15 People Reveal Dating Stories That Went Hilariously Wrong

Love may feel like a fairy tale at first... until it all falls apart. We've all experienced those dates that begin with all the makings of a romantic movie: butterflies, the ideal playlist, and perhaps a cozy window seat at a chic café. But sometimes, rather than a happily ever after, you're left with a bewildering "what just happened?" moment that lingers in your memory (no matter how much you'd like to forget). Here are romantic encounters that started with promise, only to unravel into cautionary tales worthy of their own horror story.

  • I was 23, he was 34. On our first date, which only lasted a couple of hours, his mom called several times. From his responses, it was clear she was asking if he had eaten or if he was tired. It started to get a bit much. I decided it was time to leave after one call, when he told her he'd be home before 10:00 p.m. and then, looking me up and down, said into the phone, "Yeah, she's okay."
  • Went on a first date with a guy to a Japanese place. I wasn't comfortable using chopsticks and asked the boy if I should just get a fork. He tells me it's embarrassing when people ask for a fork instead of chopsticks. So I soldier on - navigating these chopsticks - and go to pick up a piece of sushi and accidentally flick a piece of wasabi. I watch in slow motion as the large piece of wasabi hits him right in the eyeball.
    He spends the rest of the date washing his eye in the toilet. I felt so bad that I paid for the entire meal after we tried to get through the last part of the date with him clutching his eyeball like an angry pirate. Needless to say, he did not contact me for a second date. © throwtheflames123 / Reddit
  • He sat on my lap and farted because he didn't want it to make any noise. Then he announced that he had forgotten his wallet when the bill came and ran out of the restaurant. © Unknown / Reddit
  • When I was at university, I was invited to a rink with a girl I liked and some of her friends. I didn't know how to skate, and I wasn't very fast, but I wanted to try and impress her somehow. Well, I hugged the wall all the time and made a fool of myself. The highlight was when I saw a flash of light as I fell in front of a group of people. It turned out that I had fallen just as someone was taking a picture, so my failure was immortalised forever. She took me back to my flat and ended the relationship before it began.
    On a lighter note, the woman who is now my wife was at the rink that night. We didn't realise we were there at the same time until a year or two into our relationship, and she exclaimed, "You were that guy who couldn't skate! Yeah, she didn't seem that into you." © Krell47 / Reddit
  • I was once a "phone a friend" for a guy I knew who was on Who Wants to Be a Millionaire. He asked me out before the question, and I said yes, because who would turn down a guy who asked you out on TV? I got the question wrong, and he lost, and I still had to go out to dinner with him afterward. Worst date ever. © TheNFernandes / Reddit
  • There was the guy who said he didn't have kids (my online dating profile made it clear that I didn't and didn't want to) and then, halfway through dinner, dropped into conversation that he did have kids, but "it's OK because I don't see them often." Dude! That's worse!
    Oh, and the guy who spent the whole time comparing me to his ex-wife. At the end of the drink, I wanted to ask for her number to congratulate her on getting rid of that fool. © liseusester / Reddit
  • Went on a blind date with a lady who wouldn't stop picking at her scabs. Just made a pile of them on the restaurant table. I excused myself to go to the toilet, and when I came back, my soup was there, but the pile of scabs wasn't. No, I didn't eat the soup. © sarin77 / Reddit
  • She was allergic to something I ate, and when I went to kiss her, her lips swelled up, and she went into anaphylactic shock. I took her to the hospital, but I couldn't stop laughing because it was so embarrassing. She looked so ridiculous, and I'd been so nervous up to that point that I started giggling. I didn't see her again. © lazytoxer / Reddit
  • I met a man — 35 years old, well-paid, smart, and charming. I thought I was really lucky. On our third date, while we were at a restaurant, he mentioned that someone would be joining us for a bit before leaving. I didn’t think much of it, assuming it was a friend or colleague. But then, his mom walked in. She told me about all his ailments, what he likes to eat, and mentioned that when it gets cold, he needs to buy lip balm. I quickly bolted out of there, my heels clicking as I made my escape.
  • I went out on a date with a girl from OkCupid. It was late (around 9 pm), and she sent me a message out of the blue. We talked for a while, and she wanted to meet for dinner. I hadn't eaten yet, so I agreed. We were to meet at a local diner.
    She went with her friend (a 16-year-old; I was 22; she was 20). To make matters worse, her friend had brought her toddler. Oh, and her friend had brought another friend. So here I am with 3 girls and a toddler I don't know.
