Most embarrassing first date stories?

Tell me your most embarrassing first date story tell me your age, and where you were. (:


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Most Helpful Guy

  • I was on one of the popular dating websites, and women were not responding to my emails, or "winks" as the website put it. then after 2 years of silence, I recieved an email.

    we went back and forth a bit, she told me she was and I quote "slightly full figured"

    I am not the ideal weight myself so I figured its been 2 years, beggars can't be choosers.

    so I agreed to meet.

    the eve came, I went to the bar we agreed at, and standing at the door was this Obease woman, 410 lbs at least. she was walking like a penquin back and forth and heavy breathin. I figured it can't be her, so I started to walk by, and she called me by name.

    well, I musta gone pale, because there was clearly no blood in the brain when my mouth said "HOLY COW" without thinking.

    well, that was a record for shortest date.

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    • Lmao thanks for sharing. (:

    • Not your fault lol

    • Omg that is awful. Drives me crazy that people blatantly misrepresent themselves online and then get shocked when the first date does not work out.

What Guys Said 4

  • im 17 and we were partaking in illegal activities such as getting high mind you neither of us are drugies. we both use it very very sparingly and it was just me and her. anyway so my car alarm went off and we were in the parking lot of the movie theater. I got outa the car and she started to freak out because she thought I was ditching her and running. haha. but the only way to shut off my alarm...because its messed up...is to unlock the passenger side door with the key. it was kinda embaressing that not only my car alarm went off...for about 10 minuits but she also thought id ditch her because I was scared. hahaha

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  • I am a 30 year-old guy and this story happened 5 years ago. The most embarrassing date I've ever been on was a first date with this cute girl from my apartment complex. My ex-girlfriend saw us on our date at a restaurant and came over to the table to try to convince my date not to like me. She told her that I wear thong panties and asked her, "do you want to date a guy that wears panties and a skirt?"

    OK, the truth is that I do wear thong panties...pretty much everyday. That ex-girlfriend was the one who started me wearing panties because she said that I should obey her two rules of underwear; 1) go cute and 2) go skimpy. She actually threw away all of my guys undies (bikini) and replaced them with thong panties like 3 years earlier. Honestly, those panties are the most comfortable undies I've ever worn. Anyway, she started me wearing panties and was telling my date all about it. The fact that I wear panties, and thongs at that, is not something I would reveal on a first date. And the skirt comment was from a couple of halloween costume parties that we had went to together. I went as a cheerleader to those parties and, or course, wore a tiny skirt. But my ex-g/f loved that I went as a cheerleader when we were together.

    So...back to the date. She tells her these things and my date just smiles nervously. I was dumbfounded and just sat there with my mouth hanging wide open. It was so embarrassing. I then stand up to escort my ex-g/f away from our table and my ex-g/f twists my arm behind my back and pushes me down on all fours right in the restaurant. Then she sits on my shoulders and quickly reaches into the back of my jeans and gives me a wedgie. I was wearing a pink lace thong and she showed it to everyone. I was so shocked that I did not move. She just held my thong panty in wedgie position and said, "see, aren't those nice panties?" I could hear my date, and many others around us, starting to laugh. My ex-g/f stood up and marched off and I stood up and blushed. My date said, "you might wanna go the bathroom and straighten out that pink t-back." I nodded my head and went to the bathroom. When I came out of the bathroom, the waitress smiled at me and told me that my date was waiting outside for me. I walked out of the restaurant and my date said that she wanted to go home. She said, "I don't think we'll be going out again." When I dropped her off, she said, "thanks for an entertaining date and a very interesting story." I asked her if she'd be willing to keep the fact that I wear panties a secret. She said, "not likely, I'll probably tell as many people as possible." Then she closed the car door and walked off.

    That was the most embarrassing date I've ever had

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  • well... this probly doesn't count but it could have been an embarrassing first date. I asked this girl out on a date thinking she was like 19 I'm 24 she said yes. than we were talking a few days later (before the date) and she asked how old I was and than I asked her and she said well let's just say she was way younger than I thought (far below the underage limit) needless to say we called off the date but if we made our or anything and someone came up to us knowing our real ages it would have been realy embarrassing.

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    • How old was she anyway lol? not like you can get caught on here... this could be a fake story for all we know :P

    • Well she was 14. she looked 18 or 19 to me because she's like 5'6. she must have thought I was younger too because she said yes. I'm 5'1 so I look pritty young for my age. (non smoker)

      we didn't go out after we found out how old each other were.

