What’s Your Most Awkward Date Story?

Oh ha ha!
His car… it his mums?

Ok here is mine. So I knew this guy and he really liked me. He gets a bunch of tickets to a play and invites a lot of people. He is in charge of tickets and he sits down next to me. I had no idea what was going on right away. He kept trying to hold my hand. I kept declining it. Finally got to intermission and after I came back from the bathroom he grabbed my glasses like he wanted me to fight him for them back. I refused to acknowledge that any of this was going on. I left and that was that.

Well here’s my contribution ..

On my first year of college i got really obsessed with this guy, dylan , and i kept looking /staring at him whenever possible . And then one day we were sitting next to each other during a conference and as i was running out of papers he kindly offered me some of his .i couldn’t even say a word. I was mortified . I smiled and blushed and wanted to disappear .A few months later as i was convinced that i would never have the courage to approach him , i spent a whole week trying to write him a fb message . I finally got that perfectly engineered message sent and i crossed my fingers for good results.
in my message i told him that i had some extra college books to offer him -for free .i said that i just wanted to repay the favor , so i gave him my address and my telephone number so that we could arrange a meeting .
Two weeks later ( two stressful , desperate weeks dare i say ) he reached out to me .he basically said that he sas very surprised of my offer yet very touched .he said that i was very kind and that he would be more than happy to get the books . I was extremely excited to read his message . I read it more than you could ever imagine .
at that point i was waiting for him to reach out for an eventual meeting . The next day i checked my fb hoping for a message and … Surprise …. He had changed his profile picture . In the new profile he was there , holding hands with a girl in paris . Probably his girlfriend.I guess his message was clear . Needless to say i never reached out to him ever again .

Lesson learned . You could never buy love .

Long story short: I got lost in the woods at night with a guy on a first date once.

It was a friend of a friend, so there was already a certain amount of familiarity and trust, and we met to take a stroll in the small forest next to the city on a hot summer’s evening. It was supposed to be a short walk because he had injured his foot a week earlier and walked with a limp. We hit it off and made a game out of picking the way to go at the crossways based on our “scout intuition”. Needless to say, this intuition was absolutely nonexistent (none of us had ever been a scout) but we still trusted in it and refused to check our GPS until there was no signal to actually use it. We got totally lost in the woods and it got dark. I had talked about being afraid in dark forests earlier and was trying to not freak out in front of this guy whose company I actually enjoyed a lot.
The summer night became quite cold, I wanted to use a toilet, and he was probably having a lot a pain limping all night long. But we joked about being the very worst scout team of the world all the way back. Instead of the short walk we had intended originally, we spent 6 hours together on our first meeting until we had found our way back to where we had parked our bikes. It was after midnight then. When I finally arrived at home I realized I had various messages from my best friend and flatmates worrying when I would come home or half-joking whether the limping guy had already buried me somewhere.
The most awkward part of this situation was having to tell them “we got totally lost in the forest” as the reason.
For a while after, I lost all credit of being a human being capable of navigation. I was not even trusted by my best friend to find my way to the local supermarket.

I was on a tinder date with a guy and the conversation was going better than I had expected. We talked about all different things, including family (mine all lives close by so they’re a big part of my life). About an hour and a half into our conversation, I saw a wave of terror cross his face and he asked me if my sister was Michelle, and I said yes. He then told me they had dated!! I was speechless, and didn’t really know what to think, but since we were having such a good conversation, I wanted to continue the date. We kissed at the end of the night and all I could think about was him kissing my sister. Needless to say there was no second date!

