table. He then pulled out a peanut butter sandwich and a small bag of chips from his backpack. He dumped the the bag of chips into his sandwich and proceeded to eat. The whole lunch was so awkward, I don’t even remember what we talked about. I also found out he was only 19, a good 5 years younger than I. Later that night, I could only laugh about the whole experience!

    • Hilary says...

      I lived in France for 2.5 years. I tried French dating apps while I was there. During the first course (so maybe 15 minutes into our meal) a guy I was on a first date with made a reference to the “international government that runs everything.” I asked him what he was talking about. He then went into a ten minute explanation of the Illuminati and it’s structure. According to this guy the Brits and Dutch are in the ones in charge. I definitely did not go on a second date with this guy.

    • Em says...

      I need to know when this was because I worked on the Hill for a long time and I never had a cute IT man come into my office!

  25. Joanna B says...

    I met a guy on OKCupid, which I’m not even sure anyone uses anymore, and he asked me out to dinner. Before we had even met, he would send excessively long (but interesting) missives over the chat function, asking me questions and wanting to get to know me. So I thought it had the potential to be a good date. At dinner, he mentioned offhandedly that he was starting a business that would help people create better dating profiles. Basically you could pay for men or women (whomever you were interested in dating) to review and offer feedback about how appealing/interesting your profile was. He then proceeded to tell me that he had checked out my Instagram, and he believed that I had more attractive photos there than the ones I had posted to my dating profile. It was sort of a backhanded compliment, and I wasn’t sure how to respond. Dinner ended uneventfully, and I went home not sure what to think of it all. Cut to a couple of weeks later when I’m on another date (with the man who would be my husband, yay!) and I see him out with a woman who was clearly his wife. Turns out he had just been testing out his business venture by creating his own dating profile and trying to figure out if he make it really good. Basically, I was an unwitting guinea pig, and he was a liar.

    • Gemma says...

      NOooooooo 😮. This is horrible but hilariously tacky 😂

  26. Lara says...

    About three years ago I matched with a guy on Tinder who was visiting my home country. Not being able to meet straight away (he was moving around, did not have wi-fi at times, etc), we kept chatting even after he returned back at his country. It was fun and we seemed to get along really well. So after a few months, when he would come back to Europe, he stopped by again and we finally met and spent a few days together, travelling around for our “first date”. During those days he would frequently make various sarcastic comments about my teeth (which were not perfectly straight back then), my feet (he found my foot to be huge. they are 39/8.5, the most popular size) as well as other stuff, such as my social freakiness (granted, I am a shy introvert). Back then I was very inexperienced and had super low self esteem, so I did not say much to his mean remarks. Despite everything, the long conversations had also already made me fall in love and I truly liked him, both online and in real life. Long story short, he left me soon afterwards and we have never spoken or met again. Today, with the pink glasses long gone, I feel thankful for this horrible experience and everything else I have learned since. It happened shortly before the #metoo movement, so even if I was abused “only” mentally, I feel like I have “risen” together with all the other women. Today I have found myself, believe in my power, beauty and right to be as I am. And needless to say, would not even sit through a date with a man like him again, ever.
    I believe my experience falls on the dark, not funny spectrum here in this section. Yet I thought I would share it anyways, with the hope that, if someone young and inexperienced as me back then reads this, they would find their inner strength sooner.

    • Denise says...

      It took me 50+ years to get where you are, so bravo! Thanks for sharing <3

  27. Katey says...

    This is fun! I used to rock climb and one evening I was climbing with some friends and I must have been exuding something because two suitors appeared. One, whose name I don’t recall so I’ll call him “John,” was the first to approach me. We set a date. On this date we went to a restaurant with the word “egg” featured in the title. It has since shuttered. The food was mediocre, but the conversation was stunning. As in, I was stunned. He played the didgeridoo, he told me. Once he played it in the bathtub and the sound vibrations made him see beautiful colors, he told me. He talked a lot about rock climbing. The rocks speak to him, he told me, as he held his hand up in the air as though he were gripping the sheer face of a rock.

    It was utterly bizarre and I was super nice the entire time, as if I’m really into didgeridoo magic, but when he dropped me off at my apartment I told him I was in love with someone else…. because I didn’t know how to say “no thanks” to another date OR fend off an unwanted kiss! And perhaps part of me knew I was soon to be in love with that OTHER guy who wanted to ask me out at the rock gym. He’s normal and we’re married and all is right with our little world.

    • tina crisas says...

      Hahahaha, so funny!!! I lol’ed at “didgeridoo magic”.

    • Sara says...

      Katey this is so so funny, and what an ending!

  28. Eva says...

    In college, a guy I had just met asked me out for Valentine’s Day. I said sure, he was pretty cute and there were worse ways to spend Valentine’s. He had me meet him at his apartment where he showed me *several* dances he had choreographed to Craig David songs, asked out-of-nowhere if he could name my boobs, and showed off his extensive collection of Tommy Hilfiger polo shirts. When I mentioned after a couple of hours that I was hungry, he took me to a Taco Bell drive-thru and dropped me back off at my dorm. Aahhh, college.

    • Faith says...

      Dying at “showed off his extensive collection of Tommy Hilfiger polo shirts”!

    • rachel says...

      pretty sure that was Tom Haverford from Parks and Rec….

  29. MK says...

    Met a man off Tinder who seemed like the male version of me – worked nearly the same job for a competitor company and had a hilarious sense of humor. When I showed up at the restaurant, I was immediately not attracted to him (small hands). His first subject of discussion: how much he loves open relationships, watching men dominate women with anal sex, etc. etc. all while we ate pasta. He then asked me to show him on his phone’s map where I live so that we could have an “exploratory sex session.” I politely declined. When the bill came, he didn’t offer to pay, so I paid my half. Then he took a picture of the bill with his phone and informed me that he was going to expense it to work since we worked in the same field, thus making money off our date. I told him I was not romantically interested, but then he attempted to forcibly kiss me outside the restaurant and put his hands down the back of my pants. Sent a number of follow-up texts that I ignored.

    Fast forward two years, I am leaving that job for another. They asked me to help train my replacement and I agreed before they told me who it was. Yep, this same cheap, small-handed sexual aggressor. When he showed up for the orientation he seemed not to know who I was. Then over a work lunch he asked me if we could have an exploratory sex session. To this day, I do not know if he truly had no recollection of me or if he fully remembered and was just hopeful that persistence would win! He continues to occasionally reach out to me with invitations to hang out.

    • Kate says...

      Eww, awkward!

    • Shannon Murphy says...

      “Exploratory sex session” 😂😭😂😭

    • Jessica says...

      This man should not be allowed to get away with his behaviour! Can you call him out on his behaviour?

  30. Hannah says...

    This story is not mine – overheard a conversation between two women on a bus.
    “He kept asking me to go out with him, over and over and over. Finally, I gave in and said yes. He was such a nice guy, you know…. So we’re sitting in his car, he leans over and kisses me, then we start making out, and then my water broke.”

    • Sarah says...

      So this is silly but when I was very pregnant with my third child (would go into labour days later) I hauled my tired self off to a ramen date with my husband. A cool place with a line up to get seats at a communal table. We decided somehow spontaneously to pretend the whole time we were there that we were on a first date. We found it hilarious. He said one thing about me not looking the same as my profile pic but otherwise just pretended I wasn’t massively pregnant. The young girls seated next to us definitely gave us some funny looks. Still makes me laugh to this day.

    • rindi says...

      OH MY! This one is the winner. Best awkward date story ever!

  31. Kathi says...

    I went to coffee with a gentleman in my town who I met on a Dating website. All he did was talk about the Bible, and quote Bible verses abd ask me to join his Bible Blog, for an hour. Never asked me one question about me. Don’t get me wrong I am spiritual and religious but that was over the top. I excused myself politely thanked him for coffee and left. That was Wednesday. Another gentleman I had been chatting with who was from Wisconsin just moved to AZ to take care if his parents. Said he just joined a new church in the neighboring town and asked if I would like to meet him for Sunday Services. Said its a safe place. I said sure. As I drove to the Church a thought came to me. There are about 25 churches in this town what would the odds be if the guy from Wednesday belonged to this Church too? I shook my head. No, impossible. I walked up into the vestble and the pastor said you look new. I introduced myself said I was meeting a fellow parishioner named Cal. The pastor then belted out Cal she is gere Kathi is here. The whole congegation turned to look at my beet red face. And Lo and Behold standing right next to Cal was Joe the guy I had coffee with on Wednesday. Awkward!!!!! He walks forward and says what are you doing here. I embarrassingly said well I church hop on weekends to find the best fit for me. Red as a Beet as Cal said you two know each other. I said yes nervously we are acquaintances, made awkward introductions. Then service started Cal and I took a seat and Joe took one 2 pews behind and the whole time I felt eye piercing daggers on my back. And then even more embarrassing Cal started too much PDA putting his arm around me, trying to hold my hand. Needless to say I said Thank you God for getting me thru that Awkward hysterical situation. Of course all my friends roared with laughter. Ha Ha
    It was pretty funny and ironic.

    • Sarah says...

      Omg I’m choking on my cracker. Hahahahahahaha

  32. Emily says...

    I met a guy online, but we had mutual friends and he lived around the corner. Out of character, I let him drive to our second date. When he arrived, I smelled a whiff of booze, but plenty of people have a pre-date drink to take the edge off so I wasn’t concerned. We put his name in for a table at a popular restaurant, who texts when your table is ready, and went to a brewery next door to wait. We chatted over beers. He finished his and went to the bar. Came back with two beers (one for me? nice!) then drank them both (wow). Told him I was surprised the restaurant hadn’t texted yet and he said “oh I left my phone in the car.” What? We walked over to the restaurant, found our table was ready… and I realized he was very drunk. He was an embarrassment during dinner, waving and calling too loudly for the waitress, took his glasses off to eat, and made a mess. He insisted on paying, but I had to add to his bad tip. I took his keys and drove us home. Halfway through the 3 mile drive, he started loudly claiming he was sober to drive home and I should stop the car, which I didn’t. I offered to drive him all the way home but he refused, so I dropped myself off. He asked if he could come in, definitely not. (He texted an apology the next day but I did not see him again.)

  33. Meg says...

    Old Spaghetti Factory.
    Long table = far away and trying hard to hear each other.
    Super chewy bread in a basket.
    Dude butters his bread.
    His hand jerks as his bite releases on that chewy bread.
    Butter blob rocket flies off the bread, flings over the long table (in slow-mo) and sticks to my cheek.
    First horror.
    Then we couldn’t stop laughing.
    Then awkwardness.

    Butter blob rocket to the face… will never forget that one hahah.

    • sarah says...

      amazing storytelling here. laughed so hard.

  34. Tori says...

    Not exactly a date but shortly after graduating from film school a friend and I were working on a project together. We had to meet up to go over some work and he asked me to come to a barbers…I go, thinking I must be mistaken about something, but no. I stand there, while he gets his haircut. Also we were both freelancers so it’s not like his schedule was packed. I found my way out of that project soon after.

  35. Mags says...

    I didn’t really date in high school but when I was a senior I really wanted to go to prom (and this was before I would have the confidence to go alone). No one was asking me so after much deliberation I decided to ask a junior guy I knew from an after school club. I wasn’t attracted to him or close to him but we had mutual friends who were going to prom together and I thought it would be fun to go as a group.

    I finally got the courage to ask him out and he told me he would think about it and let me know — which took a while, long enough that by the time he told me “no” it felt I couldn’t ask anyone else. Worse yet, he must have thought I was really interested in him because to make me feel better he offered to take me to dinner and after we could watch everyone else be announced at the prom. I don’t remember agreeing to this, but I must have because the night of prom, when I wanted to be dancing with my friends, I was out on the worst date of my life. Neither of us were attracted to each other, neither of us wanted to be there, and yet both of us were so polite. Soon after I graduated and we have not kept in touch. Except that the following year, when he was senior, he took my sister to prom and apparently they had a great time!

  36. Akiko says...

    lol something similar happened to my college roommate and two Dan K.’s! She was interested in one Dan K. but kept texting the other updates of her whereabouts, like “I’m heading to a house party now!” Each time, he’d respond, “Okay…” She had been texting our quirky neighbor, who she was NOT into. But since this was college, they ended up at the same party and making out anyway. Apparently, he was a good kisser.

  37. Anna says...

    Once I went on a date with a person I was casually dating and he invited a friend who was visiting from out of town.. he told me to bring a friend of my own to meet up with them for drinks. He didn’t tell me his friend was a straight woman who he clearly was about to hook up with. SO. Awkward.

  38. Oma says...

    This isn’t really a story, per se, but once I was at dinner with my family and while waiting for our table, the host looked me in the eye and said: you should come here more often.

    It was was weird because A) my family (parents and four siblings) were with me and B) this was CRACKER BARREL.

    • Kristin says...

      Ahhhhh, Cracker Barrel!! Haha

  39. SJ says...

    I’m recently divorced, and have found the concept of dating again to be more painful that the betrayal and attorney fees. However, at the coaxing of my friends and sister, I agreed to a date with “Stephen”.
    Over dinner, I mentioned my love for the beach, to which he responded that he has a fear of the water. It turns out, he isn’t afraid of the ocean, but of ALL water. Including showers and baths. After this revelation, he began to perform magic tricks, citing that he thought I would “like to watch him play with his balls”. Needless to say, there will be no second date.

