What is your most awkward / embarrassing dating story?

About 4 months ago I went on a date with someone I met on OkCupid, she was three years older (25) and I was definitely punching above my weight... so nerves were through the roof. We went to a bar but it was really nice and the dress code was smart casual. I'm there 45 minutes early, you know, getting some dutch courage... next thing you know she comes in wearing a 1990's like blue and pink shell suit like this.
What is your most awkward / embarrassing dating story?
She is a completely different person (looks the same but personality, not so much) than I was talking to online.

Anyway, conersation is terrible but I'm staying to be courteous. We order food... and then she starts breaking the crusts off of her pizza and flinging them at me whilst yelling "fire in the hole".

I wrapped it up 10 minutes after we finished eating and we never spoke again.


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Most Helpful Girl

  • This guy had been trying to get me to go out with him since senior year of high school (3 years.) i finally decided to go out with him out of pity. Thinking, "hey maybe he's a nice guy and isn't absolutely insane) We went to a really fancy restaurant for our the first date, and he brought a wedding ring. :)

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    • @guy532 i believe her because trust me there are lots of weirdos in this big world.

    • I am waiting for the update where you say that you are engaged and will marry him next month.

Most Helpful Guy

  • Very long story short

    I was given a pity date. She invited her friend who was also trying to get out of a bad date to join us. She knew the bartender and made sure she got me really drunk. We went to the dance floor and I was so drunk I didn't even notice the girls ditched us and I was basically dancing with the dude her friend ditched. I left the bar, wandered around downtown looking for a cab. Found one, got it to drop me off 10 blocks from my place (im pretty sure she put something in my drink too...) because it was nice outside. I lay down in a field to look at the stars. I pass out. I wake up the next morning to the sound of kids playing - I passed out in a soccer field on a school day. I still have the memories of the supervisors in their reflective vests staring at me and a few kids in the distance looking as I stumble my way to my house a couple more blocks away.

    Worst date ever

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What Girls Said 8

  • I went out with a guy who worked as a temp at the company where I myself work. We were supposed to leave right from work, but he had to sit a guy's car first and he told me to wait. Turns out he was buying pot. From there, we went to get coffee, and instead of just asking me to pay, he diverged from the line and ignored the cashier until I offered to pay. He spent the entire day bitching about his life, made me walk him four blocks from the coffee shop when I said I didn't want to because it would be getting dark soon, and then bombarded me with messages begging to go out with me again.

    I broke it off face to face with him and he wasn't accepting no for an answer. He kept saying we needed to "take a break and try again." I was straight up and said no, and he got fired a week later for having a shitty attitude at work.

    Good times.

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  • Hahahaha your story made me laugh! Mine won't compare, but when my boyfriend and I first started dating (a few months into the relationship) I felt nauseous. We were sleeping but I couldn't go back to sleep. Now I have a fear of throwing up and try to chime "I won't throw up" to get it out of my head. I have passed out when I've seen other people throw up, so it can be scary. But I didn't want him to know about my irrational fear, so when I continued to feel nauseous, I decided it would be a good idea to go to the kitchen and get ginger ale. Ginger ale always helps. Well.. I didn't even make it to the fridge. I passed out in the middle of the kitchen floor and my head was against the wall and the stove. He woke up when he heard the "boom" and was screaming when he saw me. He thought I broke my neck with the way I landed. Once I opened my eyes I saw that I was on the kitchen floor and knew it was bad. Apparently I wasn't responding for "a min that felt like an hr". I scared the shit out of him.

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  • Hahaha.. poor you! I think mine most embarrassing date ever was when the guy I was supposed to meet ( he was 27 that time ) came at the first and last date we had with both of his parents.

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    • *facepalm* I would probably have made an excuse to leave asap. That's soooo weird.

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    • @guy532 27 years old at that time

    • Really? Couldn't he even at the very least have taken the bus, what an idiot lol

  • LOOOOOOOOOOL

    That sounds like someone's idea of a bad prank
    I recently went out on a date with a guy who would clearly be abusive down the line, randomly started calling me rude names out of nowhere and tried to grab me. Ran outta there asap

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  • Met a guy to 'hang out and have beers'. Yea, he hijacked it and turned it into a full fledged four course date, talking about all the failed relationships of his life and ended up laying in geese shit. Great time.

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  • It is waaaaaaay too embarrasing to tell.

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  • (laughing)
    ... where to start x 1000000000000000000000000000000

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  • What a funny story.

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What Guys Said 18

  • Wow dude that's so weird haha, funny and weird. At least you got a good story out of it.

    My worst date is really not even that bad. I asked a girl out and she said yes. I wanted to take her out to dinner and stuff (I had everything set for a wonderful date), she tells me it's better if we just meet 20min before her work at the mall for some coffee. I thought the date went well. She told me she wanted to see me again. I texted her and she never replied back. I'm still mad at her for wasting my time, not only did she not give me a fair shot by changing the orginal great date I set up for a crappy 20min coffee date at freaking mall like we're 14 years old with me at 7am when I lived 30min away, but for also that even though I STILL managed to pull through and actually give her a good freaking time and she lied to my face about wanting to see me again, I didn't even bring up the second date before the date was over, she did. Honestly who does that?

