Most Embarrassing Ways People Messed Up Dates

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mattstaff
Apr 2, 2021 5:00 PM EDT

The world of dating can be a tough one. In this modern era we have all of these crazy dating apps available at our disposal, and those very apps can end up resulting in quite the ridiculous series of encounters with individuals that seemed sane enough on the surface level, but ended up showing up for the date, brandishing all the bright red flags. Hopefully these people's stories about their most embarrassing dates make you feel a bit better about your dates that erred on the side of disaster. 

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  • 01
    Font - mkramer4 · 3y I offered to pay for the bill.. she insisted to pay half. Didnt fight it, but only had a large bill so I pocketed her money and put my bill in. Anyway long story short I did the math wrong and stole 20 bucks from her. She sarcastically said "thank you" and I thought she was being sincere.. 3.7k ...
    via r/AskReddit
  • 02
    Rectangle - bacon_butter • 3y We order a small snack for our coffee and as it's arriving at the table he pulls out his Nokia phone. Trying to make a lighthearted joke I say "MAN that has got to be the oldest phone l've seen in a while". I really dug it in, trying to break that friendly wall. Well. Turns out it's not a Nokia. It was his insulin pump. 4 1.7k ...
    via r/AskReddit
  • 03
    Rectangle - Spidey16 · 3y I was 16 and on a movie date. Went to do that move where you stretch your arms then put it back down around her shoulder. Instead I just elbowed her in the face. 1 444 ...
    via r/AskReddit
  • 04
    Font - alphamale968 • 3y I flirted with a cute bank teller for weeks before working up the nerve to ask her out. Didn't realize she was super religious, invited her to a Mexican restaurant and ordered two margaritas. When she told me she doesn't drink I said "that's ok. These are uhh... these are both for me!" She told me I wasn't Christian enough for her and I agreed. And there I sat. Drinking two margaritas alone. 1 5.6k ...
    via r/AskReddit
  • 05
    Font - Fridgecrisis · 3y This was in high school. She invited me to her house to have dinner with her family, and I didn't know them very well yet. The conversation turned to names we thought were old-fashioned and ugly-sounding. We all threw out a few like Gertrude, Bertha, and Eugene, and then I said something like, "At least that one's not as bad as Deborah!" I used my ugly voice and everything. Her mom's name is Deborah. Her grandmother was also at the table with us. We've been married for a
    via r/AskReddit
  • 06
    Rectangle - -I_Am_The_GOAT- • 3y My friend took a girl to MACDONALDS(classy), and ordered food for himself, didn't even ask her if she was hungry. Then she was just watching him eat. There was that story which was told many times. 174
    via r/AskReddit
  • 07
    Rectangle - steeltornado • 3y I didn't know it was a date and bought my little sister to hang out with her too. 940 ...
    via r/AskReddit
  • 08
    Rectangle - kidkrush • 3y Called a girl named Rebecca "Rachel" multiple times. It wasn't in reference to anyone, she just looked like she'd be named Rachel. We're still friends I still call her "Rachel" sometimes just to tick her off. 565 ...
    via r/AskReddit
  • 09
    Smile - [deleted] · 3y She invited me up to her place, got us each a glass of wine and then took her pants off, at which point I assumed she was going to bed, said goodnight and left. 1 86 ...
    via r/AskReddit
  • 10
    Font - Oi_Kimchi · 3y I went on a date with a girl I met in an online chatroom to see King Kong at the cinema. I was in my young teens and the ending absolutely shattered me, even though I knew it was coming. I cried. Not a lot, but a couple tears. She noticed and asked incredulously if I was crying. I just nodded and without saying anything further she got up and left. Never returned any of my messages after that. 2.7k ...
    via r/AskReddit
  • 11
    Font - ciaonastja · 3y I asked his name in the middle of the date 1 1.5k ...
    via r/AskReddit
  • 12
    Organism - SentientDust • 3y Not exactly a date, but there was a girl in my class I tried hitting on, and it turned out she was married. Then it turned out she didn't even realize I was hitting on her... Then she actually gave me advice on how to ask a girl out without sounding like an idiot. =( 441 ...
    via r/AskReddit
  • 13
    Mammal - emedemueca · 3y I didn't know it was a date and brought my (very new) girlfriend to the movies with us. 2.9k ...
    via r/AskReddit
  • 14
    Human body - [deleted] • 3y Apparently, the date was a formal event. She showed up in a white dress. I showed up in a Star Wars t-shirt. It sucked to be sixteen. 863 ...
    via r/AskReddit
  • 15
    Rectangle - Neon_Carnivore • 3y 1 Award I sneezed just as we were about to kiss.
    via r/AskReddit
  • 16
    Font - RawrlhavePi • 3y I had a first date at a sushi restaurant/bar with a guy from OKCupid. He was hilarious and was making me laugh a lot, so it was going really well. I jokingly tried to tap his nose with my chopsticks, but mis-aimed and jammed them up his nose...full of hot sauce. D; At least he could breathe well for the rest of the night. D; 553 ...
    via r/AskReddit
  • 17
    Font - impossibru65 · 3y I have volatile allergies. My nose may have started bleeding during a New Year's kiss with a beautiful girlI met that night. It may have gotten in her mouth by the time we noticed. And I guess she maybe ran to the bathroom and threw up. Please don't look at me. 4 732 ... +3
    via r/AskReddit
  • 18
    Font - WalkingPetriDish • 3y I hit on the waitress. I didn't know it was a date. I just thought we were friends going out for dinner. My friend set us up, and they both thought it was a date. Neither of them has talked to me since then--which was around 2003. ...I'm not good with social cues. 1.6k
    via r/AskReddit

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FAIL embarrassing cringe askreddit relationships ridiculous Reddit dating
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