    • Capucine says...

      This! We live in a surf town. Our guy friend, a lifelong surf-every-day guy, was out on a third date with a girl who knew he was a diehard surfer, and halfway through dinner, things were going so well it was clearly moving into relationship territory. He asked her if she liked camping, and her reply was “Oh yes! I love the outdoors! I don’t love getting dirt on me, but it’s ok, really the only thing I can’t stand is sand. I can’t even look at it; sand is my nightmare.” Our friend said he froze, fork in midair, and just stared at her stunned as she detailed her aversion to sand and all the ways she had encountered sand in life. To a guy who is on a beach every.single.day. He said he could think not a single thought beyond, ‘I may as well get up and leave right now’. It was a deal breaker he never knew existed. I can still remember his stunned face as he sat drinking a beer on our patio staring out at nothing – he really liked her, but he could not picture how to date someone who avoided driving near beaches and had a horror of grains of sand in the car or the sheets. He was like, how? I can’t! there is no way to get around that! He was relieved they hadn’t slept together yet, and bummed, and was shuddering at the thought of her sand phobia being missed until much later, and wondered why she would date him in the first place. After that, every first date he went on, he asked ‘Do you have a sand phobia?’ straight out. He did call the girl and talk to her about it, she felt it was no biggie that they not share the beach part of his life but he recognized from that conversation that he wanted a partner who was happy around his beloved ocean. I think, not having grown up in California, she didn’t grok that a sand phobia could be a daily problem that didn’t exist in Iowa. Especially with a surfer. (And weirdly, he met TWO MORE WOMEN who had sand phobias before he met his now-wife! )

  40. M says...

    Omg. This is just too much for me to handle in a silent library.

  41. Karolina says...

    What happened in between? Pray tell!

  42. Joanie says...

    In high school, I was newly dating this guy named Matt and I always loved that his family called him by his full name, Matthew. However, I also had a crush on his best friend, Mike. Somehow I got the two names mixed in my head and one day going down the mall escalator, I lovingly called him Michael by accident! It was like my brain was thinking of Mike, wanted to refer to my boyfriend by his full name (Matthew), and I just blurted out a combination of the two. “Did you just call me Michael????” … “no! I said Matthew! Matthew! Duh??” Absolutely mortified. That relationship didn’t last long, hah!

  43. Anne Elliot says...

    I have two, one that was awkward because I was young, and one that was not because I was older.

    The first one: In my very early twenties I met a guy at a laundromat, he seemed nice so when he asked for my number I gave it to him and when he called to ask me out to dinner I said “yes.” Over dinner I asked about hobbies and he said (verbatim): “I guess you could say I’m a weather buff.” (Me, in my head: WTF is a weather buff?) A weather buff is a half-assed storm chaser who obsessively watches the Weather Channel and bores hapless dates with long stories of the best storms he’s sat through. I smiled and nodded and plotted my escape.

    The second one: I was matched with a guy and met him for dinner and when I ordered a glass of wine he informed me he did not think women should drink. He wasn’t taking the tee-total position that NO ONE should drink (which I would try to respect, if disagree with), he just didn’t think WOMEN should drink. So me and my glass of cabernet went and sat at the bar. My tolerance for male nonsense has dwindled.

    • Jeanne says...

      Ha! Most guys seem to keep pushing drinks at women to lower their inhibitions. How strangely judgmental of him.

  44. Shira says...

    I had signed up for this matchmaking website. I had told the matchmaker that I wasn’t willing to relocate to another city, and she kept trying to set me up with guys who didn’t live anywhere near me. So finally one guy was local. I didn’t think we’d have a lot in common, but I figured I’d give it a shot just because it was the first guy in the same city the matchmaker had come up with. Well. He lived in the suburbs while I lived in the city, and he kept saying how things in the city were so expensive, and he got much more for his money in the suburbs. He had visited a friend in the city before our date and kept mentioning how small the friend’s apartment was. Then he said that his studio apartment was bigger than his friend’s apartment, and that his studio felt like a 1-bedroom because he SLEPT IN HIS CLOSET! He said some other stuff that was also odd, but the closet thing is the one that really sticks out in my mind. It was the only date I went on where at the end, I just said “bye.” No pretense about seeing him again. The funny thing is that a friend of mine ended up going on a date with him through a dating site, and she almost laughed when he said the bit about his closet, because she had heard my story about him!

  45. Lindsey says...

    When I was 17 I had a date with a guy that I was already unsure about. (Bear in mind that this was before cell phones!) So anyway, he’s late. First just 15 min or so, but then a half hour, then an hour – I’m getting PISSED.

    I call my BFF and she says to call his house and call her back. I do and the answering machine picks up. I call my BFF back and I’m code red mad that I agreed to this at all and that he is standing me up. I’m RANTING, with a lot of profanity. “Who does this m-effer think he is?! I didn’t even want to go on this date because I can’t imagine kissing him. From one side he is cute and from the other he looks like a news anchor who has a secret crack problem. I don’t like his nose! He’s always been a dick, really. I’m going to tell him when I see him that he’s an ugly troll -“

    Then there is a loud “BEEP”. I ask my BFF if she has another call. Nope. I don’t have another call. It can’t be. It cannot be that I switched over and three way calling was activated and that was the answering machine. RIGHT?

    He gets there right then. Muddy and dirty. Had a flat tire. So apologetic. So cute with his messy hair. Hey, he says, I gotta call and check my messages to see if my buddy called me back, I called him from the pay phone.

    In my head: this cannot be.

    Him, after dialing and entering his code: wha? I – I AM NOT A DICK!

    Me: It’s been really nice getting to know you, I have to run and throw myself off a bridge.

  46. Jenny says...

    Is this my favorite comments section EVER on COJ? Maybe.

    Newly heartbroken and in the midst of a divorce at 28, I was so sure nobody would want to touch me ever again. I was starting medical school, golden and mean from a candescent summer of fly fishing instead of Eat Pray Love, and online dating for the first time ever in the Thunder Dome that is Palo Alto’s brogrammer scene.
    I match with a handsome blonde man who says he enjoys nordic skiing. So do I! I don’t understand what being a black hatter means– maybe he likes westerns? (It means he’s a hacker.)
    We meet at a soulless coffee shop in swanky downtown Palo Alto. I arrived first, on a bike, to order and pay for myself without the uncomfortable jostle of who should pay. I see him enter, and immediately recognize him as…unusually erect in posture, with a bad shoe-belt combination hinting at a type of unappealing personal precision and premature dad-ness, and a shirt tucked in so, so much that I know we will not get along.
    He sits down. He does not offer a hug or handshake. He says, “Jenny?” And then he gives me a 45-minute powerpoint presentation on machine learning on his laptop.
    Reader, I did not leave because I am from Montana. I am so nice. There are golden retrievers out there meaner than me. And it was a freaking good presentation. I learned so much about machine learning!
    When it was over, I left. Said, “thank you, goodbye.” He followed me to the bike rack and touched my back with a swipe of his hand, between a swat and a jab. I biked off.
    After he texts me, “I’m sorry if I was weird. I’m just not used to being pursued like that.”
    WHAT? Pursued like what? I’m not a ghost (see golden retriever) but I did not respond.
    One week later he texted me my full social security number and nothing else.

    • Anne Elliot says...

      I’m from Montana! High-five!!

    • FGB says...

      Oh my god. What a creep, and also, that’s so funny!

    • Kim says...

      WOW

    • katie says...

      WHAT?!? Your last sentence. Amazing. You’ve left me wanting more. I can’t imagine what went through your head.

    • Oma says...

      this story was so strange! I’m confused/startled that he found your SSN!

    • Melinda says...

      OH MY GODDDD

    • Sylvia says...

      “Reader, I did not leave because I am from Montana. I am so nice. There are golden retrievers out there meaner than me. And it was a freaking good presentation. I learned so much about machine learning!”

      I AM IN TEARS. Laughing for the next weeks about this. Every. Sentence. On. Piont.

    • Christina says...

      This is one for the books! Jenny, you are a STAR.

    • Sarah says...

      Jenny. You can write. Oh my goodness that’s a story but how you told it. Beyond.

    • Meghan says...

      Such a good story.

    • Emma says...

      HAHAHA this had better make the end-of-week reader comments.

    • K says...

      I am DYING over this!

    • Katie says...

      Absolutely dying 🤣🤣 brogrammer! Premature dad-ness! Machine learning! You win.

    • Rebecca G. says...

      So much love for this storytelling! Bravo!

    • Britt says...

      This is amazing. Haha. Definitely dated my share of quirky brogrammer/engineer types. In my experience, they’ve been either very arrogant or odd, but none to this extent. And he found your SSN? How creepy!

    • Ker says...

      Winner winner chicken dinner!!

    • V says...

      I never comment, but just had to say: Jenny, this is amazing, and you are a gifted writer!

  47. Tami says...

    I should’ve wrote a book on dating catastrophes b/c you seriously can’t make this shit up…
    Anyway, the most awkward date in THE WORLD happened to me several years ago.
    I finally got asked out on a dinner date by a guy that I thought could be “the one”.
    I was beyond infatuated with him and spent all afternoon getting ready – the perfect outfit, blow out, mani/pedi.
    I practiced what to say/how to act (I know. But I was in my 20’s people!!) and I could hardly breath thinking about how fabulous the evening would be.
    Fast forward to dinner, I was late b/c I couldn’t decide which outfit to wear and when I finally walked in I was a nervous wreck so I ordered a drink immediately. The hostess showed us to our table and my drink arrived shortly after. By the time I had 2 drinks I was feeing calm, cool, and way more beautiful and sexy than I really am.
    I leaned over the table to cheers him with my 3rd drink in hand and whispered something ridiculous while I gazed into his eyes.
    Little did I know that while I was leaning over the table in all of my drunken sexiness that my hair caught on fire from the candle sitting between us.
    The entire restaurant was engulfed in smoke and everything smelled like burnt hair. I was mortified and we never saw each other again.

  48. michele says...

    This date was not bad, but it definitely took an awkward turn. I was spending the summer in Moscow and a college friend told me I should meet his friend, not as a set-up, just an introduction. So we emailed and agreed to meet for drinks. He picked the bar and said it was quiet and had good cocktails. We ordered a couple of drinks and had a nice conversation, and then just as I was thinking that he was really interesting and we should hang out again, the show started. It turned out that later in the evening, the bar put on a live show. And not just any live show, but a really offensive one, with dwarfs dressed as cowboys and Indians and very scantily clad young women dancing. To my new friend’s credit, he was mortified. He had had no idea the bar also offered live entertainment and apologized profusely. We have now been married for almost nine years and have two kids.

    • Oma says...

      I love the stories that end with couple being married.

  49. Erica says...

    Why are they always named Rob 😂

  50. Meredith says...

    My best worst first date was coffee and a walk over to the local art museum to hang out and chat outside one summer afternoon. We got 2 iced coffees and he pulled out a HUGE wad of cash, $100 bills fanned out everywhere to pay the $7 tab. I knew at that point that this was a dead end date, but like others have observed, I didn’t feel unsafe so I was interested to see how the rest of the date would go. Fast forward to the end of the date, he tried to sneak out! I didn’t realize thats what he was doing at the time, or I would have let him! He went into the museum to use the restroom and I walked inside as well since I needed to get tickets to see the featured exhibit with a friend from work the next day. I realized later that he actually had no intention of coming back 😂 he came up with some story about needing to go rescue a drunk friend in order to wrap things up. The very best part was on the walk back to our cars where he told me all about how he’d recently spent a few weeks in Colorado and then had to order synthetic urine off the internet and smuggle it into a drug test to get a new job…. Lawd!

    • Alison says...

      Does this count as a date story? Sure. I had been dating my roommate for a few weeks (spoiler alert: dating a roommate is a really bad idea) and I was walking home and chatting with my bff on the phone. I walk into our apartment, still on the phone, walked around the whole apartment to see if any of my roommates were home; they weren’t. I keep chatting for a few and walk out onto our back porch which is located at the back of the apartment, opposite the front door. I was on the porch for maybe 3 minutes when I come back inside, flop down on the couch and proceed to YELL to my best friend about how awful the sex is with my roommate. And when I say yell, I mean yell. “HE PLAYS WITH MY xyz AND THAT’S OK BUT JEEZ IT’S LIKE HE’S SCARED OF MY xyz. Nicole, it is SOOOO BAD”. Next thing I see is my roommate/boyfriend walking out of the bathroom approximately 12 feet from where I had been yelling about the horrible sex with him. Guess who had come home while I was on the porch? He gave me a curt wave hello and walked straight to his room and slammed the door. We had to break up, there is NO recovering from that! Even just typing this out, 12 years later I can still feel nearly the full force of awkward.

  51. Samantha says...

    I had always been overweight and self-conscious about it so I would never put myself out there, but in 2015 I saw a photo of myself at my cousin’s wedding and I knew I had to do something. I lost almost 60 pounds and finally had the self-confidence to join a dating website. I started messaging and then eventually texting with a guy who lives in the same town and he asked me to dinner. During dinner, we were talking about our careers and I happened to be working as an attorney for a police department in a bigger city about 30 minutes away. The remainder of our date was him lecturing me about how awful cops are and showing me attorney job postings on his phone. This was not a give and take conversation, but a full on lecture. At one point he got up to go to the bathroom, and the older couple at the table next to me leaned over and said “sweetie, please leave. We’ve taken care of your dinner and we will let him know.” I immediately gathered my things and slipped out the door.