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    • It's bizarre that some girls do that, they can still polite and say "it was nice meeting you" "I enjoyed this" or whatever they don't need to actually say they want to meet up again.

  • not super embarrassing but I went out with a girl once and thought she resembled a celebrity

    so I told her you know you look like Allison Janney... which isn't really an insult but probably not all that flattering for most women to hear
    static.guim.co.uk/.../Allison-Janney-014.jpg

    I really meant to say she looked like Laura Linney though
    ia.media-imdb.com/.../...317_CR7,0,214,317_AL_.jpg

    didn't realize it til the next day that I'd confused the names

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  • What a dumb fucking bitch, this story pisses me off, I would ask her out again, make like you'll pay for everything, say excuse me, walk out and leave her with the bill

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  • I tried to build gingerbread houses with a girl. . . in July. She made some sly comment about the date being in the wrong season, and the date went downhill from there. Now it's a wintertime date.

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  • Haha ok cupid is fucking awesome.

    What's dutch courage?

    I don't have any good date stories except I got drunk on a second date and the girl drove me home and basically raped me in her car. I couldn't even get it up all the way but she got on top of me and after like 15 min of that I got out and puked.

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    • Dutch courage is the confidence that you gain from drinking alcohol.

    • That's basically what my context clues tole me but I've never heard it called that before. Did she really say "fire in the hole" and did she try and do it to give you a boner?

    • She said it three or four times and I don't know what her motives were but she certainly didn't give me a boner!

  • There was this girl I met on tinder. We talked for 3 days and decided to hook up. Unfortunately for her I had masturbated 3 times in one day to the nudes she sent me. So we she drove to my workplace. We got in the car and i got semi hard. She tried putting a condom on but it hurt me and I couldn't get hard after that. So I just did cunnilingus.
    Usually I joke around but this is true.

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  • here's awkward for ya: i was at a joint birthday party. a friend and a girl he knew were celebrating w/ a joint birthday party in a cheap LA ballroom. my friends and i were drunk before we knew it (open bar).

    next thing I knew, i was outside sitting on a step throwing up on my own shoes. i felt miserable. by this point i couldn't even lift my head, eyes half shut, staring at my feet, and blowing chunks every 2 min...

    next thing i know i hear this voice of a girl, asking if i was alright. she came and sat next to me and comforted me by rubbing my back until the cab arrived. i instantly fell in love without even seeing what she looked like.

    the next day, i asked my friend who was that girl, and it was the birthday girl (so i felt even more special). asked him to relay my # to her to text me (dunno if he did), but never heard from her, or seen what she looks like to this day.

    the end --------------

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  • When I was 16, I looked like I was 22. I was dating a girl who was 19 and after the date we went back to her place. It was going good until her Mom came home. There was some yelling going on and I was just like "I'll call you" trying to get out of the place half naked with a hard on. Anyways I make it to the front door about to leave and the Mom yells "Halt, young man!" I turn around expecting a lecture but she saw I couldn't really zip up yet. She grabs it and whispered, "Come back tomorrow at 2pm." I freaked the fuck out and never went back or talked to her daughter again.

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  • Never really had an awkward date, but your story is super funny

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  • I've never had a date.

    How much more embarrassing can you get?

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  • i smoke weeds too much before date , i am about to meet her for first time
    you can imagine what happened

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  • A+ for effort lol

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  • Omg hahaha xD Well i dont have a story of the same kind because i have never dated.

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  • I would call this awkward and my fastest lay. Matched on tinder, talked for 1 week. Decided to meet her but the weather was so shitty I just told her lets chill at your place and watch a film. I suggest Get Hard with Kevin hart in it. Not 5-10 mins since I walked in her place, I was already laying kisses on her. But then my dick won't stop going soft. Everytime I tried putting a condom, it woud go soft. Shit was so embarassing. Never in my life had this happened to me. She said " Dont be so hard on yourself". Im like "WTF. Dont give me that shit, Im basically useless if my dick can't stay hard". We tried 3 times but to no avail. Finally, I just said "Fuck it". I had my 10 second glory in missionary position lmao

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  • She seems like a fun girl tbh. I would've loved her I bet. How on earth did she get in dressed like that though?

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  • Your dad walked in when I was balls deep in your mom

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  • I had a first date with a woman who could probably drink me under the table, took me back to her place, gave me a blow job and prostate massage at the same time, I fell asleep, and when I woke up, $50 was missing from my wallet.

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  • Back in the day I was living in L. A. and in a band. One of the members (The most outgoing) set up a triple date with me, him and a third band mate. The date setter-upper had gone to USC and knew this girl who supplied two friends going to USC for the occasion. Long story short, his date (not the girl he knew) was tall, as he had been a basketball player (6'7"), and mine was about my height (5'7"). He took an instant liking to my date and ordered her and me to split up so he could be with her, and I wound up talking in the back of this music van (no seats mind you) with a woman 6'1". Of course my generosity of spirit wouldn't allow me to break up the band over that, and I actually felt sorry for the tall woman, as personally I had no vested interest in any of the women, it wasn't like I knew them before and actually liked the girl my height. He was a pushy arrogant "alpha" who later dated a Playboy model, and eventually he quit the band.

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