My husband and I dated long distance in college, but by his second year, most people knew he had a girlfriend (it was a small school, he was in a fraternity). We both had lots of male and female friends, so he didn’t think it was unusual when a woman in one of his classes asked him to get lunch together until she insisted on buying his lunch. He decided not to overthink it, and said he would get the next one. As they sat down, she said ” wow, you’re confident, you already think you’ll get a second date.” My husband choked on his food a bit, and awkwardly (but kindly) explained to the woman that he was in a relationship, and had been unaware that this was a date. She started crying, saying that it was the first time she had asked someone out without looking them up on the internet, because she wanted a more “organic” experience. My husband calmed her down, and insisted they finish their meal so they could at least be friends. He paid her back for his lunch, and went out of his way to be nice the rest of the semester. A few months later, we were on campus grabbing snacks before a movie marathon with his friends, when she approached me and apologized for making my boyfriend into an “unwilling cheater” and hoped I forgave him. I made the comment that he didn’t really cheat on me, and I actually thought the situation was a little funny. She was super nice about it, and actually attended our wedding!

Not the worst but one of the spookiest dates. Around Halloween too!
Met online, agreed to grab coffee.
I walk in, he sits by the bar. First thing I notice – jeans are the same color, mine are ripped on the right knee and his on the left (we sit next to each other). As I look up I realize he’s wearing a t-shirt and a black leather jacket. Just like me. Looking closer at his face I notice that he has a mole on his left cheek (I have one on the right). AND WE ARE EXTREMELY ALIKE. Except his hair is short and darker. But the faces are almost identical. We laugh it off but it is somewhat disturbing. Have a pretty good conversation but this whole situation is just so weird.
We stayed friends.
I looked at his online pics after the date and couldn’t believe I didn’t see it in the first place. Even showed it to my mom- she was joking about my lost twin.
The best part: he texted “You are gorgeous” after the date and I thought that it’s the funniest thing to compliment someone who looks like you so much.

Went on a date with a girl I met at a dance club. We met up at a bar, had a few drinks…she had a lot more than me and was soon pretty drunk. We decided to head to a new spot. On the way, she insisted she had to stop somewhere on the street to pee. We were 2 blocks away from the next bar so I told her to wait, but she decided that was too far and went to an alley. Instead of hiding behind a dumpster, she proceeded to drop her pants 3 feet from the sidewalk in full view and made me hold her hand while she peed. I was obvi done with the date then, but worried about leaving her alone and she refused to go home. We went to the next bar and had water while she tried to pressure me to have sex in the bathroom. After that I got her a ride home and that was the last we saw of each other.

I’d gone out on one date so far with this guy I found on OkCupid; I’ll call him Joe. I was recently out of college, recently single, and happy to meet just about anyone for the chance at a connection (or, barring that, at least a fun hook-up). For our second date, Joe invited me to a party at his house. I was having a great time, feeling like I was connecting well with his friends and even exchanging numbers with a couple of the women there, making plans for future hangouts. At some point he invited me to “see his M.C. Escher book” and I gamely went along with the world’s worst pick-up line, following him downstairs to his bedroom. He did show me the book, and then — despite having decided I wasn’t super into him — I somehow allowed him to make out with me. Joe undressed me, then asked me to get up and twirl for him so he could “see me.” I can’t believe that I actually did it, and that he had the gall to look unimpressed! He did go down on me after that; he wasn’t great at it and I faked some moans of ecstasy so he would think his work was done. Joe mentioned that he had “whiskey dick” but could be ready in a few minutes, and I said, “Oh, we’re not having sex.” He checked his phone and casually told me, “My girlfriend is coming over soon, so you should probably get dressed and go.” It was the first he had mentioned her. I played it cool, put my clothes on and went back upstairs, where the people I had hoped to befriend said they had heard us having sex. Mortified, I drove home.

I didn’t realize I’d left a necklace in Joe’s bedroom — a tight string of garnet beads that my mother had bought me my first year of college — until Joe messaged me to apologize. Evidently his girlfriend had come over, discovered the necklace in his bedroom, and flown into a rage and ripped it apart, scattering the beads everywhere. He offered to replace it and I accepted, but a few days later received a message from his girlfriend, who also apologized and said she would pay for the necklace. I politely declined, saying I preferred that Joe handle it since he was effectively at fault for the whole thing and I didn’t know her. Joe messaged me again, said I was clearly “just trying to get revenge” and that I would never get a replacement for the necklace and to stop messaging him. I was so gobsmacked that I sat there staring at my screen for a moment and then burst into tears.