    • Kristin says...

      Aw, what a sweet older couple! And good for you for leaving :)

    • Caitlyn says...

      WOW!! That couple was awesome! I hope to be that couple one day!!! I hate that you had such an awful date, but OMG I love that the couple saved you!!

    • Meghan says...

      What an awesome couple!!!

    • Meg says...

      Awww people are good. May we all aspire to look out for one another like this.

    • Vanessa says...

      Yay! And bless them.

  52. Tiffany says...

    Sigh… I recently had a guy from Hinge ask me out. Despite leaving 45 minutes early, parking was unusually terrible and I ended up arriving a few minutes late after finally finding a spot in a parking lot.

    As someone who is usually hyper organized and has anxiety about not being on time, I burst in through the doors of the bar in a panic and found him saving a seat for me in the packed room. We had barely said hello when I received a tap on the shoulder from the doorman who wanted to see my ID. It was at that moment that I realized that I had left my entire wallet–cash, credit cards, and ID–at home while I was switching out my purse. Despite embarrassingly pleading, “I swear, I’m 38 years old!!”, he wouldn’t let me stay.

    We then decided to meet at a bar closer to my apartment (in a neighboring city) so that I could pick up my ID, but 1) I realized I couldn’t find the lot where I parked and 2) when I finally found the lot, I couldn’t remember where exactly I had parked! By the time I actually located my car, I knew that he was almost at the new bar. I sped up to the gate to pay–only to realize that I couldn’t because, duh, I. Didn’t. Have. My. Wallet.

    I sheepishly had to call him to break me out, as there wasn’t an attendant on duty. He very kindly offered to help me get out of the lot, but since it was nearly midnight at that point–and he lived 1.5 hours away–he admitted that he would have to go home right after that! By the time he arrived, I was completely mortified. He high fived me and jokingly said, “Great date!” as I thanked him and apologized profusely… before flooring it out of the garage in embarrassment.

    And, this is why I’m probably still single. :/

    • Ashley says...

      Oh man hear are amazing. I have only ever dated my husband (him too!) we met in high school and have been together ever since. I know crazy right. So I’m loving these dating stories! This has got to be the best way to experience all these.

  53. Tara says...

    Where to start? I was married and with my ex-husband for 10 years. 2018 I went on my first online date. It was SO overwhelming. And then I thought about interviews, how I am an expert interviewer.

    WRONG approach. These men mostly came from Mars. The book was right. There was man who informed me he had one ball after our first drink. The OOPS, I’m married guy after our second date. The man bun/child who didn’t know what the Me Too Movement was. The list goes on. Each man has a name. The Brazilian, One Ball, Doctor that can dance. I learned a lot about myself and the guy I met on my third date but I kept telling myself I wasn’t ready, we just booked a vacation to Portugal in the fall. These random strangers will forever be hilarious memories.

    Dating can be magic, but mostly it’s full of tears and laughing with my girlfriends and saying WHAT IS THIS LIFE?

  54. Robin says...

    My awkward date story sounds like it’s straight out of a Hallmark movie. I worked as an Interior Designer for a few years in a big Canadian city. It was all very glam: our clients were high-end financial companies and lawyers. Once, after finishing a small project for a firm, my “client” for the project emailed me and asked me out on a date! I thought I might as well take him up on it. He was pretty handsome and clearly doing well for himself. Why not?

    We met up in the chic restaurant of a very expensive downtown hotel. I’d gone there before for drinks with girlfriends simply for the amazing people-watching. It’s the kind of place you’d see a celebrity. After chatting a bit and ordering cocktails, my date casually dropped that he lived in the residential part of the hotel. This was one of the most expensive addresses in the city!

    Then he asked if, as an Interior Designer, maybe I could come up after we finished our drinks and give him my expert opinion on his decor? Yikes. Real smooth, buddy.

    Surprisingly, this wasn’t the end of our date and I decided to roll with it. A bit later, he spotted a friend and loudly called him over to our table. The two of them started peacocking, getting me to “critique” my date’s outfit as he was giving an interview on TV the next day. It was all very macho and I was getting pretty turned off. I decided to extricate myself and went to the washroom to text my friend about how silly the date was going.

    When I came out of the washroom, my phone started ringing. It was my mom and she sounded terrible. She’d just had an attack of vertigo out of nowhere and fallen in her bathroom. My dad was out that night so she was alone. She’d called an ambulance and was waiting for them. She would call me back later when they came. There was no way I could get to her (it’s was a long way from where I was living), but I felt like I had to go home immediately and wait for her next call.

    I was sick with worry, but also stoked that my mom had given me the out I needed. I went back to the table and told my date I had to go home because my mom was sick. He walked me to a cab and without warning, kissed me goodbye on the mouth!! Then he walked away and I went home.

    We never contacted each other again. I still wonder if he believed my story, or if he thought I was just trying to get out of the date. My mom cried laughing when I told her what I had been up to when she called me. Who knows, if she hadn’t had an attack of vertigo, I could be married to him and super rich! But probably not.

  55. I went on a first date with a guy I had chatted with online and seemed nice enough, and we got together for dinner one night at a restaurant. But in person, he was difficult and ornery, and would say things just to be contrary like it was a joke. E.g.:
    Me: I love pizza, it’s my favourite food of all time!
    Him: Oh, I hate pizza.
    Me: Oh! What is your favourite food?
    Him: Pizza.
    Me: ????
    Him: It was a joke.
    Me: Which part? You hating pizza, or it being your favourite food?

    Then our food came, and he proceeded to whip out a needle and INJECT HIMSELF IN THE STOMACH right there in front of me, at the table, without saying anything about it. So of course I asked him what that was about (my exact words were, “I’m sorry, what just happened?!”), and he said that he was diabetic, but just couldn’t be bothered to go to the washroom before eating to inject himself there. And then he got huffy with me, as if I was being judgemental for asking him. But really, what kind of person who would be no-questions-asked if their new tablemate took out a needle and injected themselves without saying anything about it?! We split the bill, and both stalked off into the night, separately, thinking the other was a big jerk.

    • Alex says...

      He didn’t need to go to the bathroom to give himself his life saving medicine, but he could have told you.

    • Bella says...

      Nah, girl, you were definitely the jerk in this scenario. My little bother is diabetic and I hope he never experiences a date like this.

    • Marie says...

      That’s like telling a nursing mom to nurse in the bathroom. He can inject his life saving medicine anywhere he wants. I agree he didn’t sound like a good date, but your insulin comment shows you’re not educated about diabetes (he probably had type 1).

    • Vanessa says...

      I agree with Julie in this case. That’s an eyeful and it’s best to mention it or excuse yourself. I’ve never anyone do that at the table, although I have given those injections.

    • ae says...

      Okay, this wasn’t going well anyway but I think had I seen someone inject themselves right before dinner, I’d know it was because they are diabetic. It’s pretty common and you could’ve responded with any number of more sensitive comments….

    • Sara says...

      My wife is a Type 1 Diabetic and we both agree that this guy sounds like a jerk.

  56. Hannah says...

    I’m cry-laughing at some of these.
    “Aggrandizer” is THE perfect word I never had to describe my worst date, who told me all about how sore he was from his workout that day, multiple times, while rubbing his muscles. I did get a free dinner, he ordered water. So yup, that went well.

  57. When I was 17, a friend of mine (classmate and coworker) came up to me at work and mentioned that he & some of our other mutual friends were going to see the Dark Knight later and asked me to join. I agreed. They all lived in the same neighborhood & I was a little further away, so I drove to his house to meet them and drive to the theater together. I got in his car, he started driving and I asked when we were picking up the other guys. “Oh, they can’t make it.” Hm. When we got to the theater (for the world’s LONGEST movie!!) he tried to buy my snacks for me (no thanks) and then kept his arm on the armrest between us the entire time, clearly wanting to hold hands. That’s when it clicked I’d gotten tricked into a date. I didn’t know what to do with my hands for 3+ hours, and ended up retying my shoes halfway through the movie. Ugh.

    Just a few months ago, a Hinge date asked me to split the bill, even though he’d ordered my drink for me before I got there (his excuse: he’s a med student and broke…so then don’t take me on a date?) Later we ended up at a bar to play shuffleboard where he proceeded to stretch his groin on the shuffleboard table, and grunting that the stretch “feels SO good!”

    • Miranda says...

      I don’t understand – you were mad a guy offered to buy your snacks, then you were mad when someone didn’t want to buy your drink?

    • Stacy says...

      I wasn’t mad in either scenario! These also happened a decade apart. The first story was just an instance of me being a confused 17 year old who was tricked into a date by a friend!
      Personally, I found it a bit off-putting that the guy would order for me and then ask me to pay – I didn’t get to choose what I was drinking! Just awkward for me…not everyone will agree.

    • Shannon says...

      Makes perfect sense to me, Miranda.

    • Sara says...

      What?! STACY these are both awkward AF! :)

  58. Lauren says...

    The silliest one I remember: My mom and I were at a tailor’s shop to get a dress fitted, and there was a father and son duo in there, but I didn’t even notice them, as I was busy with my dress. The next time my mom stopped in the shop, the tailor’s wife told her that the son had expressed some interest in me, and would I like for her to arrange a date for us. I had no memory of him, but I said OK. I was curious, after all. Long story short, I met up with him at a Baker’s Square, and he proceeded to act the entire time as if he didn’t want to be there. So I enjoyed a piece of pie, and then I was out of there.

  59. Cheryl says...

    This happened to a friend of mine, but it’s my favorite bad date story ever. My friend set up a first date through a respectable online site, intrigued in part by the guy’s glowing description of his “family vineyard.” It turned out that the “vineyard” was a couple of scraggly grapevines next to the trailer park where he lived with his parents and other family members in a decrepit mobile home. There was no second date.

  60. E. says...

    Too many bad dates to count them, but the most disappointing: Date with guy who seemed so great in every way. Super compatible. Incredible conversation about any and everything possible. Sweet little butterflies when his hand accidentally touched mine. We laughed and gazed longingly and waxed romantic until the bar closed down. I kept thinking how glad I was that I hadn’t shut down my online profile too soon. I began to wonder if he was the one. So much so that I allowed a kiss on the first date. He began his approach with the gentle delicacy of a starving rat. He pulled my hair so hard my neck snapped back. He dove so far down my throat my lungs had to jump out of the way. He was an appalling and disgusting kisser. Like…no one would have considered this a good kiss. He licked my teeth. Much debate ensued with my friends about whether or not a bad kisser can change and had I been too critical of his technique? I felt it told me everything I needed to know about how the sex would be.

    • Elly says...

      This is exactly like that one episode of Sex and the City where Charlotte dated the bad kisser! Funny to know it happens IRL too.

    • Jenny says...

      E, this is everything.

    • Mouse says...

      Oh dear god. I blame porn.

  61. Diana K. says...

    I had a huge crush on this guy who worked in the woodshop with me in college. It took everything in me to finally ask him out on a date. He seemed really into it, we exchanged numbers and I said I’d send him the details. He must’ve been in the process of looking for an apartment, because EVERY time I tried to text him he mistook me for a/his realtor. Every time he would mention “getting the keys” or something about a deposit, I had to remind him who I was. Somehow we planned a date for Saturday at 3pm. That day I texted him an “on my way” text with no answer. He overslept (!) and texted me at about 5 (!!!!!!!!!) Fuck that guy.

  62. Jess M. says...

    Met a guy from a dating app. I arrive at the designated nice restaurant only to spot him in a death metal band hoodie with a gold rosary. I am neither religious nor into that kind of music. He ends up aggressively massaging my legs and takes me to his friend’s band’s terrible show at a crummy bar where he yells at bystanders to move out of our way. I end up getting so drunk that I fall asleep at the concert and he insists on getting me an Uber. I gave him the wrong address so that he wouldn’t know where I lived and assumed I’d never see him again. I spent the rest of the night laughing about my horrible date with huge loser to all of my girlfriends.

    That was 8 months ago. I’ve never had a worse introduction to someone, nor have I ever been so in love. Not all bad dates are bad ;)

    • Cam says...

      Umm

    • Lily says...

      This is so sweet! Has his massage technique improved? :)

  63. Deana says...

    And one more: Years ago a guy at work I really liked asked me out, and I agreed. When I answered the door, there he was — with another guy in tow, who I also knew from work, and so the three of us went out. Obviously, I had misread the intentions – we were just friendly coworkers. Later, I found out those two were life partners and were buying a house together!

    • Wink says...

      I’ve got a good one for you. In my 20s, trying to be an actor in NYC, I worked at a restaurant called Michael’s that had a lot of industry parties. One night we had a special event for the opening of the movie Panther and the whole cast came, including Marcus Chong, who’d played Huey P. Newton (also: Tank in the Matrix). He was very flattering to me all evening and encouraging to me about my career and promised he’d introduce me to his agent. Sure enough, he took my number and called later that week and asked to meet up. I agreed, honestly thinking it was more of a business meeting. I waited outside a subway station for him nearly half an hour in the cold. It was pre-cell phone days, but I imagine he would have been late anyway. I was, by chance, wearing a beret, and when he finally arrived, rather than apologize, he looked at my hat and said, “Nice touch,” like I was wearing it FOR him as some kind of tribute to his role as a Black Panther. From that moment on it was one non-stop monologue—him talking about the movies he’d done and how famous he was getting, etc. In the restaurant he proceeded to order “one of everything” off the menu and kept hollering—I kid you not—“GARÇON!” at the waiter. He was such an insufferable creep that I was embarrassed to be in such close quarters with him. It was one of those bistros where the diners beside you practically have their elbows on your table. To make a long story short, after the brag-fest and waiter-abuse, he paused for air and mentioned something about our “date.” I then told him, truthfully, that I didn’t date actors and that I thought this was supposed to be a business meeting. “Oh, you thought this was BUSINESS did you? I’ll give you some business.” He then took his arm and swept the entire contents of the table: wine bottle, plates, glasses, food, onto the floor. Then he stood up and delivered his parting shot, “You better take out that little pocketbook, missy,” and stormed out the door!
      I sat there stunned for a minute, then starting crying from embarrassment. A kind woman next to me, who’d heard the whole thing said, “Who WAS that?” She wound up chipping in on the bill!

