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. Cindy says...

    I gave up dating, way too many crazies.

  2. ErinM says...

    This is the sweetest story! What a good man you got <3

  3. Holly says...

    This wasn’t necessarily a bad first date just one with an awkward ending!

    A guy who had been interested in me for months finally asked me out for drinks and to a movie (very bad for a first date but I ran with it). The whole date was amazing, from starting out with cocktails to being tipsy and giggling in the movie theater. At the end of the date I offered to drive him home. He ubered from his house and I drove from work. As we were parked in front of his house saying our goodbyes he was going in for what I thought was a hug which then turned out to be an awkward kiss / make out sesh that still has me laughing till this day. He immediately jumped out of the car afterwards and ran inside of his place. This guy ended up becoming my now long term boyfriend who I love dearly but we still till this day argue who went in for that first kiss. *and it was definitely him-LOL.

  4. Molly says...

    I got asked out in a doctor’s office…while I was with my mom! He had a big smile and was a very smooth talker. The big red flag should have been that he worked in a women’s shoe department. We went out a few days later, he picked me up (was late) and we proceeded to the fancy Mexican restaurant in the nearby beach town.

    Little did he know that my sister and her friend decided this guy sounds like a creep and booked a table (with my consent) at the same restaurant. We sat down RIGHT NEXT to them.

    The date went on…and on. He was very nauseating and wouldn’t stop talking about his high school football career. I get a text halfway through and it was my sister saying “meet us in the bathroom”. I excused myself and met them – they said I looked incredibly miserable – which I was. We decided I should end the date earlier than later and NOT feel bad for doing so.

    I took their advice and after dinner said “I was busy the rest of the summer so no I cannot go out with you again”. He laughed. I never saw him again.

    To this day I’m so thankful for my sister and her protective and hilarious intervention. She has since passed away and I will always treasure that date for what it was and what it wasn’t. Thank God for sisters!!!

  5. Silvina says...

    Probably the best comment (and story).

  6. Leah says...

    A couple of years back I was hopelessly swiping left and right on Tinder. I ended up matching with this law student named Dave. He was so attractive, like almost too attractive. Our banter was witty and entertaining, so of course I said yes to a date. We go to get apps, some drinks, a follow-up beer on my roof. We kiss, it’s like sparks fly kind of stuff. Then he gets serious and tells me he has a long distance girlfriend and also Herpes… I thanked him for his honesty but assured him I wasn’t a side-chick kinda gal and that this changed things. Sent him home and on his way, no goodbye kiss. Cut to two weeks later, I’m at work, an ad agency in NYC. The mail guy brings me an envelope. It’s a drawing of me, my exact profile and arm tattoos etc, with a 5 page letter…. From Dave. Apparently I was the love of his life, his words. He then got a job at the coffee shop across from my house. And that was how I got my first stalker…. The end!

    • tod says...

      OMG! That´s scary. I hope he lost his job and moved away.

  7. Katie Rose Taulbee says...

    A few years ago when my crush asked me out (to a midnight movie showing) I was so excited I said yes immediately. Unfortunately, my excitement had caused me to forget that my ex was in town for a job interview and had asked to stay with me for the weekend. Without thinking I blurted out “can Dave come too”? (I’ve never been smooth). My crush magnanimously agreed but then panicked and invited his ex to come along as well. Fast forward to midnight as all four of us walk awkwardly into the theater and fumbled to chose our seats. I remember nothing of the movie and my palms still sweat when I think about that night, but my crush and I did a re-do date later that year and now that we’re married our “first date” story is one we tell with mutual glee and embarrassment.

  8. Laura says...

    met a cutie who was working as a Genius in the Apple store (I dig nerds). We hit it off based on music and decided to grab dinner the next night. I agreed to meet him at his place which was right down the street, then we could ride together to the restaurant. I was a bit put off by an aggressive smell that seemed to be seeping out from his apartment door when I walked up…
    Only when he opened the door and invited me in did I realize that the smell was coming from the *7* ferrets who were running wild in his home. The carpet was covered in their excrement and I had to stifle a scream as they all tried to climb up my legs. I am animal lover and all, but. No. Nooooo.

  9. Sarah says...

    After dating my boyfriend (now husband) for a while long distance in college, we went out to a favorite local pizza spot with my parents, so he could meet them. As we waited for a table, there was a drunk (or on something) couple majorly making out with each other nearby in the takeout waiting area. We kind of laughed/ rolled eyes/ wrinkled noses. Then to my horror, moments later, I heard an oddly familiar voice say my name, then my first AND last name louder questioningly, “It’s me, Tyler ____!” The guy making out had been my sophomore year HS boyfriend, whom my parents had never met, but heard plenty about at the time, and whom I hadn’t seen in 5 years. So, my parents and boyfriend both had the pleasure of meeting my very inebriated ex and his date that night.

  10. Heather says...

    There are so many comments on here mine may not be read but in case you are still reading I have to share about a guy I sort-of dated after college. He was very wealthy and also very cheap never once paying for dinner – I think he was afraid girls wouldn’t want to date him and only wanted his wealth so he made that a non-starter. The real truth is that he was SO boring; on date one I had told him a funny story about myself by date 5 he was telling me that story back to me pretending it was his! So long sucker!

  11. Sarah says...

    On a first date a guy asked me to work out how many times I’d had sex. Not how many people I’d slept with, how many actual times I’d had sex. I’m so polite I tried to do the math. Then when I got home (by myself) I realised he’d been sending me snap chats of himself the whole date trying to get me to kiss him. Yuck.

  12. Ashley says...

    In college, a guy from one of my classes asked if I wanted to grab a sandwich at one of the places across from campus after class, chat about the article we had due. I said sure, we went, it was fine. Halfway through, he pulls out a pack of cigarettes and starts hitting it against his palm. Before I could think about how rude this sounds, I blurt, “if you light that up, I’m out of here.” He freezes and kind of laughs, but when I don’t, he asks, “wait, are you serious?” I nod and tell him that I’m really against smoking and I’d rather he not do it around me. Immediately he gets angry and says, “you’d really end our date over me smoking?”
    HOLD UP. Date?? Since when was this a DATE?!
    I think my face immediately reflected that thought, because I could see it dawn on his face that I didn’t know it was a date.
    So yeah. I think we lasted maybe 5 more minutes after that before we “had a class to get to.” That was definitely awkward. For years I’ve felt bad about how rude I was about the smoking, but I also hold strong that yes, i would end a date if he refused to at least go smoke away from me.
    Funnily enough, I’m still friends with the guy, though we’ve never acknowledged that day since.

  13. Kiley says...

    I went on a date with a friend’s roommate, and he seemed really nice when I had met him prior. On the date he was like a completely different person. He talked incessantly about himself, and was annoyed that I stopped to pet a dog when he had a 15 minute long conversation with the beer delivery guy at the bar where we were having a drink. I also had the audacity to check my phone when he went to the bathroom (didn’t take it out when he was around mind you) and he threw a coaster at me from afar and told me to put it away. I was willing to chalk this up to first date jitters and him trying too hard to look impressive, but he came home and told my friend that it was the “worst date he had ever been on.” Yeah, okay.

  14. Kay says...

    A few years ago, I accepted a date from a man my friend had set me up with. He picked me up and on our way to eat he played Celine Dion power ballads the entire ride. After eating, we went to go see a movie. an Indian movie. which was about 4 HOURS LONG. He kept trying to put my head on his shoulder and the scent of bare scalp (he was bald) kept making me want to gag. I kept excusing myself to go to the bathroom. The entire date he kept asking me if I was his boo (“You’re my boo right?”) On our way back to my house (he was going to drop me off and definitely NOT get invited in) he began to complain about how he would get blue balls and if I could just touch his little man to help him out medically. Ok, our date was officially over now. I told him to drop me off at some random gas station, when he asked if I would like to meet his parents now because he was sure I was the girl he was going to marry. I said no and walked the entire way home. The next day I received a text from him saying I need to lose a few pounds from my stomach because otherwise how would we perform all the sex positions he had in mind. Block. Coincidentally, I am no longer friends with the girl who set me up with this walking disaster.

    • Julia says...

      What a nightmare.

    • Dee says...

      Disgusting.

    • Annie Knapp says...

      Lots of good stories here, but you win, my dear! Incredible!

  15. Rashmi says...

    Much as I laughed at a lot of these, I have to admit that quite a few ‘trends’ I could observe here leave me a little uncomfortable.
    1- most stories state that women are expecting the guys to pay for the date, so much so that a lot of stories mention splitting the bill as an off putting thing (!) Really?????
    2- Even more worrisome, several stories mention something like “I wasn’t that interested but thought let’s go ahead and get a free meal/drink”. That’s beyond ridiculous to me. It’s actually the argument you would find on a lot of anti-women/Incel type forums but the ladies on here are more than confirming this.
    3-Too many stories have women feeling uncomfortable and yet continuing the date, leading the guy to then act surprised when they refuse a 2nd date. Why on earth would you go to a second bar or extend drinks to dinner if you are having a bad time??