I did end up making friends with the two women I met at his party and so ended up hearing about Joe a lot after that (and how sorry he was and how I should give him a second chance after he broke up with his girlfriend), and then I dated his girlfriend’s ex by accident, and then I invited Joe to a 1920s party along with two other men that I was dating, and then I never talked to him again after that.

I’d just moved to Omaha from L.A. 1988. I don’t recall where I met the guy. I said yes to a date for Italian food, but asked to meet at the restaurant. It turned out to be a steak house. Just as our waiter walked away, while I was still trying to reckon with the revelation that my steak was served with a tiny side bowl of iceberg lettuce and a tiny bowl of room temperature spaghetti, he leaned across the table as if to say something important, looked me in the eye, and said, “I robbed this place once”.

I’ve been on so many weird/awkward dates with questionable men that my friends told me I needed to write about it…so, I recently started an Instagram account of just that. I think maybe I’m delusional for thinking I will meet “the one” on a dating app (disclaimer: I met my ex-husband on Tinder…so that worked out well lol). If you want some laughs, my IG handle is DatingInDelusion. xx

I decided to try online dating because it was new in the early 2000s. I was living paycheck to paycheck at the time and on that day, my account balance was abysmally low. I agreed to meet my date at a trendy sushi restaurant that just opened; he insisted on paying. I had taken a cab from my city apartment and had just enough cash for the cab ride home. I met the guy, a “musician”; the date was going fine, not great, not terrible. We both ordered a drink and a roll of sushi and had decent conversation. Towards the end of the night, I went to the ladies’ room, and he said he would pay. When I came back, he was not there, yet the bill (over $100) was sitting at our table – unpaid! I literally could not cover the check myself, so I left my cab fare as a tip and walked out, red hot with anger and embarrassment. It was going to be a 45-60 minute walk home in the cold, dark, and potentially dangerous city. Fortunately, a taxi saw me and picked me up. I told him what had happened, tearfully, and he took me home for free. I never went on another date without being able to afford the whole thing myself (including transportation).

I went on a Tinder date a few years ago with a handsome, extremely religious man, lunch at a little Greek restaurant. About 10 minutes in, I told him I wasn’t religious and I hoped we could still eat our Greek food in peace (mostly joking, all in good fun). He replied, very seriously, with “It’s okay, but it just means we can’t get married. I want a wife who shares the same values as me.”
I ate my spanakopita in silence as he talked about what he looks for in a wife and then I made up a story about having to suddenly leave and I left.
Marriage doesn’t scare me, but the prospect of it on the first date does, and then to be DENIED it… what a rollercoaster.

My worst date with from Tinder… he seemed normal, was a lawyer, seemed smart and witty. We chat a bit and agree to a date. First off, he ends up arriving more than an hour late and shows up notably drunk from a child’s daytime birthday party (??). Then he proceeds to tell me that he figured out my last name and where I worked and that he used to date my co-worker – who I very much like and is an amazing woman. He then let me know that they didn’t work out because she was too prude (again, sir, I told you she was my friend…). He THEN informed me that he requires sex every day and based on my face (of total shock and maybe confusion as to whether I was actually hearing what I was hearing – like this was 10 minutes into a first meeting), it didn’t seem like it was something I was willing to do (after arriving drunk and swearing, I decided that was never going to happen anyways). Then, to further elaborate, he let me know he’s not some total sex weirdo and that, in fact, “missionary every day is fine”. Like most other stories in the comments, I am embarrassed to say that I did end up staying for at least an hour more trying to figure out a graceful way to extricate myself. The waitress looked like she felt sorry for me. But “Missionary Every Day” became somewhat of a single woman rallying cry among my girlfriends. Also, based on texts from the next day, he thought the date went super well… I guess he decided maybe I could in fact handle missionary every day…

I gave up dating, way too many crazies.

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

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.

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!!!

Probably the best comment (and story).

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!

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.

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.

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.

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!

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.