  64. I went out with a guy I met on a dating app (it was the first time I’d really done a dating app, late 2012), and it turned out in our messaging that he’d even gone to my university — serendipity! He must not be a creep! Anyway, very early on in the date, he told me that while his roommate was gone having spine surgery, he’d rented out his roommate’s room on airbnb, WITHOUT HIS PERMISSION or even telling him about it, just because he wanted to “see what the host interface was like” or Airbnb. When I looked surprised, he added that he “might drop him a hundie” (e.g., *might* give his roommate a hundred dollars). I still looked surprised and he seemed confused as to why.

  65. Katie says...

    I went on a date with the same guy twice. The dates were spaced out by about 4 months. I had unmatched and then (evidently) re-matched with him on Tinder. I thought he looked familiar in his profile, but at that point in my life, dating was a part time job, and I guess I thought we had just texted before but never met up. Oh my goodness. As soon as he walked in the bar, I knew. The big questions then were 1) Will he remember too? and 2) If he doesn’t, should I say something? He sat down and clearly did not remember me. I took a sip of my drink and then quietly said, “We’ve met before.” He was totally surprised. I recalled our last date with enough detail that it finally rang a bell. (It had been pretty unforgettable…we’d both forgotten about it! Beers at a sports bar while a football game was on. So not me. So weird that it even happened.) So! Then we decided to have fun and make the most of it! We did! We had a couple drinks there and then grabbed a couple more down the street. Nothing happened, and I never saw him again. Nice guy, though.

  66. Alissa says...

    After cheesecake with a thrice engaged, twice messily divorced felon (all learned from a monologue response to the question “Have you ever been married?” after I’d done some internet sleuthing pre-date. Thanks MySpace!), I had planned to head home and tell everyone I knew about the date from hell. Instead, I was so thrown off by his suggestion of a movie that I agreed. Next thing I knew, we were at Knocked Up and he kept whispering the parallels to the accidental birth of his first born. When a few days later he suggested via message that we go out again, I politely declined and received a pleading missive in return. He wrote that I’d listened better than anyone he’d ever met and that he thought I had potential to be wife number three. Reader, I did not marry him.

    • Alyce says...

      “Reader, I did not marry him.” Maybe the best line ever. So hilarious!

  67. Veronica says...

    I met a date for the first time at a fancy restaurant. Seemed handsome, professional, normal. The hostess guided us to our table, where an older couple was already seated. This must be some mistake. Nope. Turns out … they were his PARENTS. HE INVITED HIS PARENTS ON A BLIND DATE WITH US. Did I stay? Yes. Why? Not sure. I was too frozen. Too awkward to leave. They paid for his bill and my salmon. Sometimes I wonder how Dave and Cindy are doing …

    • Alanna says...

      Omg that’s crazy!

    • Oma says...

      Veronica, this made me laugh/

    • Jess says...

      Hahaha that is HILARIOUS

    • Amanda says...

      I gasped reading this. THE AUDACITY!! I would have stayed, too, honestly. The story you got out of it was well worth it :)

    • Kim says...

      This is everything. Thank you for sharing.

      My most awkward date was with a guy I met on Bumble who, when I met in person, was clearly 10 years older than his picture. He told me his heroin-addicted brother was living with him, and I believe he was on heavy drugs as well. We were at the loudest bar I’ve ever been to, and somehow, he was speaking so loudly everyone was turning to stare at us. He kept yelling out random things like “IM NOT READY TO BE A FATHER” like I had asked this weirdo to make a baby with me. His laugh was maniacal. He went to the bathroom and I met a bar angel who helped give me the courage to tell him I needed to leave. I told him I was having anxiety (pure panic on the inside) and wanted to go home for the evening, and he thought that was perfect, because he had mental health issues too and we could “fix each other.” I did a light jog to my car.

    • Sarah says...

      OH MY GOD

    • Laura says...

      oh my gosh! you’re a trooper.

    • Roxana says...

      OH MY GOODNESS. THIS IS GOLD. I cannot stop laughing!!!!

    • Jess says...

      Someone help me breathe I am laughing so hard. This is the best comments section ever on CoJ

  68. I was talking to a guy online and we were trying to set up a time to go on a date. The problem was he was starring in a play in a small town theatre, and was busy every night for weeks. So, he invited me to come see the play. I said “what the heck” and went by myself. When I arrived he told me to pick up my ticket at the front desk. The woman was VERY excited to see me (“Are you Tori?! Do you like theatre?!?!?”) and after I retrieved my ticket I watched a great production of The Producers (my “date” was an excellent actor/singer). Afterwards I waited to introduce myself to him in the lobby, but this being a small town, he being the lead in the play, and it being opening night, he was hard to get to. When we finally started chatting I noticed an older couple lingering in the lobby who were also waiting to talk to him. He kept looking over at them and they finally came over. THEY WERE HIS PARENTS. And his mom was the one who gave me my ticket. We went on a couple more dates, but it fizzled out quickly. But I have this story now :)

    • Andrea says...

      Were their names Cindy and Dave?!?!?

    • Neela says...

      Andrea, lol!

    • Elly says...

      Aww that’s really sweet. Reminds me of Andy from The Office.

    • Megan says...

      Andrea, I just laughed so hard. God I hope so!

    • Helen says...

      Haha, Andrea! I really hope it was Cindy and Dave!

    • I don’t remember their names, but I will certainly think of them as Cindy and Dave forever more!

  69. Christine says...

    It was the late 80s. I was 17 and had a mad crush on P (18!) and he had finally asked me out. I had just started to “date” so did not really know what to expect. P was sweet, charming and so stinkin’ cute. We went out for dinner and I saw him peaking at me over the menu and we smiled. SWOOOON. “What are you getting?” “No. What are *you* getting?” (I’m cringing as I write this..is this even conversation??). But seventeen year old me was over the moon. I don’t remember dinner, I only remember floating with joy. I wished the date would have stopped there because it was everything my seventeen year old self ever dreamed of….

    Then P drove me home, stopped in my driveway and leaned over to kiss me and then…

    he farted.

    I was paralysed with both excitement (my crush was going to kiss me!) AND fear because WHAT WAS I SUPPOSED TO DO NOW?!?

    I remember time being suspended after *the fart* and I just sat there frozen looking straight ahead… it felt like forever. Maybe if I don’t say anything he’ll think I didn’t hear.

    He then turns red and says “Oh my god I’m so embarrassed please don’t tell anyone”.

    I’m like, “uh, okay”.

    I think he apologized again a few more times – so much so that seventeen year old me thought it was sweet, him apologizing so much (what was I thinking?). I want to think I tried to hold my breath (did he lower the window? Gosh I don’t think he lowered the window!) but honestly I don’t remembering it smelling that bad. Lol. See? Love messes with your senses!

    I don’t think we kissed that night and I can’t even remember how the date ended but I went home being pretty confused about a pretty awesome date where/but he farted.

    • P says...

      You promised you wouldn’t tell Christine!

    • Renee says...

      On my second date with my now husband he was checking something
      In the oven when I bent down to look in the oven I farted. I think he just played it off. I was mortified! And here we are all these years later…

    • AK says...

      To the person who responded as “P Says” you’re brilliant.

  70. Deana says...

    Another story: I’m female, and a woman I had worked with on one occasion suggested we have dinner out sometime. I agreed. During the dinner, I began to realize she considered it a romantic date, but I’m not gay and had to tell her that. Awkward, because I liked her, just not in that way, and had no idea she was gay – she had a husband and child. On the “date” she’d brought a portfolio of her artwork, mostly female “full monty” nudes and offered to paint me like that. I declined.

    • Louise says...

      My worst date was with a guy I started chatting with on MySpace (YEP). He suggested we meet at a restaurant that I didn’t really like, but he stressed that it was affordable. When I met him at the restaurant I thought he was cute though dressed a bit dorky. The meal was painful. He was so shy that he could barely look at me. We had very little in common. I saw him one other time after that which was even more awkward, so I stopped talking to him. Except a month later we reconnected and we got to know each other very slowly. We will be married ten years in November and we have two children. He’s the kindest person I’ve ever met, even if he didn’t have a clue who Stephen Colbert was on our first date.

  71. Elena says...

    This EXACT SAME THING has happened to me! Except I didn’t realize it… and I spent the whole accidental date telling boy-Reagan-who-had-texted-me that I was just waiting for my-friend-Reagan-from-the-basketball-team. He was really nice about it, but I finally put it together twelve hours later in one of those horrible moments where you sit up in bed and gasp.

    • Allison says...

      This is so terrible and wonderful!

  72. Jeanne says...

    In college, I got set up by my parents who were dying for me to date the son of their friends, who was some big wig doctor. He was a decade older than me and I wondered, why doesn’t this guy have a girlfriend already?The dinner was a like a job interview for a position of “Wife”. What was my fashion sense? How would I behave in a corporate social gathering? The kicker was that he wanted to know what I would do if my husband CHEATED ON ME. I told him that the marriage would probably be over. You’d think that would be the end of that but he then went into a debate over why it was better if a husband cheated on his wife than the other way around! Needless to say I was completely disgusted. We had to attend a tennis match afterwards and were seated super close on benches. Every time his knee touched mine, even by accident, I moved over. When he took me home, he asked my mom if I was on my period because I was so testy. Ha!

    • Katey says...

      Calling this guy a pig is unfair to pigs. What a misogynist!

  73. I have so many, but the latest still makes me cringe.

    It was our second date. Our first was fun, super casual, spontaneous and flirty, not at all strange. Something had happened to this man between the first and second date to make him EXTREMELY nervous and awkward–within 10 minutes of sitting down for dinner, he joked about not wanting to walk down the aisle (!!!) at our wedding (???) to AC/DC when I said I liked classic rock. Later, he said that he’d already told all his friends how much saner I seemed than his last girlfriends.

    He repeatedly tried to make plans for our third date while on the second date, even after I suggested we just take it easy and enjoy the moment. Later, I had to politely tell him that I preferred to kiss with less tongue (a problem I’d been anticipating since date #1 and I’m still proud of myself for speaking up–ack!) but when he pulled up a saved screenshot of my Bumble profile picture and announced he could tell I was wearing the same boots in that picture as I was on our date, I was prettyyyy much done.

    The final straw? The comment, “Haha, I can see you’re pretty independent! But by our fifth date, you’ll be doing everything I say! *wink*”

    There was no fifth date–there was no THIRD date either, obviously. While the anecdotes are amusing individually, this whole scenario makes me really glad I’m a trust-my-gut kinda girl!!

  74. Alyssa says...

    I’ve done a lot of online dating (thank you Lord for a wonderful boyfriend who I will eventually marry and that that phase is over! Amen.) through the years.

    Early on in my match.com days, I had talked to this man named Chris. We messaged for awhile, longer than I normally talk before exchanging numbers or setting up a date. We had planned and cancelled a first date a few times but eventually decided to meet up at a local coffee shop.

    I arrived second and texted him to ask where he was and he said he was there. When I went into the coffee shop, I couldn’t find him anywhere. It’s decently big, but not like impossibly so. Eventually he texts that he is outside on the bench out front. From inside looking out, I see a man who couldn’t possibly be him because he looks 100% different than his pictures. His hair was so bleach blond that it was actually see through. I have enough decency to not run, but I wasn’t attracted to him.

    We ordered food and sat waiting for it. He wouldn’t talk to me. If I asked him a question, he’d respond with one or two words. He wouldn’t ask me any questions. I tried to engage him by asking any question I could think of. But he barely spoke. Luckily eating food meant we could put food in our mouths as an option.

    I made up an excuse to leave early because it was painfully awkward. I left and thought that it was all done.

    That night, I get a text from him saying how much he enjoyed our date and wanted to go out again. I politely declined.

    • Elly says...

      This reminds me of a (female) friend of mine. She’s soooo chatty over IM/FB messenger, but then you have a meal with her in person and she just sits there smiling at you. I have to do all the work making conversation. I don’t get it!

  75. In college I went on a blind date with a guy who turned out to be so profoundly awkward to talk to that I excused myself to the bathroom and then just snuck away and left. Admittedly this was the wrong thing to do, which is why it may be no surprise to you that karma kicked in and gave me a flat tire while pulling out of the parking lot. He saw me out the window and then joined me to help change my tire. Please know that living with this memory is punishment enough.

    • Amanda says...

      This wins.

    • Neela says...

      Wow, that could be the *definition* of awkward!

    • Anna says...

      Omg!!! Sorry, this made me laugh. And cringe:

    • Lily says...