    • C. says...

      +1

    • Jessica O. says...

      for #3, this isn’t women taking advantage of a guy or trying to mislead him. I find it is usually one of two things: 1) they do not know how to politely extract themselves and feel an obligation to see the date through, “be a good sport,” “give him a chance,” or 2) they are legitimately scared of his reaction either from signals he’s been giving off or that they just have gotten from men over the years who snapped with anger when rejected. most women I know can recount a man going from “can I buy you a drink” to literally cussing at your face (“I would never date a fat pig like you anyways!”) upon a polite rejection.

    • Nicole says...

      In defense of a lot of these stories, they probably didn’t happen yesterday. When you’re younger and female, you have what you see around you which is a patriarchal society. Once a lot of women start realizing they can say ‘Nope!’ on it, they do. I feel like this comment either wants to desperately understand why you would not know your worth as a woman and you’re always enough or it’s just not able to empathize that this is exactly the problem because women are thought of as objects and treated like that. Our entire society teaches women that men can buy them so of course this is the theme throughout a lot of these.

    • Dana says...

      Seriously? Do you not understand the uncomfortable position women are in when confronted with a man they don’t like? Women are conditioned by society to be nice, as well as the ever present threat of male violence. Women usually slip away from a date they don’t like at the natural ending, or when they otherwise feel safe to do so. This isn’t because they’re looking for a free dinner!

    • Rashmi says...

      @Dana
      I totally get where you are coming from. I dont see why you feel the need to attack me when I asked some legitimately worrying questions I had on this series. Most of the stories being narrated are not about women feeling unsafe. It’s about them voluntarily putting themselves in a scenario and not getting out of it when they want to. Being conditioned by society is not really an excuse for educated liberal women behaving in this fashion. If the Failure to express yourself is coming from a lack of self worth, then instead of blaming the guy, the ladies in question really need to look inward. Because not speaking up or expressing your point of view is not just limited to a one night date, it will lead to bigger problems in life. I am left wondering if on a similar forum with a target audience made of males, the same stories would be narrated with a completely different viewpoint due to the sheer lack of vocalisation.
      Also, I really dont see how the argument of safety justifies women being upset when a guy doesn’t pay for a date.

    • alle says...

      I’ve definitely meditated on the anger many men so easily express when they are rejected, no matter how kindly. I feel like I need a man’s explanation of this surprisingly common reaction – which I would love to see here? It would be so helpful. I’ve had three of these reactions from men I would otherwise rate as entirely civilized. All were on the wealthier side so I understand it’s partly privileged white male entitlement but – anger?

      I don’t get it dudes, that is how courtship has always worked. Thank god things are changing!

    • Casey says...

      My go-to move in my dating years was to show up early, order and pay for my own drink (closing my tab). That way, if the date went south I could make a quick exit and the only thing either of us wasted was our time.

  16. These stories are amazing, hahaha. I love this post.

    A few years ago I was feeling extra inspired to find a relationship, and I was going out on a ton of dates via match.com. I set up a dinner date with a promising guy. I arrived at the restaurant first and decided to just go ahead and get a table.

    A couple of minutes after being seated, I looked up and I saw my date coming toward me. I got up and said “hello!” and gave him a big hug. I sat down and asked him how his weekend was going. He just stood there and said, “good!” with a smile on his face, and then intently asked me how I was doing.

    I remember giving an answer and thinking, “why isn’t this guy sitting down?”

    We chatted about something else for a minute or so and then I suddenly realized….. this guy is not sitting down because HE IS THE WAITER. He resembled my date, but he was NOT the guy. He was wearing a black tshirt and nice jeans; something a lot of guys wear on dates.

    Hahahahaha.

    I could tell quickly that the waiter was trying to place me. He clearly thought that we must know each other and was trying to figure out how.

    Anyway, I was so embarrassed, and just decided to play along like we knew each other. My date arrived a couple of minutes later (he got a hug too), and we ordered dinner. At the end of the dinner, the waiter dropped off the check and was like, “it was so good to see you again!”

    :-)

    • Jessica says...

      That’s amazing! Hahaha

    • Claudia says...

      I really shouldn’t read these posts during work time. I just laughed out loud at the “HE IS THE WAITER”. ahahah

    • Annie Knapp says...

      I just laughed out loud! Too funny!

  17. Sarah says...

    A guy I worked with set me up with his brother convincing me he was PERFECT for me and that we would get along great! I met the two at the dinner theatre and, to my shock, my date had a pimp hat on complete with a purple large feather. I was completely humiliated as we were being led to the table. What’s worse, the waitress had to ask him to take off his hat — which he did reluctantly. I prayed that I didn’t know anyone in the restaurant!!

  18. janee says...

    We were living in Tokyo, I was a model, he was an American journalist and we got a little lost while walking through a neighborhood at night (Tokyo has great neighborhoods). A hard summer rain suddenly drenched us so we frantically looked for a place we could wait it out and dashed into what looked like a decent bar. It turned out to be a fancy high-end “bar” of such immaculate low-key elegance that it took a minute to realize we were way, way out of place. We were soaking wet and there was an unspoken understanding of the exact situation by everyone as we quietly sat at the bar and each ordered one very very expensive drink. The cost blocked out all memories of what that drink was haha but I do remember they each came with their own screamingly chic amuse buche. I’ve never encountered anything like that place again and wish I’d taken a card or something to remember it by.

    • janee says...

      The awkward part was that we were on a first date and both on tiny budgets because Tokyo is expensive and he insisted on paying even though his eyes were bulging at the cost, because: first date. If I remember correctly it was somewhere in the $70 range total. This was in the 80’s and I had no idea $35 drinks were possible! I think I left the tip? Because I was young I was deeply troubled by whether or not he should be allowed to pay. I’ve since decided, after deep consideration, that I love chivalrous men, the ritual of gentlemanly behavior, and if they want to pay I let them and enjoy it.

  19. kelly says...

    Ummmm…. as a 28yr old when he picked me up for our date and I saw that the back of his car window was LINED with stuffed animals.

  20. witloof says...

    I got set up on a blind date by my boss, who thought I should meet her son’s good friend. He sounded kind of stilted and awkward on the phone, but I chalked it up to nerves. He told me he couldn’t go to a movie or to anything involving live music because he was in mourning for his father, so he suggested we take a walk in Central Park and tell each other jokes. I love hearing and telling jokes, so this felt promising. The evening before our Sunday morning date, he called me up to say that he had diarrhea and probably wouldn’t be able to make it. Yes, he used that word. The next morning he called two or three times to tell me more details about his diarrhea until I unplugged my phone and fled my apartment. When I got home later that evening there were three more updates on my voice mail.
    On Monday morning my boss rushed into my office to ask me how the date went. I replied, “We didn’t wind up meeting because Marvin had diarrhea.” She stared and me for a second, shrugged, and said, “And now we know why he’s still single.”

  21. Erin says...

    I’d like to start by saying that I am happily married and have been with my (amazing) husband for 12 years. In the Before Time, I casually dated a guy with ‘born to kill’ tattooed on his throat, who, after dating for a few months, invited me to a fancy dinner in the North End. Turns out he also invited another woman he was dating. He introduced us, we all sat down to eat. I was in a trance for the first half of the meal, until finally I shook myself awake, told him off, and left. I’d like to say I never saw him again but I found out a bit later that our relationship was immortalized on Google street view. Whenever someone looked at my apartment for the next seven years, there we were, standing on my porch.

    • alle says...

      omg – horrible! You can blur that out you know – it’s easy to do, maybe look into it!

  22. Anna says...

    After a breakup at 21, I reluctantly agreed to a date with a post-doc researcher from Russia at my university, who seemed at least 30. We went for a cocktail (White Russian for me!), which he ordered from the bar and paid for. We awkwardly discussed his research (pure mathematics) and I declined another cocktail. When I said I need to go now, he wanted to walk me home. Even though it was late, I let him walk me to my college instead (so that he wouldn’t know my address).

    Also: based on the comments, how many of us (especially at a young age) have agreed to go on dates reluctantly to “be nice”?

    • alle says...

      I feel so fortunate that as a young teen I learned how to say no graciously and immediately which gave me so much confidence. And I learned that – and other very helpful things – by reading Seventeen magazine! (no affiliation). I lived in a backwater then so that magazine saw me through my teen years.

