People's Most Embarrassing Dates

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  • 01
    Font - RosiePugmire • 18h It was one of those setups where my mom and his mom were friends and they were like, "our two nerdy, intensely introverted loner kids should date!" Unfortunately that was the literal entirety of what we had in common, so. Bonus detail: we went to a theater that was showing "The Big Sleep." He fell asleep. 6 Reply 1 1.4k 3
  • 02
    Font - polyesterbrown · 19h 1991: Finally asked out a really gorgeous coworker, she said yes. Take her to a party and we rode with friends there. Once we're there she proceeds to get on her face, then spends the evening talking and flirting with another guy there that I didn't know. Evening ends and we ride with friends back to our vehicles, dude comes along too and they both make out with each other next to me in the back seat. My only revenge is that I told everyone at work how the date went.
  • 03
    Font - ghOstmanX • 19h 3 Awards This was embarrassing in the moment, but it worked out. It was a 2nd date, but it was also Valentine's day, so I decided to get her flowers, a card that plays music, and some chocolates. It was freezing cold, but I didn't have anywhere to keep them besides my car. I took the chance the flowers might die. We had a nice date, and when we get back to my car I got them out. Oh those flowers were DEAD. "Ah well...". She opened the card, and the sound chip just went bbb
  • 04
    Rectangle - danidoodle · 16h On my first date (I was 14) we were walking in the park and I very animatedly and loudly hissed at a goose. Sorry Alex, that was really weird. I still cringe at this from time to time. G Reply 4 153 3 ...
  • 05
    Font - garlicroastedpotato · 14h It was all my fault. My first date with this girl we went to a restaurant called "Duck Duck Goose" that promised duck and goose based tappas style dishes. We ordered duck meatballs and duck poutine. The duck meatballs had a sauce with it... which just ended up being duck grease. The poutine curds were also made of duck grease and disgusting. After eating just one of the three meatballs she confided in me that she hates duck... and that I also realized... I hated
  • 06
    Rectangle - randomredittor21 • 13h 3 2 Awards He took off his shirt at outback until the waitress asked him to put it back on then stood in the parking lot loudly (and badly) rapping to his own music. Shoutout to Eli G Reply 4 804 3 ...
  • 07
    Font - Lil_Sousa • 14h 3 Awards Girl and I made plans to meet at an outdoor mall and see a movie, this was back in middle school so my mom had to drive me in about an hour's worth of traffic, and she cancels 15 minutes out. I felt so bad for my mom driving me all the way there already so I simply pretended like she hadn't canceled, my mom dropped me off, and I watched a movie by myself. Almost cried but I kept it together. But I mean the movie was good at least. 6 Reply 1 845 + ...
  • 08
    Font - tmobley87 · 15h My George Costansa moment. Went out on a date with a girl going to college at a neighboring town. Went to dinner and what have you. When I went to take her back to her college apartment, we sat and chatted in my truck for a few minutes. Then she said "my roommates gone, do you want to come up for coffee?" My response was "no, I don't like coffee". She gave me a strange look , we said our goodbyes and I left. I was half way home when it hit me. I wish I could say I'm just g
  • 09
    Font - serious_rbf · 20h I invited my bf at the time over to watch movies in my basement. Instead my grandmother sat in between us and we watched the game show channel. For 3 hours And it wasn't even like she was trying to prevent us from doing stuff. She just wanted to hang out with us. G Reply 1 1.1k
  • 10
    Font - Love-that-dog • 18h We had an mediocre date, then walked to her apartment. On the way, she took a phone call about a couch she was buying. This call continues for the next few hours (!!!) of the date. To entertain me she put on a show on Netflix- You. This show is about a stalker, and is not really good first date material. At the end she said, resigned, "There isn't going to be a second date, is there?" And I agreed there would not be. G Reply 4 527 ...

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