      I’m cringing for you! But…at least he was a nice guy?

    • Jenna White says...

      I am actually laughing out loud at my desk

    • Calla says...

      nononononononono I can’t even handle this. Dying inside. Thank you so much for sharing.

    • Rebecca says...

      Actually crying with laughter! So well told.

  76. Mags says...

    This wasn’t an awkward date but the name mixup reminded me …

    When I was in the fifth grade the thing to do was “go out” with someone you liked — which really didn’t make sense as a term because we were in fifth grade and couldn’t go anywhere. Anyways, one morning one of the guys in our class asked me if I “wanted to go out with Joe” (he was next to all of the other guys in our class, so Joe was standing next to him). I was shocked as I was awkward and unpopular and never expected to be asked to go out with anyone (even through a friend). Problem was, there were two kids named Joe in my class. Both Joes were nice, cute, and more popular than me (which were pretty much the only things I thought that mattered in fifth grade) and I had at one point or another had a crush on each of them (and currently had a crush on one in particular). Still, I said no because I couldn’t get up the nerve to ask which Joe was asking me out. I still sometimes regret that decision (especially since it was 9 years before the next guy asked me out). I also sometime wonder how Joe felt about my rejection.

    • Kristin says...

      Oh man, your story totally reminded me of 6th grade… A boy in my class liked me and had one of my friends ask me if I would “go out” with him. He was cute and seemed nice so I told my friend to tell him yes. After relaying my message to him, the friend came back and told me that he wanted me to go home after school and write a list of all the things I liked about him. Dumped him on the spot!

  77. anne says...

    I heard recently about the classifications of fun from a friend whose dad is a comedian. Type 1 fun is the sort of fun that is fun while you are actually having it, Type 2 fun is the sort of fun that is not fun at the time, but is very fun to tell people about after it happens. I am really enjoying this giant pile of type 2 fun!

    • Leanne says...

      We call it “retrospective fun.” A lot of family vacations are like this – harrowing while you’re in them and magical memories when they’re over – “we had the best time!”

  78. Linnea says...

    Oh wow. I have so many, all from online dating at various times. Some highlights:
    -This one was years ago. I had an online date planned; I confirmed the day of, and he replied while I was on my way to the date that he forgot and asked to reschedule. On the reschedule day, he told me he forgot to pick a place. No big deal– I picked a place, and then he showed up 20 minutes late. He then proceeded to imply that not only had I gotten my job through luck instead of really hard work, but also the field that I’m in (NGO world) was harming people and then proceeded to berate me the entire time. I don’t know why I didn’t get up and leave.
    Cue to several years later:
    -on a date in an amazing, and very tiny, Vietnamese restaurant. Date tells me he never wants to travel to Asia because it’s too crowded and because it sounds like people are shouting when they speak to each other, and he then proceeds to (loudly) imitate sounds from Mandarin.
    -Had just moved back to the US after several years living overseas. Was told that being on an online date so soon after moving to the US was “desperate”.
    -Went on ANOTHER date several days later, where the gentleman in question showed up 30 minutes late, told me all about how he doesn’t like his job, wants more respect and money at work but doesn’t want more responsibility, but his talents are really underutilized so he hates his job, wants more respect, etc etc. and did not ask me a single question the whole time. Nor did he offer to buy me a drink in exchange for the free therapy.

  79. Allie says...

    The date was bad. Went home, stripped naked, and sprawled out in the bathtub. Turned on the shower. Ate my leftover steak with my hands. Gnawing on it, like beef jerky. Water streaming down over my body. And over my steak. Turns out, wet steak is still, in fact, pretty good.

    • Lenna says...

      Yes Allie!

    • Simone says...

      😂

  80. Dee says...

    A congressman asked me for dinner three years ago. Considering that I work in public service, I thought he wanted to exchange policy ideas and saw the dinner as nothing more than a professional dinner with a colleague. It wasn’t until halfway through dinner that I realized we were on a date. When the check came, and I gestured to include my debit card with the bill he said: “does it mean you are taking me home if you pay?”… I hugged him goodbye after dinner and texted him telling him I looked forward to our professional relationship. He invited me out again one year later, I met him for dinner again believing it was a professional dinner, but nope. Fast forward to today, I can finally say that he got the message, and we have worked together without any awkwardness.

  81. Sasha L says...

    Not criticizing Caroline’s behavior here, but I feel like I’m being smacked over the head lately with examples of women’s compliance, and it’s making me a bit crazy. I want to support all of you in saying no and walking off. Just another scenario: Caroline walks in, realizes this is the wrong Rob, so walks over and explains to Rob that she’s made a mistake and also that no, she doesn’t want to go on a date with him. Turns around and walks out.

    If your boss *requires* you to attend an office pool party, in a bathing suit, no, you DO NOT have to attend, or wear a swim suit if you do. Nor do you owe an explanation for your no. (True story)

    Can we practice with each other, where we feel safest, saying no, foregoing excuses and apologies, can we stop suffering through things that we simply could’ve declined, can we kick compliance to the curb? It’s not serving us. And our daughters are watching and learning with every excuse and apology and “I don’t want to but……”.

    • Calla says...

      Very true, but so so hard to pull off in reality (especially in a situation like Caroline’s where you only have a few startled seconds to correct the mistake). You are right that practicing is probably a good idea.

      I’ve definitely been on a lot of dates (and from the comments here I am not alone) where I knew within seconds I didn’t want to be there and yet I stayed, sometimes even for a second drink, because I didn’t have the words to just walk away.

      At the same time I feel like it is OK to just stick it out, especially if you feel like boring conversation, open-mouth eating, etc. is going to be less unnerving overall than risking someone’s anger and insults if you walk out. Not the way it should be necessarily, but sometimes that’s just what feels safest.

    • Emily says...

      I understand your perspective, but I also feel that it’s important to be kind. If you are mistaken, and the guy came there in good faith, then what is the harm in having a drink? Unless you are uncomfortable or feel unsafe, I think it’s laudable to do the kind and polite thing even if it’s not 100% your preferred scenario.

    • Kiersten says...

      Sasha L, you have encapsulated EXACTLY the sinking feeling I had while reading all these comments. Like I knew they were supposed to be “ha-ha” funny but I just found most of them equal parts sad, anxiety-inducing and disheartening. I even felt angry on behalf of some commenters (that girl who was ambushed by the ribbon-wearing albeit fully dressed professor was a perfect example, as was the girl who had the semi-famous pseudo actor/100% creep sweep all the dishes off the table and stick her with the bill for all the damage HE did). I’m not saying this as another way to blame women for the bad/awkward things that happen to them — far from it! — but I AM mad that women have been conditioned to be “kind” and “not cause trouble/kick up a fuss” or not do what they wanted to in the moment (walk out, not agree to continue with the date, etc) for fear of incurring the wrath of, or violence from, some entitled male a-hole. I say this as a woman who was (and still is) a people pleaser all through my 20s and 30s; who believed/thought that minimizing my own discomfort was easier/better than prioritizing my own wants or needs, even in this relatively low stakes scenario (dating as opposed to dealing with a bullying boss where your career and livelihood could be at stake, for example). It’s hard even now to stand up for myself, even though now I know that I am perfectly within my rights to do so. It’s just maddening that even coming to the realization that I don’t have to prioritize other people’s feelings at the expense of my own took so darn long. So much time was wasted trying to undo the conditioning of society. The thing is, it’s still a constant struggle. I wish we could all just collectively give ourselves permission to just say “nope” and walk on out of whatever situation makes us feel uncomfortable or tricked or vulnerable. It doesn’t have to get to a point where it’s properly alarming before we feel like we can be granted a free “get out of this date” pass. You don’t owe any would-be date your time, energy, presence or attention, ladies!

    • Tasha says...

      Sasha I’ll pick the right thing over the kind thing any day of the week!!

  82. nora says...

    I had recently (and finally) had some sparks fly with a guy (from work) I had been doting over for months, but already had a date planned with someone else a couple of days later. It was a friend of a friend that I kind of knew so decided to at least meet for a drink, and my new spark buddy said he didn’t mind. I got home from work and called said date to let him know I was running a few minutes late and he replied, “no prob, do your thang thang.” That uttered sentence realllly annoyed me. Wtf is “thang thang”?! We had one weird drink and called it a night. I ran to meet spark buddy at a different bar and said, “I don’t think I can go on a date with someone besides you anymore.” I ended up marrying him.

  83. Ray says...

    This is my go to bad date story that I live to share: From the dating apps I agreed to go on a date with a handsome, dog-owning, motorcycle riding guy named Patrick. Patrick checked with me in advance and asked if I wanted him to pick me up on his motorcycle. Young me clearly said yes. Then Patrick was two hours late for our date on a Wednesday night. When he arrived I walk outside, and he does not take off his helmet nor does he get off his bike to greet me. He simply flips up his visor and says, “Hey. Have you ever ridden a motorcycle before?” Be still my ever beating heart.

    When I said no all he did was hand me a spare helmet and told me to hop on. I regrettably did. Sorry dad – at least I wore a helmet! At the bar I order one drink and suffer through painful conversation. At one point as Patrick is mainly watching a hockey game on tv he says, “I don’t know why I’m watching this. I hate hockey.” And then kept watching. I soon thereafter ask to go home. Not five minutes later after I was dropped off (did he even leave yet?) I get a text asking, “Were you trying to invite me up to your place?” I had not yet developed my feminist NO voice and texted back some vague version of not really. To which Patrick thought he should explain to me, “You should just be blunt and say hey Patrick I want to suck your d***” To which I replied, “noted” hoping sarcasm would win out. When it did not get through he tried one more time, “Well do you?????” To which I finally managed to say “Absolutely not.” I’ve been working on voicing my absolutely not responses loud and clear ever since.

    • Calla says...

      Oh my gosh that sounds terrible! I can totally relate about believing (incorrectly) that guys like that will pick up on sarcasm.

  84. TJ says...

    When I was in 10th grade, an older guy asked me to Homecoming. For some reason, I accepted the invitation. When he picked me up, some other girl was in the car too. She proceeded to join us at dinner and then, at the dance, my date disappeared, only to return to me after the dance, with his arm around the aforementioned girl, to ask me if I needed a ride home. Again, for some reason, I said yes (I should have walked), and the girl joined us on our journey. It was just so weird.

  85. MM says...

    I did a whole lot of online dating in my 20s, and went out with a guy once who was maybe a little quirky, but was SUPER cute (he wore cowboy boots and was NOT ridiculous in them … a rare sort). So, on maybe our second or third actual date, we had dinner at his apartment, and after a makeout sesh, he goes, “I want to put you in stocks.” For a second, I’m like, you want me to … invest in a mutual fund? Oh no, friends. Like, actual stocks – i.e., the historical wooden torture instrument you saw in village squares, where they lock your head and hands up. I was like, ” … I don’t think so.” We parted ways for good that night – different tastes, clearly – but before I left, I was so curious, I couldn’t help it … I asked to see the stocks :)

    • Kim says...

      KINKY!!

    • Kristin says...

      DYING! hahahaha

  86. Calla says...

    This reminds me of a time my (straight, female) friend met a really cool girl at a concert and invited her out with us for drinks the next weekend. While we were waiting for her, a (male) acquaintance of my friend who happened to be at the same bar came over to say hi and then started being kind of clingy. He was making us uncomfortable so we kept trying to lose him by moving to other places and letting the girl know where we were, but he kept finding us!

    At some point we texted her that we were up on the rooftop. The guy was standing with us at that point, and when his phone pinged he asked us why we were telling him where we were, since obviously he was right there.
    Horror of horrors!

    It turns out my friend had given her number to TWO people that night, and when this guy texted her the next day to say “nice to meet you” she mixed them up. The poor guy had been invited and couldn’t figure out why we kept ditching him and then texting him. Definitely a good reminder to both confirm names from new numbers and not feel pressured into giving your number to someone you don’t really want to hang out with.

    • Kim says...

      I had been casually seeing a guy for a while (but I was really, really into him) and he offered to pick me up from the airport after a trip I took. I agreed and he picked me up dressed up very nicely. I was over the moon! He took me out and it was a great night.

      Until later that night he admitted he’d gone on a date before picking me up! I was so upset and I basically let a bomb of my feelings about him off. He seemed surprised and took me home sort of abruptly. I was pretty upset at the situation, mad at myself for both holding my true feelings in and also at over sharing them and ruining the date. I felt like a fool.

      The next day he called and asked to meet up for coffee. He told me he’d thought about what I said, and he asked if I’d give him another chance and date exclusively. We celebrated our 7th anniversary yesterday!

    • Kim says...

      Whoops! Didn’t mean to make this a reply to your hilarious story!

  87. Mara says...

    When my [now] husband and I were on our first date at a Thai restaurant, I knew I’d get insane gas from the food, and decided on a double-whammy Gas-X and Beano combo. I even had them ready to go in a nondescript pill jar. My hand somehow slipped and much to my horror, Gas-X and Beano bounced and spread out all over the table (and by the way, Gas-X really has a bounce to it). It even bounced into the food. Worse, the spectacle alerted some nearby diners who instinctively reached down to pick up the green capsules and examine them/hand them to me. I love that my husband’s one memory of that night was not how excited he was, or how beautiful I looked, or that freakin’ Real World was filming literally across the street at that very moment. Nope, it was about my gas.