      Therefore FYI to anyone with a tween girl in their lives: quality teen magazine subscriptions make a GREAT gift and are not frivolous – they are full of helpful info and are even when available online are still so much fun to receive as a hard copy in the mail every month!

  23. Taylor says...

    I often think to myself, will the first dates ever end? I met up with a guy from a dating app. We messaged for 10 days and he seemed totally normal. We went to a small plates restaurant where he ordered one small plate for us to split, the tiniest portion of meat. Who orders that on a first date? He proceeded to share his life story, from being raised in a cult, not knowing how to multiply until 15, to wishing he could quit his job and relax in a hammock while smoking weed all day. Told me he wanted to sell his car to use public transportation…we live in Texas, there is very little public transportation. Wanted to move to Peru, a country he had never visited. Did not even offer to pay for my drink at the bar after I had drove 45 minutes in the rain to the restaurant. The real kicker, he asked me to go to a sex store at the end of the date…I worry for the girl who thinks any of this is normal. I’m learning to be strong and leave when I know things aren’t going well. Dating is hard to navigate, I could really use a manual or a maybe margarita.

  24. AE says...

    1. Senior year of HS, I asked the guy I liked to prom [he said yes!] and then the guy who liked me, asked me to go with him. I was too nervous (?)/concerned w/ his feelings to say “no” outright and told him that I would think about it. I never got back to him but he showed up night of prom w/ a corsage. As did my actual date. So I ended up with 2 prom dates, sitting between them during the limo ride, etc. Super awkward. [also, I’m seeing a pattern here of women “being too nice” to just tell guys “no”– amazing how early that starts!]

    2. Slept over a guys house after a couple of dates and woke up… having PEED his bed [yes! as an adult! I had the pee dream and everything]. I was too embarrassed to say anything, so I got up, leaving him in it, cleaned myself up, and fell asleep again on the couch in his bedroom. He was NOT happy. But…we are getting married in 3 weeks so….#luckypee?

  25. AP says...

    My most awkward date started like a fairy tale. I was at a fancy Teen Magazine party in LA and he was the bass player in a semi-famous band they had hired to play. We made eyes at each other the entire night while he was on stage and when they were done playing he made a beeline right to me. We hung out for a short time with his “children of celeb” friends and made a date with me the following morning for brunch. I thought it was so dreamy that he had made a date for a ‘sober’ time, rather than get me to stay at the party all night. I had stars in my eyes when I showed up at the brunch but the actual date ended up being SO boring. The conversation flowed like molasses and at the end he actually TOOK A FEW OF THE DOLLARS I had left for my own tip (we went dutch….eye roll) “Gas money” he said. WOW. The dream is NEVER the reality, my friends.

  26. Casey says...

    Several years ago went on a first date for dinner with a guy I met thru a dating app. Dinner on a first date was not my usual MO, but he offered up a new Thai place I was dying to eat at. Fast forward to dinner…he tells me all about his grandmother’s lake house that he spends most of the summer at, uses her boat, invites friends up etc but makes sure to stop going when camp has to be closed up for the season bc he doesn’t want to help. Ugh. THEN when I mention studying abroad in Latin America and how it was amazing he goes on a racist tirade about Latinos (fail #2 for those keeping track). Lastly, the bill comes, it’s $90, he pays but only leaves a $10 tip. (Side note: I’m a waitress at the time). We awkward goodbye, I dodge the kiss & pretend to leave. I circle back to give the server a proper tip – the server just about died laughing when I gave him an additional $10 and apologized on my date’s behalf and explained it was a terrible first date.

    Different date, different guy, I was the awkward one. Second date with a super nice guy but zero chemistry for me (my mom had been giving me grief for never giving anyone a chance, this was me giving someone a chance). We are walking out after drinks and at the point where we break off in different directions we pause to talk. At some point he goes in for a kiss that I was not remotely expecting and I literally made an “AGH” sound and physically head bobbed out of his range. I don’t even want to know what my facial expression was. Sorry dude.

  27. Sandra says...

    My most awkward date was a set-up through a friend of a friend. “He’s a great guy! I think he would really like you! He works with troubled youth!” But he also lied for fun. We talked on the phone before we decided to meet in person and he would ask me things like “So, do you have any problem dating someone who is divorced?” When I started to answer he interrupted with “Just kidding, I’m not divorced!” Then he asked if I liked dogs, and pretended to be calling his dog “Come over here, buddy…” But just kidding, he had no dog. It was like an SNL skit. Huge red flags/what the hell was I thinking, I agreed to go on a date with him. He rode his bike to my place, but wouldn’t leave it on the street. He also didn’t want to leave it in my bike room…he wanted to bring it to my apartment. On the 6th floor. But he was afraid of elevators (so am I, but I don’t pull that out on the first date). So he carried it up 6 flights of stairs. We went to a street fest where we ran into an old friend of his, and he lied and told the guy we had had been dating for 2 years. But he never corrected that one with a “just kidding”. The conversation was horrible. He said, “I hate small talk…why don’t you ask me what I think about abortion?” And we still had to go back to my apartment to get his bike. (Such a bad decision on my part to let him put it in my apt.) Worst date ever.

    • Lynn Nguyen says...

      Oh dear that’s awful. Does the insecure red flag get bigger?

    • Allegra LaViola says...

      I really think you deserve a prize for getting through that one!

    • Caitlin says...

      Funnily enough, this seems to be a common thing. I’ve had platonic guy friends try to pass me off as a date when we bumped into ppl they knew, or at least not bother to correct them right away when the other friends went into “And who is this?” *wink wink nudge nudge* mode. We were just out to a friendly lunch! On a workday!

      Another time a sweet guy asked me to come along to check out this great new foodie place he’d found, which happened to be pretty near my house at the time. I’d had a crush on him a few years prior but by then we were (to me anyway) strictly platonic as my love life was already plenty complicated, so I thought this was a regular hangout session. Another mutual friend who was supposed to come had dropped out, but I didn’t think anything much of it. We arrive and I realize it’s a full-on “date” when I discover the place is fully romantic — think sumptuous Balinese decor, tinkling little water fountains, perfumed incense, gorgeous gazebos set in manicured gardens with dimmed lighting and hushed music! It was then I realized he was probably just sweet on me. Somehow I powered through dinner as just friends, because I could see that he was really nervous and I didn’t wanna blow things up in the (unlikely, but still) event he was going to pull out the “who said I was interested in you? Get over yourself!” card, and I did still like him as a friend. Granted this was not regular “friendly” behavior but I wanted to keep him as a friend and let him down gently. Also there was no Uber back then and this was a pretty quiet part of town with no cabs or public transport. Later I happened to mention the dinner to our mutual friend and he was like, “He took you where?! Oh man he’s totally into you, couldn’t you tell?” Yes. Yes I could tell but I didn’t feel the same way exactly and I was already head over heels for someone else! At any rate, I married the person I was madly in love with and the sweet guy (who has a great gf) and I are still friends today.

  28. Emily Getty says...

    My freshman year of college I was really excited to go on a date with my crush. I don’t remember much about our first (and only) date, but I do remember that he told me he’d rather be with his friends watching whatever sports game was currently on TV. I believe my jaw hit the floor.

  29. Elle says...

    In high school I went on a date with a boy who was waiting to kiss til marriage (that should have been my first red flag, but for some reason I was very into him). He wanted to meet at the lakefront for an outdoor movie, followed by dinner. Romantic, I thought! I had just gotten my driver’s license and was terribly directionally challenged so I printed off mapquest directions to the waterfront. (Hallelujah for gps now!) Naturally, I got lost, and ended up in Delaware (I lived in Maryland) and had to have my parents come get me so I could follow them back to the waterfront. When I finally arrived to the date an hour late, the movie was mostly over. It was SPONGEBOB so I chalked that up as a win. Who goes on a date to the spongebob movie?! We held hands awkwardly and then headed next door for dinner where my date had invited 4 other friends to join us. Definitely unexpected. But the real kicker was when he took off his shoes, and sat cross legged on the bench, hairy toes just hanging out, then announced that he was going to stay and eat with his friends and said goodnight. I am sad to say, we actually ended up dating after that. Never kissed though!

  30. Annie says...

    I had been chatting with a guy on a dating app for a week or so. As I walked over to the bar where we planned to meet, he texted me that he was running about 15min behind. I got to the bar and ran into a group of friends warning them that I was meeting someone for a first date and might need rescuing. Dan arrives and I watch him approach someone else at the bar. I walk over, greet him and he immediately says “Hey, I’m sorry I’m running late, I have irritable bowel syndrome and it really slows me down.” No judgment against IBS but why would that be the first thing you choose to share?! I order a drink and ask him if he wants anything – he doesn’t drink and can’t really eat anything on the menu because of his IBS. This continues to come up in conversation for the next hour or so.