  • I'm going to have to say that the most embarassing story is when I was about to kiss my date goodnight at her door and she barfed all over me.

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What Girls Said 5

  • A guy asked me out for a date and he suggested we go to a local seafood restaurant. I think I had just been there recently and I wasn't feeling it so I told him that I wasn't interested in seafood and he offered another suggestion.

    Well, we went to the other restaurant and I did not even think about it and I ordered, guess what, seafood. After I placed my order I felt embarrassed and didn't really know how to play it off and, well, that was our last date.

    I was in my early 20's and just did not have the social graces or skills to recover from something like that. Since then I have a rule that whatever the guy suggests I accept, and that it is a part of learning about him.

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    • Lol. I think this is a good lesson :)

    • I have been dating again recently and 2 guys have asked me out to a chain restaurant that my girlfriends tease me as being the kind of place you go on a first date when you are in High School, lol. But, I do not not miss a beat when accepting the invite.

  • I was 17 at a restuarant with my ex and it was our first date. I was so nervous that I was very shakey with my hands. I dropped my fork and I almost tipped over my plate of food. I couldn't stop giggling and he was looking at me like I was on drugs or something. Then finally at the end of dinner I got up from the table and I took the table cloth with me causing to spill soda and food left on the table all over my date. It was very embarrassing. Too bad he didn't ever talk to me again after that. Would have saved me a lot of trouble later on in the relationship lol.

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    • Hes a losser because you can't judge on things from the first time you go out. sh*ttt happen in life.

  • My current boyfriend and I had an embarassing re-encounter after we first met this past year in college. we lived in the same freshman building all year, and were on alright terms. One week, we sat together a couple of times at dinner just for company, no big deal-- and I got a message from him on Facebook asking if I'd go down for a movie with him and some friends. I was enthusiastic about it and brought popcorn and my roommate, thinking, "cool! We're becoming better friends!"

    Well, I showed up, and he stared at me with surprise. "Hi! What are you doing here?" I thought he was kidding. He wasn't. He thought he invited another girl who shares my first name but a totally different surname, not even close. "The blonde!" I was mortified and tried to leave, but he caught me and told me to stick around anyway. After that we always joked about it, and suddenly he began wanting to hang out more and more. :)

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  • I was 17 at the time. My best friend set me up to meet this guy at a house party thing and I agreed, cos if I didn't she would just keep hounding me, so might as well get it over with. (She still does now but I actually like the people now. Haha).

    Anyways, so I meet this guy and he's okay. Nice, a bit awkward, but I guess it was an awkward situation. Anyways, somehow the 4 of us (him, me, my friend and her boyfriend at the time) all ended up walking to Tescos, and while we were walking there I was just chatting with my friend, as you do. And this guy behind me kept whining and moaning that I wouldn't talk to him, I swear he was such a baby. So I let behind a little and started talking to him, and suprise suprise he didn't have anything to talk about. Great.

    Anyways. On the way back from Tescos we went past this pub, and this guy wouldn't let me cross the road like the other 2, so I was a bit like, wtf? He stops me and goes 'Pinky, I really really really like you, do you like me?' That kinda caught me off guard. I mean I'd only met him like 2 hours ago, how the hell could he say that so confidently? So I go 'Erm, sure.' Lol, I couldn't really think of what to say... To be honest I found him kinda annoying. Then he pulled me into a hug, and went in to kiss me I just thought to myself 'Oh poop, think quick' and dodged his face, ahaha. I'm so insensitive. I guess it was more embarassing for him than me. Though I still found it pretty embarassing too. The rest of the night he kept putting his arm round me and when he left he did this horrible beckoning thing that for some reason just made me want to scream.

    Even after the party the guy kept asking me out, and chatting with me on facebook and stuff. I did actually consider giving him a chance but whenever I talked to him all he would talk about was himself. He's a self centered jerk. (Don't worry I didn't lead him on, I told him I didn't want to go out with him. But even after that he kept whining about it and it p*ssed me off even more. Lol)

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  • i was 14 and it I guess it was a date. I was hanging out with this guy I liked and he had one of his geeky friends come along and his friend was staring at me the whole time and thought I was impressed by him because he knew how to steal stuff from a vending machine.

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