  88. Karina says...

    I once went on a date with a guy from NZ. Friends set us up and I thought okay, maybe they see something I don’t . We went to a Chinese restaurant and I can’t remember much of the date as his eating habits were so awful. I am not talking about not being able to use chopsticks here but he literally shovelled huge amounts of food into his mouth. We had a table in the middle of the room and literally everyone was watching him. I don’t think I ate much. I don’t think there was much left either. And the only bit about the conversation I remember was him saying that he was going to get himself some dirt when back in New Zealand. I had no idea he was talking about land! I definitely did not want to go and live on his dirt with him so there was no second date.

  89. Allison says...

    I did something really similar to this! In college I texted a guy named Brian to meet up late Saturday night to hang out. We used to hang out in his dorm room and smoke pot after going to the bars, ha youth. It wasn’t a romantic relationship at all. The Brian that showed up in the dorm lobby was a totally different Brian, he was in one my classes and we were assigned to a small group together, so I had just gotten his number to coordinate an assignment. I realized it looked just like a booty call, and I was too embarrassed to say I had texted the wrong guy. He led me directly to his dorm room, where I made awkward jokes and small talk for way too long before making some excuse to leave. He was clearly confused, I should have just explained it up front!! The rest of that group project was incredibly uncomfortable.

  90. ANDREA says...

    How about a surprise date? I had gone to an event and was chatting with two guys. We talked about where we worked. Fast forward to a week later where the odd guy emails me at work and then shows up to the company Christmas party. I guess he also knew someone at my company and crashed our party, circling the room looking for me (as he later emailed me). Ugh! Thank God for a work friend who literally acted as a human shield at the party until I could slip out.

  91. Lora says...

    I have too many bad date stories to choose one but I’m loving reading everyone else’s version of this life experience!

    Reminds me of the bad date with Nicole Kidman and Jimmy Fallon: https://www.youtube.com/watch?v=qtsNbxgPngA
    So, so awkward. “And then you put a video game on or something.” hahaha

    • Lauren says...

      His face around the 1:15 minute mark when he realizes what happened. I AM DYING.

  92. Alli says...

    I have such a good one for this….
    A few years ago I went on a really fun date with a tall, handsome 28-year-old names Steve. He was very complimentary and after we finished our food he asked me to walk around the corner with him to a little bar, and then after that a *second* bar. I am pretty careful to give people plenty of outs in case I’m reading the situation wrong, but he was just as into the date as I was! So the 1-hour plans we’d made turned into 4 hours of laughing and flirting. Then, as we were leaving, I said in a kind of flirty way “So….will I hear from you again?” (embarrassing, but I was so sure he’d say yes!) and he replied “Well, actually, I just don’t think you’re someone I could see myself with.” I audibly laughed because I thought it was a joke, and then I was heartbroken — how could this be real when we’d just had such a great time?! He made these serious eyes at me, held my hand, and reasoned, “I want to end up with someone who, if we woke up in the middle of the night and heard coyotes outside, she would pick up her shotgun and go outside and hunt them down. Do you think you’re that kind of girl?” He was dead serious. I was FLOORED. We live in downtown Atlanta, with no coyotes for miles. Hahahaha.

  93. Sarah E Kim says...

    First date with a guy I met online. Lied about his height – he was an inch shorter than me WITH heeled dress shoes. Then about 90% of the dinner conversation he spoke and talked and talked and talked about football. Football this, football that, how he coaches football for a local league, teams he loves, how much he knows about it etc etc… Funny thing is, he never even played football himself in his entire life. ??? Then at the end, he walked me to my car and held out his arms wide open like, “Grrrrrr come on and give me a bear hug!!!!” … 😖

    • Ll says...

      LOL I had a similar experience with a guy I met online. He said he was 5’9” and honestly I don’t really care (I’m 5’7”) so never asked or commented about it. Date day comes, we meet and he is.. shorter than me? MUCH SHORTER. I was a bit baffled as WHY lie about it as it would be obvious when we met? I let it go and we start talking, and conversation is good so I stay. We have a beer (he pays), then another(I pay) and when he asks if I want a third one I say no as I have work in the morning. “But you go ahead if you want another one” I claim. He then goes awkwardly: “I do want another one but I didn’t bring anymore money”. I buy him a beer and leave. He texts me and thanks for the awesome date and ask for another one. What. I obviously said no.

  94. Elizabeth_K says...

    I was dating after a 5 year relationship and went online to meet people. One guy was so funny in emails — it just felt like a hilarious, perfect match. We met for lunch in D.C. and started sharing our stories. He told me he and his ex-wife had three children together. And that she still home schooled them, at his house. And that she had actually just moved out. And then he started crying. When I gently suggested that perhaps he wasn’t ready to date yet, he cried harder and said, “But SHE’S dating.” We didn’t see each other again. (A few years later, I saw his column in Modern Love in the NY Times. I was glad to know he did find love again …)

  95. amber marlow says...

    This happened to me! I was flirting with Chris F via text but picturing Chris S. Finally he said “why don’t you just come over?” He gave me his address, and I got dressed up and cabbed over to his house. When he opened the door, I composed my face pretty quickly.

    We totally had sex.

    • Sara says...

      Bwahahahaha

  96. Deb says...

    Back in the 70s I was a very young Canadian OB nurse at a hospital in New Orleans. A new medical student started a rotation in our delivery unit, and asked me on a date. He picked me up in his little car, and off we went to a pizza restaurant. At a stoplight along the way, he leaned over to kiss me (!!!) even though we barely knew each other. I was shocked, and instinctively turned my head away. He was already leaning way over toward me and he leaned even farther down and bit my leg through my jeans. REALLY HARD! I was speechless, and we continued on our way to the pizza place as if it had never happened. After our date, he returned me to my apartment and we never spoke again, even though he worked in my unit for another few months. The bruise his bite left on my leg was the blackest bruise I’ve ever had and lasted for over a month. It showed through my thick opaque white nurse’s stockings. What did I do about it? NOTHING. To this day I shake my head and wonder why I continued on the date, and why I didn’t say anything then or afterward. Then I remember it was the 70s and I was 20 years old. And that makes me so sad.

    • Rachel says...

      I’m so sorry Deb. That’s horrible!

    • Breamons says...

      WHAT A WEIRDO!

      Honestly, even though this is years later – I’m very glad that you’re okay.

    • Gus says...

      This is such a crazy story! Many women would have done the same thing at 20; I probably would have even though it’s depressing to admit. It really makes you wonder who raised a guy like that.

    • Alli says...

      Oh. My. Gosh. How completely horrific. I’m so glad you told this story on here. Thank you.

    • Agnes says...

      Deb – you’re not alone. When I was in my 20’s, in the 90’s, my work colleague came over and bit my bum through my uniform pants. It too left a bruise and bite-mark, right on my butt. He said he ‘just couldn’t help himself.’ I didn’t do anything about it either!! I didn’t want trouble at work! Those were the days right!?? Ugh!

  97. Amy says...

    I was set up with a guy in high school through a mutual friend, and after talking with this boy on the phone for a few weeks, we decided to go out. We went up the canyon with another couple, and found an awesome fire pit in the beautiful Utah mountains. We were having a great time, roasting hot dogs and eating s’mores . . . A seemingly perfect first date by all measures.

    As we were cleaning up to leave, I suggested putting out the fire with left-over Apple juice from our dinner.

    My date said “no worries,” and then proceeded to whip “it” out and pee on the fire.

    Then he tried to hold my hand, after not washing his own. Um . . . no.

    • Bonq says...

      😂😂😂

  98. Meg says...

    This isn’t a first date story, but my boyfriend and I once invited his (conservative, religious) parents to see the play, Angels in America . BEAUTIFUL play, but so awkward as it’s focused on what it’s like to be a gay man in the 1980’s AIDS crisis. Wheeee.

  99. Carolyn Gan says...

    Licked my entire face when saying goodnight.

    • Emily says...

      LOL what?? That is so gross.

    • Deana says...

      Just like the psycho killer character did to Sandra Bullock in the movie Murder By Numbers – yuk!

    • Alli says...

      WHAT! Hahahahaha.

      Oh, I’m so sorry. And I also can’t stop laughing.

  100. Maclean Nash says...

    On a ferry boat heading back home, a cute guy asked if I wanted to pass the time and play a game of cards! We shared names and pleasantries and learned we had a lot in common. I.Was.Thrilled! This was just before the prevalence of cellphones and facebook and I was 14 and he was 16 so we just verbally agreed on a location to meet up the next day in the city for a date.
    When we met up, I saw him, and happily exclaimed, “Jack! Hey, how’s it going?” He looked at me confused and LITERALLY TURNED to see if I was greeting someone else behind him. I thought he was being funny so I repeated, “Chak, how’s it going?” When he registered I was definitely talking to him he said, “My name is Chak. Not Jack. CH-CH-CHAK! CH-CH!” as if I was the biggest buffoon ever for hearing “Jack” when he introduced himself.

    Being 14 I was mortified and wanted to melt into the ground.
    After the awkwardness we went to a restaurant and shared chocolate fondue. I vividly remember feeling so mature and thinking, “wow, this is just like the movies, this is what dating is”.
    Now, being 26, there has not been another time where I have, or wanted, to share fondue with anyone, especially a first date – the double dips, the inevitable chocolate on the chin, the drowning piece of angel food cake that you have to rescue with your fingers. I did learn however, to always repeat names and make sure I have it right the first time round.

    • KM says...

      I went out with a guy 2-3 times thinking his name was Shea. His Boston accent was so thick that his name was actually J.R. , which I somehow eventually realized without asking him point blank. He also needed me to pick him up because his license was suspended for a DUI. He was really nice though! Haha, ahhh youth.

  101. Lauren E. says...

    Oh god, I have so many awkward date stories.

    The worst was when I went on a date with a guy who SHOULD’VE been great (owned his own neighborhood pub, had a dog, super cute). We got to the restaurant for dinner, he asked if I liked sake, I said no, he ordered a whole bottle, and then drank it all himself. He talked about himself the ENTIRE date, getting more and more outspoken the drunker he got, and then as he walked me to the train, asked if I wanted to get another drink. I said no thanks and he screamed out (IN THE STREET), “So what did I do? Huh? I must’ve done something wrong! So what is it? Just tell me!”

    And yes, of course he called to go out again. And then a year later, called AGAIN.

    • Tori says...

      I’m sorry for your bad experience, but this is so funny.

  102. Megan says...

    Oh my goodness, with plenty of bad dates under my belt, I have two dates that will never be forgotten. The first was with a guy I met when running. I had recently started running and this handsome man and I had ran past each other a couple times when he finally stopped me, chatted and ended up securing a date. I mean, kismet!! It all was going good until he revealed his entire (ENTIRE) past sexual history to me…starting with stealing money from the ice cream shop he worked at so he could go get blow jobs as a teenager from professionals. He proceeded to explain how now he no longer ejaculates because it “shaves 3 minutes off his life every time he does”. I never felt unsafe, so I had to see the date out, pretty sure my jaw was on the floor for most of it! It was totally bizarre and I never answered his call again. The second date story I tell all the time is how I went out with a guy and we ended up at a tattoo parlor. My date, let’s call him Bob, had his very best friend, let’s call him Tony, join. Fine by me, as he wasn’t a keeper either. I then proceeded to witness Tony get a tattoo of Bob’s (my date) face on the palm of his hand. NO LIE. I still have the picture and often pull it out for the evidence of said date. Any time I tell the story of these dates I still laugh so hard I cry!

    • Julie says...

      Wow!!!

    • Erin G. says...

      Here for the comments and, Megan, this was the very first one I read and I am laughing my a*s off!

    • Dee says...

      OMG! Both dates are hilarious and terrifying.

  103. Jordan says...

    I was meeting a guy I talked to on Tinder at Starbucks. He was 30 minutes late. I’m not sure why I even stuck around waiting that long. He said he’s always late… Anyways, he came up to me looking vaguely like his photos but in all black dirty t-shirt and sweatpants with dandruff/dirt/whatever all over his clothes and he smelled really bad. He then shook my hand and it was the worst limp handshake I’ve ever had. I casually mentioned he looks different than the guy in his photos that dressed in normal clean business/casual clothes and he says “oh yea, I use my brother’s pics so girls will go out with me…. girls are superficial like that and I like to prove to them it’s not all about looks.” Between the lateness, the handshake, the clothes, the use of someone else’s photos and the snide remark about women, I was so put off. Dude, you’re not starting off on the right foot by lying about who you are! Mentally I was done but I politely chatted for about 15 minutes and then faked an emergency on my phone with a friend to get out of there (which is the first and last time I’ve ever done that).

    • Maclean Nash says...

      Limp handshake = major red flag, always.

    • Roxana says...

      YUCK. What. a. loser.
      Completely agree about a limp handshake. Hate it!

    • rachel says...

      ew NO, THIS IS SO BAD. LOL

  104. Jasmine says...

    I went on a dating app date with a guy and afterwards, I felt pretty indifferent about it but didn’t have the heart to tell him yet. A couple nights later, I was giving my girlfriends the scoop on him and showing our texts and while I was talking about how I felt so-so about him, I looked down and realized I had accidentally RECORDED myself saying everything and SENT the voice memo to him! Needless to say, I felt like an awful human being — Apple, if you’re listening, please consider moving the record button in iMessage.

    • Meghan says...

      Noooo. I have second hand cringe for you! So sorry that happened! :(

  105. gaia says...

    Oh noo! How awful.