    After latching onto my friend group for a while and struggling through conversation I decide it’s time to put an end to it. I tell him I have to go home because my roommate is sick so we both walk out and part ways. Once he’s out of sight I turn right around and hang with my friends and end up having a great night.

    A few weeks later he follows up on Valentine’s day with two GIFs: 1) I want to touch your butt and 2) I love you more than pizza.

    Why!?

  31. Katherine says...

    Before I met my husband, I tried online dating for about a month. For my first date, I met with a man at one of my favorite restaurants. During the meal, he told me that he does not like Catholics (after hearing that I teach at a Catholic School) and then suggested that we climb a fence and break into a Civil War cemetery after it got dark. After the date was thankfully over he called me and wanted to know when we could plan our second date. I politely declined seeing him again but kept thinking how he could have thought that the date went well!

    I went on another awkward date that ended with the guy getting into a fender bender after he dropped me off at my apartment. The worst part was trying to decide whether to linger and help out or leave since we both knew the date did not go well.

  32. Eileen says...

    I had started reading these comments yesterday and it reminded me of something that happened to me in high school, and I was actually feeling bad about how things had gone, but now I’m realizing I have nothing to feel bad about! sorry for the long read… it’s not an awkward date, but it IS full of teenage angsty awkwardness!

    The story:
    When I was a sophomore in high school, I had a creative writing class that was a mixed grades class. I was sweetly naive back then, and would often catch a classmate (lets call him Joe) staring at me when we were supposed to be working on our writing (and I would often be in a focused dream state). I was always embarrassed I got caught staring off into space, but didn’t think more of it. We were friendly, but not really friends and didnt have many conversations outside of class.

    Well, prom rolls around and, since it’s reserved for Juniors and Seniors, I didnt give it much thought. So when my TEACHER handed me a note, I was truly confused. This was the first clue in what turned out to be a multi-location scavenger hunt around our school with several of Joe’s friends/classmates handing me the next clue, and it all ended with with Joe asking me to Prom. oh man.

    This should have been a huge moment and the ultimate cute start to a lifelong love story, if only I had the slightest interest in a romance with Joe. I said no thank you in the most gentle way a 15 yr old with no dating experience knows how to, and speed-walked away.

    Even back then I wanted to say yes because Joe truly was a sweet and good guy, and if for no other reason, the sheer effort and amount of people involved! but being so caught off guard didn’t give me any time to talk myself into anything.

    Still had the rest of the semester to finish class with Joe and the teacher! Real or imagined, I felt like my teacher was disappointed I turned down a sweet guy. Also, ended up at prom with another guy. I’m the worst.

    • Jessica O. says...

      no, no, no!!! you’re normal (though not the norm, sadly) and every woman should feel 100% confident in saying “no thank you” to a date ANYTIME, FROM ANYONE, NO MATTER HOW “NICE” THE GUY IS. us women, from sooooo young are conditioned to “just give him a chance” and that leads to awkwardness at best and sometimes sexual assault and dangerous situations at the worst. we do not owe our time, attention, or bodies to anyone just because they ask nicely!!!!

  33. I married the man who turned what could have been a non-date or bad date into one of the best dates of my life. I had been to the physical therapist in the morning and had a terrible, raging dizzy, spinning spell. The PT sent me to an ENT who recommended an inner ear exercise (to reset the tiny bones in my inner ear). I planned to cancel my date that night. I was feeling so terrified that I might have another dizzy spell and I was definitely not feeling myself. When I tried to cancel, he said, “Let me call you right back.” When he called back, he offered to take me to my ENT appointment. He had educated himself about the inner ear and had some thoughtful questions for the ENT. He held my hand while the ENT tilted my head back to induce a dizzy spell. I was myself. This was me – full of fear! My date stayed. He saw the raw fear, he watched and learned how to do the inner ear reset. He took the info sheet from the ENT and promised to help me do the reset, every hour throughout the day. He invited me to reconsider our dinner date. “I think you can still do it,” he said. He knew how much I wanted to eat at this special place. I had made reservations months in advance. So, we decided to try it. He packed blankets in the trunk and set the timer on his phone. Every hour, he was by my side, holding onto me, talking me through the spinning that ensued from the reset exercise (with me on my hands and knees). Next the the road, in a parking lot, behind the restaurant, on a patch of grass… I clung to him, whimpering at times, until the spinning subsided. Between the hourly reset exercises, we carried on with our date. We had amazing conversation, fabulous food, and lots of laughter. I was completely shocked at how kind, helpful, understanding, and calm he was. My fearful reactions to dizzy spells did not scare him away. I felt genuinely seen and cared about. He had seen me at my worst, and he did not run away. We’ve been married for almost 3 years now, and he is absolutely the VERY best!! My dream come true.

    • Annabelle says...

      This made me tear up!

    • Siiiigh. This is so lovely.

    • Kate the Great says...

      Awwwww. I love how this WAS awkward, but it ended up being positive.

    • Marina says...

      It gives us, who had wxperienced so many bad stories, such hope! Thank you for sharing!

  34. Cecilia says...

    Earlier this year, I went on a date with a guy whose mom was in my friend’s Bible study. My friend really wanted to set us up and talked him up (despite having never met him) quite a bit. So we met for coffee.
    My friend had told me that he was a freelance writer who was working on becoming a coder or already was a coder because that was a better way to make money. Turns out? He wasn’t trying out coding at all; he was just a freelance writer who couldn’t make enough to make ends meet and was living in his parents’ basement. But the absolute deal breakers were a) when he told him that he doesn’t believe in democracy but only absolute monarchies (and then went on to tell me everything that wrong with the royal families of Europe) and b) when he told me that he doesn’t believe in health insurance and his life goal is to live in a van (with his large homeschooling family) in Wyoming.

    He makes a great story. I don’t think that he should date anymore; he’d be a good hermit.

  35. Emily says...

    I can’t remember the particulars, but the summer before my senior year of high school this dude called my house (those were the days!) and asked me out to dinner. He showed up with flowers for my MOM (“Hi, Mrs…!”) and proceeded to take me to his “favorite date-night restaurant” at the top of a downtown hotel. We were the youngest people there by a solid 45 years, which was embarrassing enough, but then he…I can barely even type this, I’m cringing just remembering it…he…played the baby grand piano by the bar. Candlelight, mid-size southern city twinkling below on a summer night, every grandma in the place swooning, me burying my face in my cloth napkin. I’m pretty sure he busted out some Elton John, and Elton John he was not.

    So nice, so earnest, so awkward! I was 17 years-old and practically mute with embarrassment the entire way home. I don’t think we ever spoke again.

    Flash forward to me recounting every detail to my BFF, who admitted he had taken her on the EXACT SAME DATE a year or two before! Some guys have moves, some guys have just one move and hope it’ll land on the right girl. Hope he found her :)

  36. Megan Lec says...

    My worst date still lives on so clearly in my mind even though it occurred almost a decade ago. In college I was a part of an outdoor club that spent weekends backpacking, climbing, and canoeing. After a fun trip canoeing, one of the guys asked me on a date, and although I had a huge crush on his best friend, I agreed. I had not dated much yet in college and I was truly excited for our date. I lived in a dorm at the time and my floor of best friends all helped me get ready. The date went sour quickly, he wouldn’t let me order for myself, even ordering my drink for me without asking what I would like, and within about 15 minutes I was ready to be home. The majority of the night I spent basically counting down the moments to lament how quickly this date had turned into a nightmare. When we arrived back at my dorm, he leaned in for a kiss and I quickly gave him a hug and booked it out the door. I spent the next hour gabbing with my girlfriends and laughing about the audacity. As we chatted I got a follow up text from him ASKING WHY I HAD NOT KISSED HIM. As I read it aloud to my group of friends, our anger at his belief that I OWED him a good night kiss bubbled over. I can’t remember how I responded to that text and while that date did not go the way I expected, I remember most the shared laughs and support of my girlfriends.

  37. Betsy says...

    I laughed so hard at the dog park Mike comment. I’ve been with my own dog park Mike for 2.5 years now. We met at a local lake, with a dog park at the swimming beach. Our pups were about 3 months old at the time, He stalked me for my “great legs”, blue eyes, and my tenacity for trying to get my pup to try out the water. My tenacity worked, my pup is a swimming fool. We still go to the dog park 3 days a week to go swimming.

  38. Capucine says...

    My best friend’s mom shared that an uncle asked her to get him my number. I was SEVENTEEN. His niece’s friend, I had known him since I was a kid! He was at least forty. Word got out and everyone was disgusted. I see him at her family gatherings to this day and just…awkward. Forever.