    We sat down at the table, and it just went downhill from there. The toddler began to play with the sugar container (one of those "shaker" style ones - a big cylinder with a little flapping thing). She promptly poured sugar all over the table and started licking it up. Meanwhile, all the girls are laughing at the toddler and having a great time. They talked to each other and didn't even try to include me in the conversation. After about 5 minutes of ignoring me, they started talking about boys from high school.
    Long story short, I ate half a chicken sandwich, excused myself, apologised to the hostess/waitress for the mess and the awful people, left $50, and walked out. © go_so_loud / Reddit
  • I met a guy on Bumble whose profile said he worked in engineering Monday to Friday but was a beauty and wellness entrepreneur on the weekends. We decided to meet for a "date" at 11 am at Starbucks. I told him I wasn't a morning person and wanted to move the date to 11.30 instead, but he refused, insisting on 11 am. Fine, I turned up a bit late for our date at 11.15 am, but he turned up at noon with a mini suitcase he said was for his entrepreneurial job later- no apologies, nothing, just said there was a traffic jam. When we sat down and started chatting, he very cleverly turned the conversation to his MLM sales and tried to get me to attend his seminar that was happening right after our "date". I blocked and reported his profile after I left. © ajowanhykemain / Reddit
  • I went on an online date with this guy when I first moved back home from college. We met up, and I have a habit of telling my parents, "I'm going out, I'll be back later," without any details, etc. Anyway, this time my mom said "just be careful and if he can't drive, get out of the car".
    We went to our first destination, and it was closed. So he asked me where I wanted to go, and I said, "Hooters and bowling." His driving was so reckless... I mean, REALLY bad. Anyway, we ended up driving across town because he wanted to take me to this one place. By this time, I've decided that I'm not into him and I want out, so I just go along with it. Maybe we can be friends, right?
    His brakes gave out, and we ended up in an accident. We hit the back of a truck pretty hard, and I jerk forward, and my glasses fly off. After the smoke clears, when I'm nervous, I start laughing. He asks me if I'm okay, I say sure, and I look for my glasses, and he says, "Oh, that's bad, that's bad." So I said, "Why? No insurance?" He says, "No, I have a warrant for my arrest," and he gets out of the car and runs. As he's running off into the sunset, he's yelling back at me, "I'm sorry, I can't afford to go to jail again."
    The person we hit walks away. So I'm the only one there, and the police show up. I had to call my parents to come pick me up because I have no friends in the area, and of course, I gave the cops his info. I knew I wouldn't be able to talk to him again. The police took me to a gas station across the street while I waited for someone to pick me up. I sat back, took a picture in the police car, posted it on Facebook, and tagged him in the picture. Somewhere in the middle of running, he found time to get on Facebook and block me.
    The bad part wasn't just the accident, I didn't even get a chance to enjoy Hooters and wings. © filmpster / Reddit
  • We went to the movies in the morning and were the only ones in the theater. He stole 650 straws from the concession stand and tied them all together during the movie until they were long enough to reach the screen. We went out about two more times after that, but he started getting creepy, so I broke it off. © tsim12345 / Reddit
  • We went to meet at a restaurant that was more convenient for him than for me. When I got there, he told me to go in and sit at the table he'd reserved under his name. When I walked in, the table wasn't full, but luckily, they had a free table. I sat by myself before he came in 20 minutes late, saying he'd crashed into a car in the parking lot.
    Dinner was awkward; hardly any conversation. When the check came, he just slid it over to my side of the table, got up, and left. So I paid the bill and walked to my car, already dissatisfied. AND GUESS WHAT? The jerk had smashed MY car in the parking lot. Of course, by the time I realized, he'd blocked me on all the social networking sites, and I only remembered his first name so the police wouldn't do anything.
    So that was an expensive night for literally no reward. © ragnarsmoop / Reddit
  • Met a guy on an app. After talking to him on the phone for a few weeks, I decided to meet up at his place for our first date. Turns out the 2nd bedroom in his apartment is a shrine to his late grandparents. I figured since they raised him, it must be his way of remembering them, so I let it go. We dated a few months, and it just so happens he demands we take showers every night so as not to “contaminate” the bed sheets. We broke up shortly after he demanded my mother sign a letter saying she will respect his wishes not to meet her and have it notarized. The scariest thing about this is that he’s a police officer. Not exactly who I want out there protecting the sheets streets. © CharlieBear26 / Reddit

Ready for more unforgettable love fails? You won’t want to miss this article. After all, if misery loves company, awkward dates are sure to bring plenty of hilarious stories along for the ride.

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