    I had gone out with this guy a couple times. He seemed nice but wanted something way more serious than I was up for, which I told him at dinner. It seemed to go over well. No hurt feelings. Cut to us going our separate ways when I realized I had left my keys in the park down the street. Cut to me scrambling around in the grass when, standing over me, he says, “You’re such a jerk.”
    Me not looking up, assuming he’s referring to the situation at hand, “Oh I know! How could I have done this?”
    “No, I mean, YOU are a jerk.”
    I blink several times and come up with no response.
    Cut to him standing over me, explaining how awful I am, while I continue to paw the grass.
    I did find my keys 20 minutes later (!!) and endured the chilly duo walk he insisted on to the subway (my place was in the same direction) only by reassuring myself that this would make an amazing story someday.

    I still can’t believe the nerve of that guy.

  106. Sarah says...

    Went on a date with a guy. Each had a beer. When the bill came, we decided to split, I put $20 down, he grabbed the $20 and said “I’ll throw it on my card”. My beer was $6 and the bill was about $14 with tax. Gave him a second a shot because maybe he wasn’t thinking it through and it’s only $14. Went to a cafe, I ordered a drink. He asked if he could try some and ended up guzzling half of it. Nope, this guy was just a clueless moron.

  107. BB says...

    I went to senior prom with the wrong “Greg” because he asked over the phone, and we were WAY too far into the conversation when I figured it out for me to politely back out.

    Also in high school, I saw Indecent Proposal – on a first date – when we were 14 and 15 – with a guy I knew from a church youth group. We walked out of the dark theater and just said, “BYE!” without making eye contact and went in opposite directions home.

  108. Toni says...

    I went on a first date with a guy I met online. He was smart, had a great job, and was very sweet during our phone conversation. We met in person at a wine bar by my work and grabbed seats right by the window.

    Things were off to a great start until he told me that in his spare time, he’s a clown. Not through an organization. Not as a volunteer. Just for fun.

    He showed me some pictures of himself in his clown outfit complete with the nose and the wig and the crazy outfit with the big shoes. And then he juggled at our candle-lit quiet table. He followed that up with a loud, and what felt like very long, cheer-like song that he stood up to perform. The bar got quiet as everyone stared. The waitstaff were laughing their heads off in the corner. People stopped on the street to look in the window of the bar and I prayed my colleagues were not among them. Our waiter came over to top off my wine glass and whispered in my ear “you need this.” And I did.

    • Megan says...

      Oh, I’m dying right now!!! Awful for you, but man, I can’t stop laughing!!!

    • Hanna says...

      Horrible experience -> GREAT story!

    • Justine says...

      God bless that waiter, lol.

    • agnes says...

      the waiter is a great character! you should date him ;-)

  109. Emily R says...

    I’ve been on a similar date. I thought it was someone else entirely, and the person it was, well – they were horrible. Talked over me, told me I didn’t understand the world or politics. You get the drift. I couldn’t have gotten out of there faster. What killed me was he texted me a week later to tell me what a great time he had! I let him know I didn’t feel the same, but best of luck. He then proceeded to tell me how wrong I was.

  110. Tabitha H says...

    There was the time freshman year in college when a boy I knew from the theater department asked if I wanted to get ice cream after a Saturday rehearsal with a couple friends. I said yes (because we were friends and ICE CREAM) and briefly wondered why he only mentioned our friends who were dating, but decided that it was probably a big group of people from the theater department.

    Fast forward to me telling my friends about it, and my friend Mary said. “Oh, I know about that!” It turns out the WHOLE theater department had been trying to set us up FOR A MONTH totally unbeknownst to me.

    We went, and it was fine, and I was convinced he was just playing along with the others because I’d heard he liked someone else. And then the next day he asked me out again. I panicked and said I wasn’t planning on dating my freshman year.

    We stayed friends, and then sophomore year he asked again. I went on a couple dates with him, but didn’t feel that spark, so I told him I just wanted to be friends after that. To the disappointment of the whole theater department and half of my hallmates! XD

    • Erin says...

      Once, when I was in college, I was getting a ride to a concert with my best friend, her then-boyfriend, her other friend Caitlin, and the boyfriend’s friend, Paul. Prior to the trip, my best friend instructed me that “everyone” was trying to engineer a relationship between Caitlin and Paul, who, various overlapping circles of gossipy people had discovered, had secret crushes on each other.

      So my best friend, her boyfriend and I smashed ourselves into the back of Caitlin’s VW Rabbit and eavesdropped on what was, more or less, Caitlin’s first date with Paul — she drove, he sat in the front passenger seat. They liked each other, you guys! The three of us in the back kept shooting sidelong glances that meant “THIS IS GOING SO WELL!” and Caitlin and Paul did end up dating for real after that. :)

  111. foundryandforge says...

    I went on a first date with a guy. Fast forward 2 years later, he’s moved in with me and I guess we’re a stable duo now. Awkard in that I blinked and here we are…

    • lex says...

      haha sweet! strangely agreed. I didn’t date a whole lot in my early 20s— I was the girl who was really hyper-focused on school (then starting my career after graduating) and mostly hung out with family, friends, or myself. To be honest dating made me very anxious bc I knew I couldn’t do it casually and didn’t feel emotionally or mentally prepared for any dating disappointments.

      Then a few months into my first job (Working at a university office) I met a graduate student who was also teaching courses. I had to speak to him regarding a work project I was assigned to. He asked me out a few days later when we ran into each other on campus and fast forward two years later to now, we are newlyweds.

      It all happened in the blink of an eye! Along the way it felt overwhelming, awkward, daunting at times but mostly just natural, comfortable, special, meant to be…I am very happy it happened this way.

    • Katie says...

      I remember looking at my first boyfriend and thinking “Who are you and how did you get here?”

  112. Christy says...

    I once went on a blind date with a guy who seemed great on paper – good-looking, helicopter pilot, etc. – but during dinner drank waaay too much and took great pleasure in telling me about how the pitcher for the girls’ softball team that he coaches (remember, this is a 12-year-old girl) is so talented, so beautiful, long legs, soft hair, a real “looker” (leer, leer) and actually pulled out a photo of her to show me. I sat in stunned silence and shock until he finally told me, “yeah, she’s my daughter, ha ha…” This is the same guy who when I got up to leave said, “what, you won’t let me walk you to your car? It’s not like I’m going to rape you, or anything.” I haven’t dated since.

    • Joanna Goddard says...

      OMG!!! appalling!

    • Julie says...

      He sounds presidential!

    • Emma says...

      Was his last name Trump??

    • Y says...

      Did his last name rhyme with Frump?

  113. H says...

    Oh boy I LOVE bad date stories. And I have many. The stories are at least what makes them worth it, and bonds you with other frustrated single ladies.

    After a lackluster drinks date in which I ended up paying for our drinks, and I politely excused myself out of the bar not wanting him to walk me to my car (hint hint, dude) I get a text that read: “If I had walked you to your car would you have kissed me? Are you a first date kisser?” Sigh and UGH.

    I went to my neighborhood bar for a nightcap and ended up with the bartender’s number instead ;)

  114. Annie says...

    I was once set up by a friend with a guy.. we text some before going out and he asked if I wanted to get ice cream. I’m a total weirdo and don’t like ice cream at all, but told him I could definitely find something there I could have even if it was just a soda. So we get there and he insists that I’m wrong about ice cream and orders me some even though I protested. Then he acted rude when I didn’t eat it all because I. don’t. like. ice cream! Then he had me pay for it.. I’m so glad I’m engaged and DONE dating!

    • Kim says...

      OMG what a dope!

  115. Julia says...

    I was 15. My dancing class was over and we all went to a ball. I shared a wonderful slow dance with a 14 year old boy I had not ever seen before. It was sooo romantic and physically intense! Although we had hardly talked to each other, we arranged to go to the movies a few days later. I started to panic on the very day, so I begged my best friend to save me. So she was supposed to accidentally watch the same movie (haha). “Oh, hi Julia! What a coincidence!” And she sat right beside me. The guy next to me, my best friend on the other side, I still felt so uncomfortable with this intimate movie-situation, that during the whole movie, I I hid my hands under my jacket in fear he might want to hold hands… There was no second date :-) – but the memory of being a young girl feeling overwhelmed with the whole love-relationship-thing that was soon to come given my age, is still valuable to me.

  116. witloof says...

    Survivor of some really really really awkward blind dates here. Once I was fixed up with a Jewish guy named, of all unlikely things, Adolph. He proudly told me that he lived with five Staffordshire Terriers and his mother {make that six Staffordshire Terriers? and by the way dude, I know perfectly well that’s a polite way of saying pit bull, you’re fooling exactly nobody with that}. After dinner, during which he disparaged my profession and rolled his eyes at my leisure interests, the waiter took our dessert order and then came back with Adolph’s to saying that the kitchen was out of what I had asked for. So Adolph ate his, while I watched.
    Then twice in a row I got fixed up with men who told me aaaaaaaall about their failed marriages and relationships on the first {and only} date, including a fist fight with a new wife’s ex husband who stalked them on their honeymoon.
    One guy whom I met in a random way and who seemed seriously promising {tall, handsome, smart, employed, charming} asked me out for a drink and then after a glass of wine {he mocked my French accent, acquired by living for a year in Paris, when I asked for a Cote du Rhone} told me that his wife of 29 years had died five weeks earlier. RED FLAG ALERT!!!!!

    • celeste says...

      “Fixed up”? Wow.

    • Alanna says...

      Pit bull isn’t a real breed it’s an umbrella term for various blocky head breeds including 1) American pit bull terrier; 2) American staffordshire terrier; 3) staffordshire bull terriers (aka English staffies); and 4) mixes of these breeds. American bulldogs often get lumped into this umbrella term too, as do some mastiff breeds.

    • Char says...

      I just want to say that I own two “pit bulls” (mixes of a variety of breeds, like Alanna said) and they’re great dogs! Super loyal and loving with big personalities. My boyfriend says that they wear their hearts on their sleeves and it’s so true! I just want to say this because I worry that comments like Witloof’s make people who may have no experience around “pit bulls” needlessly apprehensive of an entire group of dogs (and people that own them!) when they don’t need to be.

  117. Sam says...

    This is going to be a fantastic comments section (and it was a great story, Caroline). My contribution is having to hide in the bathroom so my date would actually eat his dinner. He never stopped talking long enough to take a bite or even ask me a question. Instead he went on and on about himself and his family’s dramatic grudge stories.

    To those out there still in the dating pool– good luck and God bless. Routing for you to find someone kind.

    • Deana says...

      Ha – I was out with a motor mouth once and could hardly get a word in edgewise. When I did get to talk and said, “And then I was abducted by aliens”, he just nodded and continued to blab!

    • Roxana says...

      Deana, LOL! ” And then I was abducted by aliens.” That is awesome.

    • rachel says...

      right?! I am ALWAYS so grateful I dont have to date anyone but my husband! Dating is so awful.

  118. Ellie says...

    Maybe 5 years ago in my early stages of online dating: We meet at a bar and right off the bat he immediately starts talking about himself (to the point where I can’t even get a word in). Says he’s surprised I didn’t ask what he did for work before we went out because he’s unemployed “and that’s a deal breaker for most people.”
    Some highlights: Offered to buy me a drink and then complained about how expensive it was ($7), told me multiple stories about how his cat was the most important creature in his life, but the real kicker: pulled out his GAMEBOY and showed me a video of him making meatloaf. He was maybe in his early thirties.

    Thought seriously about making a bathroom exit and leaving entirely, but instead I explained that I didn’t want to go out with him again and left him at the bar.

    • Faith says...

      A video of him making MEATLOAF? I am dying.

  119. Maggie says...

    I am the world’s biggest extrovert – my dating profile was “I can talk to a wall but I’d rather talk to you”. And yet… I went on a date with someone so boring that the waiter kept sitting down at our table to chat. He could tell that we had *nothing* to talk about haha. The waiter got a great tip! The man did not get a second date.

  120. Sarah says...

    Went on second date with a guy who wanted to follow dinner up with a soak in his hot tub. It was January in Iowa. I hadn’t shaved in quite awhile so it was a definite no. He seemed to think I was just being shy about putting on a swimsuit. I have to plan ahead for a bathing suit situation.

  121. Roberta says...

    The entire time we were at dinner, he talked about his hemorrhoid surgery. First date was the last date.

  122. Jacki says...

    I went out with a guy I met on Plenty of Fish who in the first 10 minutes made a homophobic joke and an anti-feminist joke (my profile stated I was bi and that I was a Women’s Studies instructor). Then he proceeded to tell me that he was missing his front teeth (smiled with his mouth closed on all his profile pics) because he wasn’t very good about personal hygiene. That was the last date with him.

    • Alli says...

      Oh my god! This one.

  123. Agnes says...

    Ohhhh. I have sooo many. So many. Maybe not that many. But too many for me. Here’s one – the guy who was 14 years younger, who convinced me that he was ‘mature for his age.’ I wanted to prove to my friends that I am not as picky as they say, so I went. On the date, he got lost meeting me and when the bill came said ‘what do we do now?’ I said, ‘split the bill.’ If ever there was a friend situation, that was it. Then we went to the park and he asked me to be his girlfriend. I said no, as I was too old for him, but he then texted me for months, pretty much just saying, ‘hey babe.’ Sigh. I guess it could be worse. Another one, he insisted that he paid and ‘order anything you want!!’ OK. I got the soup. He didn’t order anything, and asked for some of my soup. I said no. Because if you could only afford one soup, I would be happy to pay for myself! And another guy, told me how much he liked my dress, and then said, ‘if my assistant (age 27, younger than me) came in here, all the heads would turn!’ Just.. no. Already putting me down?? No! No more dates for YOU! (He did ask and I said no.) I have had some good dates too, by the way. Haha! Can’t wait to real the comments on this!! Haha!!