    • janee says...

      The way older men feel comfortable and oblivious to the inappropriateness of their interest in young women baffles me. The 1300’s are over guys!

  39. Kate says...

    I had a mix up like this with a Brian from work, who I thought was Ryan from school when he called. Needless to say, it was very awkward when I figured out the mix up, and even more so when he took me by his church on the way home after dinner and made a not-too-subtle joke about asking if I would be interested in learning more about his faith. (I wasn’t.)

  40. Anon says...

    The worst “date” I ever had was the time my best friend asked me to join her and her boyfriend on a scavenger hunt organized by their church. I was newly broken up at the time so I thought oh how nice, they’re asking me out on a fun outing. I knew him too so I had no qualms about being the 3rd wheel. Or so I thought! Turns out they’d arranged to have another guy ride in the car in the back seat with me. It was a setup. What’s worse, this guy was “special” but high-functioning enough that he was perfectly capable of believing AND acting like he was God’s gift to women and that any girl should be so lucky as to be his servant. He was utterly patronizing, condescending, belittling, and so thoroughly unpleasant that I almost broke up with my best friend over it! Of course she said it was her bf’s idea but I was still beyond furious that 1) he thought I would be into that misogynistic a-hole in any way, shape or form, and 2) that she knew and went along with it! It was so insulting that her bf actually thought that guy would be a good match for me that I couldn’t even stand to look at him for a long time afterward.

    • Anon says...

      If he had a special need (and is high functioning) then there’s no reason to put it in quotes. It just demeans. If you’re saying he thought too highly of himself and therefore felt he was special, well, then you could’ve said it that way.

  41. Patty says...

    A guy asked me out in front of all my friends, so I said yes (because I didn’t have the heart to say no in front of so many people.)

    He called me the next day and left a voicemail offering up 3 choices of nights we could hang out, with 3 DIFFERENT OPTIONS of things to do. I.e. “We could hang out Sunday night and go bowling, or get dinner or go to a movie, on Monday night we could have sushi in Harvard Sq, rent bikes, or have Italian, on Tuesday…”

    I chose the sushi on Monday because it seemed like the smallest time commitment. But turns out, he *knew* the sushi chef. We had a special table to ourselves and the chef gave us a special menu full of raw fish and octopus tentacles. (I don’t actually like sushi, I was planning on ordering a California roll).

    Then he told me that I was the first date he had been on… since his girlfriend died.

    I ended up taking the wrong train home on purpose so I could avoid more bombshells being dropped. I felt so awful. It was an awkward date for me, and I assume pretty rough for him as well. It definitely showed me never to say yes out of pity because it does nobody any good.

  42. Katja says...

    Two dates come to mind –
    I met this guy on a local contact website. He seemed nice, email exchange and brief phone conversations were ok, we went out on a first and second date, not spectacular, but normal enough. On the third date at an Italian Restaurant he suggested to take me on a trip with him (he was a diving instructor) for a week. When I politely declined and told him that he was moving too fast for me, he started getting very flustered, ate my pasta (claiming that would calm him down) and generally went into a rant how all women wanted to just be friends with him and never enter into a relationship with him. I was so shocked that I tried to actually reason with him instead of leaving right away. The next day he called me and apologized, wanting to still take me on the trip. I told him no – and no friendship either!

    I also went out with a psychologist once (for drinks) who on the first and only date spent the whole evening telling me about his six year (!) relationship with his ex, who smashed his furniture twice (!!) and who he should have dumped after a few weeks but didn’t because he did not want to be the bad guy… When we paid, he split the wine bill, but made a big deal out of paying for the whole bottle of water we had had (in Germany, you don’t get free water in restaurants). I never saw him again…

    • nadine says...

      Hahaha eating your pasta to calm down is hilarious.

  43. Awkward date! Got to chatting with a guy on the bus and we made a date for the next weekend. I didn’t think it would be amazing but he seemed charming, and I was curious. He is enthusiastic, sending multiple texts (“I can’t wait for our date, can’t wait to see you”, etc.)
    Cut to:
    He suggests a Marina district karaoke bar that runs bad homemade commercials on TV. I counter with a bar on Polk Street (the Hemlock, RIP).
    We meet up. At the bar he implies that we’re slumming it, tells me he thinks Trump will win the election because his “generals are all such smart guys” (this is pre-election, obviously!), and talks about his love of first person shooter video games. His primary interests are playing video games with his roommate and getting food delivery. The conversation is stilted. Loooong silences. He does not tip the bartender.
    After half a drink I know this isn’t going anywhere good. Still, the night is young, and so are we.
    We get dinner (he pays, and I did not have any qualms about letting him do so) and then head home. He gets out at his bus stop, I get out of mine. He keeps texting/calling for a week even though I tell him honestly that I’m not interested in seeing him again.
    A few weeks later, he hits on a friend of mine who is basically my doppelganger, and then tries to pick her up a second time shortly thereafter.
    Fred, if you are out there, you make a good story…

    • Megan says...

      OMG . Was Fred an artist?? I think I went out with him too!!

    • Cassie says...

      The Hemlock is gone?!? So sad.

  44. Erin G. says...

    Newly single, I was out in the world trying to make some non-APP magic happen and actually met a nice guy at a bar. We chatted for a few hours, but near the end of the night, he abruptly left without explanation. A week later, I get flowers delivered to my office from the mysterious disappear-er with a lovely card asking me on a dinner date. (I cringe now to think of how sweet I thought this was instead of how creepy – he didn’t know my last name or where I worked .)

    We meet at a wine bar for a drink and within the first 15 minutes of conversation, the following things came out of his mouth:
    1. I had to pay that bartender to lift your last name off your receipt.
    2. I don’t date anyone until I run a credit check on them. Good news: you passed.
    3. Have you Googled yourself? Your digital footprint is pretty big.
    4. I have your home address, too, but figured flowers showing up there might scare you off.

    OH, THAT IS WHAT MIGHT SCARE ME OFF?

    Slapped down a $20 and left (after guzzling the rest of my glass of wine – I needed it).

    • Mari says...

      That’s so damn scary.

    • Cg says...

      I hope you reported that bartender to his/her manager. They out you in some potentially serious danger.

  45. HH says...

    He waved to me from across the empty college cafeteria. He was cute. Amused, I waved back. He joined me at my table and started talking. I thought, “How funny, he thinks I’m my twin.” (It happened all the time.) He walked with me to class and outside my building said, “I’d like your number. We could go out?” Because in those days I was unable to say no to someone to their face, I handed it to him, but laughing, said, “You can have it, but I’m not who you think I am.” He looked confused. (That always happened, too, following this statement.) “I’m not Em. She’s my twin,” I said. He said, “You have a twin?” A feeling of horror expanded from the pit of my stomach. In addition to cute (from a distance), he had been strange.

    And that the “meet cute” that quickly unraveled into one of the most awkward and awful dates of my life. It was the age of landlines. The time when you couldn’t text your sister, “Do you know a cute but slightly creepy guy who wants to be a paleontologist?” But also the time when you could choose not to answer the phone and (without caller ID) not know who you had “missed.” Ha.

  46. Shannon says...

    In short: We had a lunch date. A kiss felt far too forward and I’m not a hugger. So, I shook his hand goodbye.

    Yet, somehow, here we are years later still together. Maybe that’s secret, folks: always end your first date with a handshake!

    • Michelle says...

      So funny – I ended a first date with a side huge…and we ended up married too!

  47. Jess says...

    I finally started dating my longtime college crush my junior year. Three years of mutual desire led us to a small state park outside of school grounds after dinner (our school was very strict, no PDA etc). Surprisingly, steaming up the windows is a real thing. All was going well until the cops showed up and shined their spotlight into the cab of the truck. I was like who in the heck is shining their headlights, how rude. The officers told us this was state land and we needed to get lost. We went and found another spot to pick up where we left off in a empty park in town. Cue completely steamed up windows. Then ANOTHER police car comes by. I remember the conversation clearly because the police officer asks how everyone was doing. My boyfriend (now husband and father of 2!!) answered “fine”. But the police officer said “how about the lady?” He wanted to hear from me, that I was okay. My husband was mortified but I was delighted.

  48. AC says...

    I feel fortunate to have been of dating age in the Philippines, where you start out on group dates first. So there is a lot of buffer + protection. Altho I did have to go on my share of awkward dates to be the +1’s +1. Also back then they still did the “courting” thing where the guy would call a lot just to talk and then visit with flowers/chocolate etc. and hang out at your house. It was all really traditional and TBH I never ended up dating any of those guys long term. Still friends with some of them tho, so maybe the courting thing works to set a good foundation?
    Not an awkward date, but v. fun and drunk: I can’t remember if we ate dinner or not but we ended up at a now-closed dive bar where we got drunk, made out at the bar, and then he proceeded to chase me around the block screaming (both of us) and then we fell into a pile of garbage bags. He’s married now with 3 kids, so he’s settled down, thank goodness!