  124. Erin says...

    After telling a fellow grad student that I thought her friend what’s-his-name was cute, she set us up for a dinner date. Dude was friendly enough, but spent what seemed like a very large portion of the date telling me he “didn’t believe in science” … oblivious, apparently, to the fact that our mutual friend and I were both earning graduate degrees in a biological science. Before this date, I’d thought having “deal breakers” was kinda petty, a matter of not giving a nice person a proper chance, but I remember this lightning-bolt moment of realizing “WOW, this is a deal breaker.”

    Also, what in the world did he think science WAS? I didn’t feel brave enough to ask a confrontational question of someone with whom I did not intend to have a second date, so I never found out!

  125. Laura says...

    My most awkward date was also my first date, when I was 15. There was a not very attractive boy roughly my age who went to my church, and he somehow got my number and called to ask me out to a movie. My parents insisted I go, since he was a nice church-going boy, so I agreed to see School of Rock with him… even though I had already seen it with my friends! I wore an unflattering turtleneck and he wore socks with sandals. I laughed too early at some of the funny parts of the movie since I knew they were coming. I desperately wanted to go home afterwards but he suggested we get milkshakes and drink them in his car in absolute silence. We did not have a second date.

  126. Amy says...

    Oh my goodness!! That is awful!! 😂

  127. Amanda says...

    I had a first date take our $25 bill from our waitress only to tell me (after the waitress walked away) that because I ate 2/3 of the pizza, I should pay 2/3 of the bill.
    I paid the entire bill, and assured him I had his number, but that was our last date.

  128. Ruth says...

    I once went on a date with a guy from match.com who ordered a bottle of wine, proceeded to drink the entire thing himself, talked about how he was raised in a cult and had spend the past few years doing copious amounts of MDMA, asked me if I had any cigarettes (I did not), and then asked me to drive him home when dinner was over (I did not). He texted a few days later to go out again (I did not).

    Ah, dating.

  129. Rachel says...

    I was just telling a friend this story yesterday:
    In college I ran into a guy I vaguely knew from high school. He asked me to go to dinner and then to his intramural football game (first red flag). I agreed, but the game ended up being rained out at the last minute. Instead of finding a logical date alternative, he asked me to hangout at his friends’ apartment.
    When I was coming back from the bathroom, he hid around the corner and actually tackled me to the ground in an attempted “tickle fight” as if I were his toddler child. I just went limp and asked him to take me back to my dorm. He had the nerve to ask if he could come up (spoiler: definitely not).
    Then a couple years later, we ended up being servers together at the same restaurant- so awkward.
    My husband still teases me ab the “guy who tackled you”.

  130. Heather says...

    HAH! So many lols at this one

    First, I wanna know more about Silly Hat Evan, he sounds great.

    Second, isn’t it great that we all I *THINK* seem to be working away from having to give our numbers out begrudgingly? I know I’m getting better at saying no.

    Third, so many bad dates. One guy in particular talked about having to drive a lot for work, so I asked him what he liked to listen to in the car – figured that was a safe segue into music! podcasts! audiobooks! Nope. He said aggressively “I listen to talk radio, yea that’s right, I listen to Rush Limbaugh, YOU GOT A PROBLEM WITH THAT?”

    I don’t even share this as a political issue, but just a ugh dude TOO MUCH issue.

  131. Lucia says...

    This isn’t a date story but I had an accidental hire. We had interviewed but I hadn’t started calling with offers when one of the people we interviewed came in to complain about the interview. It was for an entry level position and they felt some of the questions had required previous experience. I disagreed because they were questions that could be answered with just basic life experience, time management, how to answer questions when you don’t know the answer, etc.
    This person had been on my list to offer a job but I decided they seemed like a nightmare after this unpleasant exchange and I gave the job to someone else. When that person came in to do their hiring paperwork, it was them! I had mixed up the names and hired the wrong person.
    I felt like such an idiot but I was right, the person was a pain in the ass, argumentative and needy. Luckily, They moved on fairly quickly so I was able to hire the other person.

  132. Taylor says...

    My now fiance, Richard (hi Richard love you!) and I met after some stops and starts of conversation on a dating website–I had no intention of reaching out to meet except that he had listed Japanese Breakfast as a band he liked on his profile and knowing he was new to the city, I asked him if he was going to her concert the next night and he was!

    I DID have a first date scheduled with a different guy for the night after the concert. Well, of course, it was love at first sight with my now fiance, we spent the entire night talking, kissing, laughing, it was truly the most instant chemistry I’d ever felt. And I had a date with someone else the next night!

    It’s incredibly strange to think about it now, but I told my now-fiance about the date the next night (he was going to be out of town for a few days) and how I was now dreading it! But felt like I had to go! So I did! And of course, it was NOT GOOD. I kept thinking about the night before and itching to text Richard and I pretty much ended up telling the guy, “listen, this sounds crazy, but I met someone else and felt like it would have been rude to cancel the date, but you’re cool and I’d love to be friends.” (We never spoke again, womp womp.)

    Anyways, got home from the date, texted Richard who I had known LESS THAN 24 HOURS “date was a bust.” And he responded, “I’m grateful that I am a couple hundred miles away from you-you can’t see me clicking my feels mid-air. He doesn’t know what he’s missing.”

    Sometimes bad dates are a sign of something really, really good.

  133. Julie S says...

    LOL. OMG. I’m not dating anymore but definitely going to start using last names too… for all future possible awkward situations.

    One time a guy had a similar friend asked me out a few times, after awhile I finally agreed. I knew his family and he was a nice guy but I’m still not sure why I said yes. Anyway- He picked me up, said Hi. Then never spoke again the entire date. He ordered tickets to a movie for us and sat two seats away from me in the theatre. Then dropped me off hours later and never spoke a word the ENTIRE time. If I asked a question he just nodded. I don’t know how it was possible but it was. And holy cow was it awkward.

    • ANDREA says...

      OMG! Reminds me of a blind date I went on at a coffee shop. At the 45 minute mark, out of nowhere, the guy stands up and said that he had to go. I told him that I was going to stay and he walked out.

      I think he must have been trying to talk to new people or was assigned to do something in therapy.

  134. Deana says...

    Ha! Good post. I have several, but the worst was a blind date who suddenly pulled off the road (I thought he’d lost control of the car) to take a leak – right in front of the vehicle headlights, not even going behind a bush. We were on our way to a party that, I found out too late, we were actually crashing. The cops then broke up that party because my date parked on the lawn, refused to move the car, and cops were called. Luckily, I lived nearby and walked home, but he followed me there. Oh, and he later became my next door neighbor, but was actually a decent neighbor, much better than a date!

  135. Oriana says...

    I went on a date with a guy who insisted on ordering appetizers even after telling him that I wasn’t hungry or interested (it was a 9PM casual drinks date) I didn’t eat any of them other than a couple bites to be polite. The bill came and he said, “do you want to just split it?” ummmm, what?! Then he walked me to my car and tried to kiss me. I backed up and he stepped forward. And then again until I was pressed against my car. I finally ducked into my seat and pulled the door shut.

  136. RACHEL says...

    CAROLINE. Your writing/stories are THE BEST. That is all.

  137. Kate says...

    My date and I rented a movie from Blockbuster. We thought we’d gotten Scream 2 but when we got to his apartment Evita was inside. Uhhh, no thanks. We wound up eating Taco Bell and watching TLC’s A Wedding Story. Never saw him again.

  138. Allyson says...

    I went on a Tinder date with an aspiring pro-wrestler calling himself “Crossfit Man.” He had looooong hair with a very much receded hairline. He ordered an app, entree & dessert (I had an entree & water) and at the end he asked the waitress to split the bill 50/50. He also talked about just getting fired from his job at a hospital for HIPAA violations. I couldn’t get out of there fast enough. Drinks dates > dinner dates.

    Somehow, I legit met my future husband on Tinder shortly after.

  139. I went on a date with a man named Kevyn, who I was unhappy to learn shared the same qualities as myself! It’s nice to meet a similar soul, except when they mimic all of the worst parts of yourself. When the night became unbearable, I faked a phone call from my friend and pretended that she was having an anxiety attack and excused myself to “take care of her.” I fled after that.

  140. Lisa says...

    A guy once suggested that we make out “like weasels”. That relationship didn’t last to the second date.

    Then, I still kind of feel guilty about this, and in my defence I was young and stupid. I met this guy at a party who was nice enough but I wasn’t really attracted to. He asked me out for dinner and I thought “why not, free meal” so agreed. Between that and the date, a friend and I started kind of dating. Queue date night with this guy – it’s ok ish, not super exciting and at the end of the night he says “do you want to have lunch tomorrow?” And I said “oh no, I’m having lunch with my boyfriend. Maybe some other time”. He looked crushed. I then spent then next two years of university avoiding him, and recently someone who kind of looked like him, and panicked

    • Breamons says...

      I really want to know what… “like weasels” MEANS???

  141. Heather says...

    Not exactly a date but still date-related awkwardness … I once went on a date with a boy and it was fun but the vibe was more friendly rather than romantic. I never thought much about it when he didn’t call or text again (I didn’t call or text him either). Ran into him at a party a few months later and he looked at me panicked and said “I’m so sorry I never called you. I had ebola.” Stunned, all I could think to say was “Oh my, I’m so glad you recovered.”

    • Rosie says...

      I’m stealing that if I am ever single again!

    • Silvina says...

      “I had ebola” LOL!!

  142. Cindy says...

    ugh. first date after signed up for match and the somewhat older-than-me man reprimanded me for having pierced ears and tattoos (I only had 3 tiny ones at the time). Compared me to his daughter as well. No second date for him!
    Love your solution, Caroline! I did the same thing when i was dating…one guy was originally from Nashville so he became ‘Nash’; another belonged to a prestigious country club so he became ‘Country Club Guy’; the one that was 11 years younger than me became ’35’. Way easier to know who was calling…and if i wanted to answer :)

  143. celeste says...

    Photos of his apartment, what?

    My high school sweetheart dumped me on my porch and gave me several copies of his senior picture right after my mom was diagnosed with cancer. I tore them up and threw them in the closet with everything he’d given me and didn’t date for two years, LOL. We still don’t speak.

  144. Jaclyn says...

    Oh! I can’t wait to read everyone’s stories. My most awkward (first) date happened recently and can be summed up by two lines of conversation. Me: I have to go to the bathroom. Him: Number one or number two? ACK! After clarifying that, um, it was number one, I basically high-tailed it out of there. (Also earlier in the date, about three minutes into meeting, we were walking to the beach with smoothies, and he pointed to a random guy on a bench and said, “That’s the sixth guy that’s checked out your boobs!” So yeah, that should have been my signal to flee.)

  145. Dora says...

    I once went on a date with a guy who, in hindsight, was a complete jerk. He suggested we drive to the beach (I drove, in my car) for a fun afternoon beach day. He then proceeded to go on a jog on the boardwalk for an hour and a half (!!), came back to where I was waiting on the beach and suggested we drive back to his apartment. It was only our third time hanging out so I didn’t have the courage to call him out for completely ignoring me on our “date”. Never saw him again but he did text me to ask him if he had left his jogging sweatband in my car.

  146. gracekelly812 says...

    Has to be the date where the guy showed me a lump on his shoulder, told me it was the twin he absorbed while in the womb. He knew because they found a tooth during an unrelated scan when he was younger.

    He then proceeded to tell me, in detail, about the bender he’d gone on after inheriting some money from a distant relative. The conversation sort of floundered after that.

    • Anna says...

      “The conversation sort of floundered after that.”

      Dying.

    • Allison says...

      A real life My Big Fat Greek Wedding moment!! 😳

    • freya says...

      i want to know more about the twin!

  147. Hannah says...

    In college, I went on a date with a roommate of a friend of a friend. We were going to a casual diner just off campus, very lowkey. On the way into the diner, he grabbed a newspaper off of the stand in the entry. Fine, he likes to stay up to date. Good, even.

    He then proceeded to READ THE NEWSPAPER TO ME throughout our dinner.

    We did not go out again.

  148. Mouse says...

    I went on a date with someone I wasn’t really interested in but felt like I should. (Ah, I was young and it was loooong ago…..) We went in his car, parked in a parking structure and walked down the stairwell. Heard the door click behind us in an ominous way, and it was locked. At the bottom, it was also locked; we were locked in the stairwell. We had to pound on the door and yell to passersby to eventually get out. Needless to say, it was not a good date, and I think we were both relieved when we didn’t attempt another one…….

    • Kate the Great says...

      Oh, my. How awkward.

  149. In college I went on a date with a guy who took me to a house party in our apartment complex. Imagine my surprise when, before we sat down on the couch, he took out a GUN from a holster (is that even the right word?) hidden under his shirt and placed it right on the coffee table. I tried to play it cool but my bright red face and profuse amount of sweating probably gave me away. I told him to put the gun away and that I wanted to go home. He insisted on walking me to my door, so he (and the gun) accompanied me on my walk. I did not go on a second date with him!