    • AC says...

      It me again. All these stories are triggering so many memories! Also not an awkward date, but I do have some awkward pick up stories. Oh NYC, I love you:

      * At ‘ino on Bedford (RIP, wine bar of my dreams) I was sitting at the tiny 3-seater bar reading a magazine and having wine and bruschetta. There was a stool between me and a much much older gentleman who seemed to be another regular. He turned to me and started trying to talk to me (I am reading, dude!) asking if I’d been to Korea and saying how much they loved him there. I guess he was a science journalist? I am Chinese so I guess he was assuming that I was Korean? Anyway I tried to answer politely but with one word answers so he’d get the point. No dice. He asked if I’d like to kiss. I pretended not to answer and said, “The band? I don’t really listen to them much.” AND THEN HE CORRECTED ME. NO, WOULD YOU LIKE TO KISS?? I hailed the bartender, threw my money down on the bar, and left so fast I knocked the stool over.

      * at a ramen spot on 3rd Ave (also RIP), I was sitting next to another solo diner. He asked the server what was playing on the stereo and I couldn’t help myself. I said “It sounds like Gang of Four.” People, never NEVER make reference to obscure-ish post punk bands. He asked for my email address which I begrudgingly gave, then took a second to look at it and tell me that I had interesting handwriting and that he’d like to analyze it. I wonder if he actually did because I never heard from him.

      * I had met a barback shortly after splitting from my long term live-in boyfriend. He had just broken up with his first love (he was much younger). We had known each other very marginally for a few months at that point. Anyway he had the bright idea to do ecstasy together (this was the early 2000s). We met up with some friends of his and they spent the whole night reminiscing about him and his ex. I hope they got back together because she sounded sweet and he was actually a super decent guy.

    • Candace says...

      AC!! Fellow Chinese girl from an ASEAN country here!! Omg I can so relate to the “group dates” and the “courting” of patents, although that happened more to my sis than me (she had a ton of suitors in high school). I’d regularly come downstairs to find some guy or other reading the papers with my dad and talking politics with him, while my sis hid out in her room to avoid them! 🤣

      This is triggering all sorts of memories of going along on girlfriends’ dates as a human shield/buffer and asking them to come on the rare occasions I had someone ask me out. And how the dates were always to the mall! 😄

  49. Amelia says...

    It is a long story as to why this came about, but the punch line is that I didn’t go on a single date until I was 20 years old. Understandably, when it finally happened, I was nervous, so he arranged it to be a double date with my roommate and his, who were just friends tryna be good wingmates.

    Ok, where’s the awkward part? For starters, the only date everyone was available was Valentine’s Day. And the location? Nebraska Furniture Mart. (He needed a new bedframe and thought this was a great time to shop for it.) There were also chocolates and vaguely misogynistic cards thrown in. So my first date was a double date at Nebraska Furniture Mart, shopping for a bedframe for my date while our roommates lurked in the background watching for a spark. Needless to say I took more of a frontseat in my dating life after that.

    • KC says...

      !!!

      This is amazing.

  50. anja says...

    When I was veeery young, I met a guy who had placed and ad in the paper (those were the days, eh?), saying he was an artist who looked like Nicolas Cage. An artist he was, but mentally unstable, so I excused myself and went home. Fast foward a few months later, when I met a guy I really liked and ended up living with for 7 years. On our first date we found out that the artist guy was his flatmate. So. very. akward:-)

  51. Nina says...

    hahaha that is so funny.

    Mine was a series of dates. With the same person. I was young – 19ish – and yet, 30 plus years later I still have a hard time saying NO to someone I have NO interest in because I imagine how hard it is to put yourself out there and ask someone out! (oh and I might have initially said yes because he had a cabriolet convertible and I wanted to ride in it haha).

    So…he was my stepfather’s (very nice man) cousin. And he worked with my sister at the ambulance. Plus, I worked with his Uncle who was a super cool guy so I thought he must be cool. I was walking through the parking lot at my work (a grocery store, I was in high school) and he drove past me. I was said hi and he slowed down and was talking to me. I made fun of him for having little crossed golf clubs on the sides of his car with his initials (so preppy and ridiculous!). He laughed and said I was cute and asked me out for dinner. I said sure.

    He arrived in his volvo. WHAT!???? No one wants to ride in a volvo for a date esp in the late 1980s when they were super uncomfortable. He got upset because I didn’t sit in the car and wait for him to open my door and I opened the door at the restaurant. We went to a trendy restaurant in Chestnut Hill (a very hip place outside Philly) AND THEN he proceeded to tell me about the long time girlfriend and their relationship and how he thought they would get married AND then he started to talk about his dead father AND THEN he started CRYING.

    Remember HIP restaurant – so the tables were like inches from each other. And everyone was looking at me like I did something. And he’s saying “I feel so comfortable with you, I never talk to anyone about all these things or cry like this!” and I’m thinking “OMG stop crying…I don’t know what to say…I hate being here” so then he takes me home. at that time I had a cat who would run up to me whenever I got home.

    He didn’t like cats (another strike against him added to the volvo AND the crying AND that he was a black republican which in my 19ish year old brain was a total oxymoron) so the cat runs up, I pick her up and he backs away THANK GOD because I was sure he was going to kiss me.

    And then (to my still utter shame and embarrasment) I agreed to AT LEAST two more dates. One we went to a jazz ensemble (my least favorite music at that time) at a hotel down in Philly…again, I was like 19…so this wasn’t fun for me. oh let me sit here listening to this music and drinking a shirley temple. yay! and praying the whole time he won’t start crying again. AND we drove in the volvo again!

    the last time I was like “you know I really want to ride in your convertible” so he was like “ok we can go out for ice cream” I was like ok, can I bring my little sister? (she was 14ish) he agreed. ON THE WAY THERE they got into an argument about politics. And he literally said, “women shouldn’t discuss politics.”

    I was like UM WHAT? and he went on about how we shouldn’t stress our brains etc. THEN we got to the ice cream place and he sits so he can watch his car. AND THEN a group of kids walk by his car and they are looking at it…(because it was cool back in the 80s) and he gets up to go out and tell them to NOT TOUCH HIS CAR and MOVE ALONG. My sister is FURIOUS about the women and politics thing PLUS we were not republicans and would never agree with almost any of their policies.

    Each time we got home the cat would run up and one time he was all “aren’t you going to let me kiss you” and I was all “oh haha probably not.” so awkward.

    I finally went back to college so didn’t have to say yes or no anymore and then I just wasn’t home when he called. He got back with his old girlfriend, they got divorced, and he’s currently single. why do I know this? Because my MOTHER still thinks we might get together and says he asks about me all the time and my sister (older one that he was working with) is still friends with him on facebook. gah…

    • Amy says...

      Umm @Nina please keep writing! Your way with words and flair for the details are incredible! Thank you for making me chuckle as I scarf down lunch at my desk during an incredibly steamy summer Friday.

  52. Kate says...

    I met up with a guy I met on Bumble around the holidays.
    He said he loved music, so I asked what kind.
    He said, “I love Adele” and I was like, “OH yeah I like her too” :)
    He then proceeded to SING to me from across the table the entire chorus of Rolling in the Deep, very badly and very seriously. I sort of smiled nervously, very aware of what the couple at the table next to us must be thinking. After he finished, he smiled proudly and said, “If this goes well there’s more where that came from.”

    • K says...

      Okay, this one is priceless.

    • Anna says...

      Thank you for this priceless gem of comedy told succinctly and very well. I needed that laugh!

    • Vanessa says...

      That’s a wonderful line, f this goes well . . .

    • Anne Knapp says...

      This is just wonderful!

    • Joanna Goddard says...

      hahahaha

  53. OH MY GOSH! My mom recently told me this story, which I don’t remember so I must have blocked it from my memory, I am not even kidding! When I was a senior in college I worked at my local Abercrombie & Fitch and this guy that worked there was kinda nerdy and quiet and from one of the more rural areas nearby. He asked me out to dinner and I always had a hard time saying no to people’s faces about first dates, so I said yes…. I met him at dinner only to find his entire family there and he introduced me as the girl he was going to marry. SO AWKWARD. My mom said I called her the next day to tell her all about it and how horrified I was. I remember how awkward he was but I seriously can’t recall the details so I am glad I called her to tell her about it!!!!

    • Rezia says...

      Whatttttt! That’s traumatizing!

  54. Sheila says...

    I love bad date stories! My worst one ever involves a terrible dinner while being blinded by the sunset, and then awkward salsa dancing lessons in an empty bar on an oppressively humid night in July. He was trying way too hard. Trust me, it’s a doozy. But just recently I went on another bad date that might take the cake to that night back in 2008. I met this guy “Matt” online. We seemed to have a lot in common, even had some mutual friends and worked in the same field. I asked our mutual friend about him and he said he was a good guy. Matt made me drive to him, because he didn’t have a car at the moment. Ok fine, I’ll drive to the Cape on a Sunday afternoon in June. He also said he was in between apartments, so effectively homeless. We played pool and darts, which was fun EXCEPT for the lack of stimulating conversation. He made no attempt to get to know me, and seemed to be dodging answering questions about himself. At the end he paid, and I was sure to thank him. His response: “Well I didn’t see you pull out your wallet.” My incredulous retort: “Dude, I drove down here!” He claimed to be kidding, but I don’t think he was. I’m 99% certain he was drunk during the date, and not in a fun way but rather a he-has-a-problem way. He texted me sporadically after that, and even said he had a good time and if I was ever down the Cape again we should hang out. I politely declined and promptly deleted his number. At 38, I just don’t have time for that anymore!!

    • Lauren says...

      😲 this must be a type b/c I agreed to a date with a hot guy I didn’t know, and slowly over the course of our date realized he was… homeless, and then… an alcoholic.. and then, when it became obvious that there wasn’t going to be a second date, he changed tacks and asked if he could sleep in my roommates’ and my spare room! They weren’t coming home till late, and Reader, I let him. 🙈 I’ve always had a bleeding heart but I’d like to make my 20-year-old self understand that, come on! You are allowed to have standards! You don’t have to hire every single person who comes for an interview!

  55. Jas says...

    I had online date, we met on chat (ah, that old days :-)) ). While we were chatting he said that he is very handsome, so I expected, I don’t know, somebody like Paul Newman when he was 30 years old. Well, reality :-)). When I saw him, the first sentence which pooped from my mouth was: ” You’re handsome only to your mother!”.
    I was really disapointed :-)).

    • Helen says...

      Imagine going on a first date and the first thing the person says is a negative comment about your looks? No one likes to be disappointed but there’s something to be said about those who can show kindness and politeness during those times. I hope to never go on a date with someone who would act as inconsiderate as you.

    • Anna says...

      That’s so cruel…

  56. Marianne says...

    My first ever Tinder date was with a guy, who turned out to be married, a dad AND was in an open relationship, three “details”, which he conveniently saved for our first (and last!) date.
    He told me right after we had ordered coffee. I should have ended the date right then and there. Unfortunately, I suffer from ‘nice girl syndrome’ so instead, I stayed and talked with him for a couple of hours.

    • Shayna says...

      This happened to me except my date was a CHAPLAIN! and he waited until the end to tell me. No wonder he wanted to meet in a town half an hour away. I was so upset I promptly scolded him and told him he should be at home with his wife and kids. Skeevtastic.

  57. Kahani says...

    I used to be an awkward ugly duckling, so unless the guy straight-up terrified me, I used to say “yes” to at least one date as much as possible because I remember being awkward and feeling unattractive and I wanted to give everyone a chance. This has resulted in some very good friendships, a few great dates and a LOT OF VERY BAD DATE STORIES.

    There was the guy who could not use chopsticks or eat spicy food but of course, ordered spicy noodles and insisted on eating with chopsticks. He wept and sweated while painfully and mostly futilely pecking at his noodles.

    There was the one who saw me walk out of my house in heels, got upset that it made me as tall as he was and asked me to go back in and change into flats. I did go back in, but I refused to go back out again.

    Or the one who, in the getting-to-know-you phase of the date, stopped me mid-sentence to say, “I don’t read books. Can we not talk about things I don’t know about?” I left as soon as I could.

    This could go on. But I must end with the one who jumped on a chair and screamed hysterically at a cockroach. I killed it for him, but well. He never asked me out again.

    • Laura C. says...

      Your dates cracked me up Kahani!

    • Amy says...

      These could be made into a television sitcom!

    • omg I’m giggling out loud at these

    • Kahani says...

      Aww thanks guys!

    • Annie Knapp says...

      Hysterical! I’m seeing a montage set to music….

  58. Heidi says...

    It was the first time my Boyfriend took me to bis parents, ist was nice and we stayed overnight. Next day I use the bathroom, normal routine, all is well, or so I thought. I flush the toilet but IT wont get down. It just wont and sorry I use a normal amount of paper. Desperate I try everyrhing but finally have to ask my Boyfriend for help. He stands there trying to flush my poop down. It was so embarrasing, nice guy made jokes and we both laughed trough it. Now we are happyly married with two Kids. If one can get though that laughing he is a keeper, bad date aside…

  59. Babs says...

    A friend who lived a very different life than mine (married young, loads of money), convinced me to go on a date with her husband’s friend from work. Not the type of guy I’d normally go for – investment banker, from what I could gather from my friend not a lot of mutual interests in common, etc. Still, I agreed to meet him for a double date with said friend and husband. He showed up – with 2 other women. Two other very young (and we were quite young at the time), very inebriated women he’d met at a bar prior to the date and spent most of the day with. He then proceeded to introduce himself to me and act like this was perfectly normal and converse with me like the first date was going well and as though there weren’t two other women quite literally hanging off of him.
    My friend was mortified, her husband acted like this was perfectly normal, and I, for the first drink, sat and mumbled answers as I couldn’t decide if I should be angry or just laugh at how ridiculous it all was. Funny enough, what I remember most is we were at a sushi restaurant and one of the women kept asking the server if they served spaghetti because she didn’t like rice. Needless to say, I didn’t stay for dinner.

  60. Anna says...

    From overseas here. But it baffles me that many comments seem to assume that the guy should pay for dinner date? And no offer to do so equates bad date… why?

    • Char says...

      I think it depends on what part of the country you’re from and what era you grew up in. I’m from the US and I was surprised by that too!

    • Ll says...

      I once went on a dinner date with a guy who ended the night by asking for a blow job. When I laughingly asked why I would do that he answered “I bought you dinner”. Since then I make sure to split the bill or pay the entire thing myself to make a point.

    • AE says...

      Whoever asks…pays, states tradition/patriarchy/etc.

  61. Jenn says...

    I don’t have much time to date so I rolled the dice and scheduled two dates on the same night. My friend had been giving me a hard time about not updating her while on dates, so when date number went stepped to the restroom I texted her “Going ok. Luckily Coach is running behind.” Only I did not send the text to my friend. I sent it to date number one in the restroom. So embarrassing! He was a good sport and joked that we would have to tell the story during a toast if we ever got married.
    I will never double-book again!

  62. G says...

    I once went on date / non-date (met up with a new friend I had a crush on and thought he was taking it to the next level) where the conversation was so stilted that I opened a book to read it in the bar during a particularly long lull. Shortly thereafter I said my sister’s flight landed early and I had to go pick her up. Truth was, she wasn’t landing for another two hours. What to do? I went to the grocery store where I RAN INTO MY DATE at the checkout line. His response? “Well this is awkward.”

  63. Caitlin says...

    Haven’t thought about this in YEARS… went to a concert with a really sweet male friend in high school and the topic of first dates came up and I admitted I’d never been on a date and he was like “… but this is a date!” I was horrified and oblivious and he was kind but also obviously horrified. Ahh youth.

  64. SuzieQ says...

    All first dates:

    * Man who showed me a picture of his gorgeous, model-esque ex girlfriend and said “if she was into me, you should be.”
    * Guy insisted he was “legally declared half divorced” (I’m a lawyer; that is not real a thing.)
    * Guy who told me he was “like the Long Island Medium for f*t people” with a dieting-based nonprofit.
    * Man who dismissed me from the table at our dinner date when I wouldn’t agree to a second date—because he was MARRIED.

    • janee says...

      brutal. i’ll pray for you

  65. Annie says...

    Oh gol, these are priceless. Equally depressing, hilarious, and validating!

    Two dates come to mind for me… The 1st was with a friend of a friend I had met once prior. We went to dinner, all was going well and I was enjoying myself until as we were strolling through old town afterwards he insisted we go into a bar that had his favorite video game which he had mentioned at dinner. We went in and I played first. It was that hunting game, where you shoot forest creatures with a rifle. I’d never played before, but hit most of them (thanks childhood Duck Hunt practice). I handed the gun over to him and he started shooting, he hit some then started missing and immediately turned into a grown man-child and threw a legit tantrum. He screamed at the game, cursing up a storm, slamming the rifle down on the game and continued dropping f bombs every 10 seconds or so. I was in awe, shocked and didn’t know what the heck to do. Everyone around us seemed to feel the same: jaws on the floor. Felt like I was in a bad romcom!

    2nd story… Met a guy from Tinder at a restaurant at 6pm. He says he’s not hungry so he orders a chai. I don’t want to sit there and eat alone so I order the same, even though I’m pretty hungry. Not a terrible date besides the annoyance of a non-dinner dinnertime date! But, I enjoyed the conversation so I agree to a 2nd. We meet up again and get coffee and walk around the neighborhood. My stomach felt off most of the day but still opted to go. I told him as much when I arrived, that I didn’t feel great but thought a walk would help me feel better. So we walk around the neighborhood, going into shops, chatting, laughing. Then after 2 hours have passed, I tell him my stomach is feeling a little worse and I think I should go home. He says okay, we say goodbye. I’m driving home and at the first red light, I see he sent a text saying, “Well that was super awkward. Don’t think I’d ever put myself through that again!” I get home and write back asking what he’s talking about. He proceeds to inform me that I was faking being sick to get out of the date. After my insisting that wasn’t the case, he asks if I want to go out again. I turned him down saying after this interaction and being accused of lying, I’ve simply lost interest.

    • janee says...

      Your first story reminds me of a horrible first/last date with a man who invited me out for an ocean ride on his jet ski. I’m actually fairly terrified of the open ocean, but I can do offshore because I love the coastline from that perspective. I began to worry when he jetted straight out until we were about two miles offshore. I barely knew this man and realized I’ve made a bad decision as I was now alone with him on a tiny jet ski in the middle of nowhere. But it gets worse. He said he always jets out two miles to drop a fishing line off the back of his jet ski – which he proceeded to do. I am a seriously long-term vegan but neglected to mention that. Second big mistake. He almost immediately catches an enormous mahi – then takes out an aluminum baseball bat and begins violently bashing the head to kill it.
      Paralyzing horror does not describe my response. Then he asks me to drive the jet ski back because he has to hold the fish as it’s too big for his compartment. Two miles on open ocean waves is a long time to keep my tiny hands in a grip on a man-sized throttle. My forearms were agonizingly sore for TWO WEEKS. I decided it was my own fault for not speaking up about being vegan and banning the fishing idea right up front. Ugh.

    • s says...

      i had a guy accuse me of lying about not feeling well either! long story short, i had plans with a guy in the afternoon. that morning, i was on a 17 mile marathon training run and having explosive diarrhea (it was a miserable run), so i texted him and said i wasn’t feeling well and would let him know. he accused me of being hungover. i was furious and wanted to provide him the disgusting details, but didn’t.

      (in the end, it was an awful date. surprising?)

  66. Sam says...

    I went to a movie for a first date. To my unending horror, he talked loudly during the trailers and first scenes, confused as to why I wasn’t eagerly responding to his comments. And then he proceeded to sing every song in the movie. It was office Christmas party. I made a hasty exit after, claiming to be exhausted when he suggested drinks. I unmatched him, and he found me on Facebook to send me 3 messages to let me know there had been some glitch and we were no longer connected.

  67. Silvia says...

    A few years ago a really good friend of mine decided to set me up with another of her friend’s best friend. We went on a date. He picked me up, and we went to a restaurant near by. After 10 minutes of awkward initial introductions I tells me he is having an affair with his best friend’s wife. My only response was a “oh really? Wow…” (yes I know, what was I thinking). Fast forward to 15 minutes later (after knowing all the information that I reeeeeaaaally didn’t want to know) he tells me “but look me and you we can still happen because I am polyamorous” – Lucky me, ah? He went to the bathroom and I though “This is my cue, I should leave”, but out of respect for my friend (the one that set us up) I stayed. Eventually I gained to courage to tell him that even though I appreciate all the sharing me an him would never happen. As we parted ways (already on the sidewalk) he tells me “ok since this is never gonna happen, wanna go to my place and have sex?” I awkwardly smiled and told him “thank you so much but no” (why I said thank you I will never know)….

    • liz says...

      omg gross!

  68. Anonymous says...

    My first date was one of the most awkward moments of my life. I was asked if I would like to see a movie by a nice boy in my English class. I was a sophomore in high school and fairly naive. I wanted to see the movie and knew a friend did as well. I asked if my friend could come. He responded sure, we could meet with some of his friends for ice cream after the movies.
    Fast forward- my friend, a nice boy who I occasionally hung out showed up at my house with flowers. Minutes later English class boy also shows up with flowers and proceeds to drive us to the movies where I sat completely unaware of any awkwardness.
    It wasn’t until we reached the ice cream parlor and his friends began laughing hysterically that things clicked. I was on my first date, with two guys!!!
    I didn’t have the courage to date again for years.

    • Liz says...

      I had forgotten about this!!! Such a good headline, can’t even believe it

  69. A Martin says...

    I had so much fun in my single days in San Francisco. My friends and I were at a bar and the Red Sox won the World Series. It was pandemonium and I had too much to drink. So did this tall red-headed guy I ended up talking to all night. We stumbled to the next bar and man…I’m not sure exactly why I started crying…but I was. I cringe and laugh just thinking about this…!! I lived only a few blocks away and he insisted on walking me home. We had this passionate disagreement all the way to my place where I’m just crying about who knows what. The next morning, I woke up with a gnarly hangover and his sunglasses in my purse.

    Fast forward a few months and I’m on the express bus from the Marina to Downtown…wearing this guy’s sunglasses because they actually looked pretty good on me so they became my go-to sunglasses….As I’m zoning out, listening to my I-Pod (it was in 2007ish), he walked into the bus. Ahhhh!! I quickly removed the sunglasses, shoved them in my purse, and shrunk myself so small. In hindsight, it was pretty cool that my crying that night didn’t scare him! I had NEVER done that before and I’m pretty sure if would have freaked any dude out…except the mystery red head in SF whose sunglasses I still have.

  70. Gemma says...

    For some reason, when out for dinner in a public place, my husband and I often start pretending we’re on a horrible tinder date. We think of all possible ways to make the conversation cringier and it never ceases to be a good time. Highly recommend.

    • Marianne says...

      I love this! I’ve been on some absolutely horrible, cringy Tinder dates but pretending to be on an awkward date with you husband is hilarious.

    • Anne Knapp says...

      Oooh, funny! I’ll have to try this!

  71. Tasha says...

    It’s horrifying how much women put up with just to soothe men’s egos. Going on dates they don’t want, listening to men talk and talk with no regard to their opinions, accepting physical touch they don’t want….. Wow.

    • AN says...

      So much this. ^ It actually physically hurts my insides reading so many of these experiences. Why, why do we see ourselves as/act like second-class citizens who deserve so little?

    • Christie says...

      Agree! I would have just explained the mistake and offered a polite apology and left.

    • Caroline says...

      So true. I was wondering why she didn’t make an excuse and get out of there ASAP.

    • Joanna Goddard says...

      we were actually chatting about this in the office today. she said she would have left, if it happened nowadays, but it was harder when she was younger. i think we’re all learning as we go!

    • janee says...

      because women are generally nurturer’s by nature and the dark side of that is that until we master it we often err by extending the benefit of doubt inappropriately. unconscious men take advantage of that. agree we all learn as we go and that’s why women need to share their stories with each other!

    • Nora says...

      I was in a relationship with a frightening and manipulative guy for 1,5 years based on being nice to him and not knowing how to get out of it. Why do we do this? He basically didn’t leave after a date, just fell asleep on my sofa and sort of stayed.

  72. Katie says...

    Oh my goodness, so many awkward dates, accidental dates, unsolicited dates! The stories! Some of them make me want to hug my younger self in the tightest squeeze and tell her everything is going to be okay (the creepy, much older boss who sat WAY too close at your 1:1 “work dinner” while traveling in an unknown city). Others make me want to shake her (you took DRUGS with a STRANGER on a FIRST DATE?!). And others have made such hilarious fodder for brunch with my girlfriends that I beam with pride for her when I think back on them (the artist who invited you to his studio full of bags of bird poop he used to fertilize his plants). To all those who are dating, Godspeed!

  73. B says...

    did you ever go on the real-Rob date?? :)

  74. Jessica says...

    These stories are awesome! Almost woke up my newborn laughing so hard.
    I once went on a date with a guy oversees. We agreed to meet at a trendy downtown street with nightlife. When the date was over, he offered to share a cab home. He then proceeded to instruct the cab to drop him off first since he was closer to our date location than I was. Not so great but not terrible either). When we got to his place, he slipped out, went to the driver and spoke over something quietly. He came back to me in the he back seat and said that he had paid the driver for his portion of the ride and had worked out a good deal for me to pay the driver for my portion of the ride. I saw their 90% shocked and 10% thankful.