Dates can go south in a hurry when expectations are high. Sometimes dates are destined to fail, other times things go wrong in an instant and derail everything. I’ve been on some pretty shitty dates in my life, but that’s not what we’re here to talk about today. Below, a bunch of people shared stories of the funniest ways they’ve fucked up dates over the years and some of these are truly amazing (via AskReddit):
I sneezed just as we were about to kiss.
Brought a girl out for sushi and unknowingly ordered baby octopus. Turns out octopus are her favorite living thing.
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.
My first night in Buenos Aires. I’m in a nightclub buying a drink. I hand the bartender local note equivalent in value to about $20. He’s saying something in Spanish I don’t understand. But I’m thinking one drink can’t cost more than $20 so what’s his problem?
This incredibly smartly dressed, beautiful woman intervenes. She explains the barman is asking if I have a smaller note because he doesn’t have change. No problem. We get to talking. I tell her it’s my first night in the city. She says “Oh, you must let me show you around town tomorrow.” She puts her business card on the bar and pushes it towards me. It has her name, her number and the fact that she’s an English Language Teacher. So in what I think is an incredibly witty, flirtatious comeback I pushed the card back towards her and say “Oh, I don’t know. My English is already pretty good.” She scoops the card back, says “fine” and walks away.
I remember thinking “Oh well, at least no one saw that.” Then I turned around and my friend is right behind me shaking his like “What a loser.” When I told that story to some Argentinians I met later in that trip, they said not to worry. The woman had probably been a con artist or prostitute targeting foreign tourists. (I’m pretty average looking and she was definitely way out of my league.)
I wore a wig for a few months after shaving my head for charity. Went to the ladies room, took it off to straighten it and then walked out without putting it back on.
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..
I didn’t fuck up the date. The date was just fucked.
Met a girl at the local McDonald’s after school one day. We talked and then exchanged numbers. She asked if I’d go out with her the next day. I thought she was gorgeous, and when she said I should dress up I expected something special.
She took me to her grandmas funeral
We were sitting on my couch watching a movie and she moves closer and closer until she is on my lap. As a joke I start to tickle her and then she starts to tickle me back and then it turns into play wrestling. Right before things switch from play wrestling to making out, we both slip off of the couch and my reflexes kick in so I accidentally move in a way that puts her below me. She slams her head into the hardwood floor. She laughs it off but it killed the mood and we went back to watching the movie.
When I was about 20 or so I got a date with a girl who I really liked, she was exactly my type and couldn’t believe my luck. We met in a local pub for a few drinks and things were great. I was getting all the good signs with lots of hand touching and the like. An hour of pure bliss went by and I needed a piss. After washing my hands I went to the hand dryer and it didn’t work and looked like part of the protective grill was hanging from it. I wanted to dry my hands because I wanted more of the hand holdy stuff. In the single most stupidly brain fart moment of my life I thought “I can fix this!” and put my hand inside the nozzle of the dryer. WHY!? WHY THE FUCK!? Obviously I got buzzed by the electric heating element, fell back and cracked my head on the wall. I didn’t get knocked out but needed a few minutes to sort my shit out before going back. I didn’t have the balls to tell her what had happened; brain fart number two.
I had a banging headache and I wasnt quite right. Not much later she made her excuses and left and turned me down when I asked her for a second date. A year or so later I found out she had told her friend that she really liked me, but I went to the toilet and when I came out I was acting really weird and she “wasn’t up for dating someone on drugs”.
I didn’t know it was a date and brought my (very new) girlfriend to the movies with us.
This girls father had just recently passed away so I invited her over to make her dinner and console her. We make dinner and we are talking about stand up comedians and she tells me she’s never seen Louis C.K. so I say we need to watch one of his standups. Well I turn on one randomly and the first 25 minutes are dead dad/parent jokes.
We met at a restaurant to get something to eat and everything was going really well. I invited her to come back to my house for a few drinks but she had had a couple drinks and asked if I could drive because I hadn’t started drinking yet and she said lets take your car.
When she went to get into my truck there was my ex’s bag of stuff I was returning to her, I tried to move it to the back seat and a bra and hair brush and some other clothes fell out right in front of her.
She took a uber home.
That was pretty recent actually lol
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 almost 7 years!
I drove a Volvo from the 60’s. The fuel line and filter would get clogged occasionally. On a first date, I pick her up. As we’re heading to dinner, the car dies. I pop the hood, knock out the crud in the filter and then have to suck on the fuel line to get it flowing again… I wasn’t fast enough and end up with gasoline in my mouth and on my shirt. She was understanding, but needless to say she wasn’t impressed with the Techron mouthwash/cologne.
Got hit by a car walking to her apartment.
I bounced off the windshield and was thrown across the intersection. Probably because I was in shock, and in retrospect the driver was drunk, we didn’t call the police. Instead, I limped to the girl’s apartment. When she answered the door, she was dressed to the nines and ready for a big night. But I had to tell her I couldn’t go out because I’d just been hit by a car and probably should go to the hospital.
She looked at me like, “Now I’ve heard every excuse in the book.”
I didn’t know it was a date and bought my little sister to hang out with her too.
Technically wasn’t a date, because we just went out as friends but it functioned as one. It was a girl I worked with. I’d been interested in her for a while but we were just friends and that was fine. Still, we hung out a lot and eventually one night we got drinks after work and things escalated. I’ll spare you those details.
Fast forward to later that night. We’re both asleep at her place. Now, I hadn’t been sleeping well all that week partially because of her dragging me out with her. And when I’m sleep deprived, I have very strange dreams and am prone to sleep walking/talking. In my dream I’m walking done this tunnel, like a metro tunnel. I see this girl on the ground crying. She’s got no clothes. I ask her what’s wrong and she lunges at me. She was a zombie or something. She wraps her corpse arms around me and I throw her off and start yelling. That’s what I was seeing. I was fighting for my life.
What had actually happened outside of the dream was she tried to cuddle with me and I responded by freaking out and literally throwing her out of the bed. She screamed and that partially woke me up but I’m still mostly in the dream. She asks me what’s wrong and I just start yelling things. Who are you? Where’s your clothes? Get away from me!
I woke up fully as she was storming out of the room. She thought I was trying to be a prick, I suppose. If I had a gun at that moment, I would’ve shot myself. No joke, I felt awful. I thought I blew it. Once I went out and explained what happened she thought it was hilarious and came back. She still gives me shit for it, though.
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 I’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.
Second date she invited me over for a home cooked meal. Fed me food and drinks, packed me leftovers and offered to let me stay the night.
Fucked it up big-time. We still talked afterwards but it was never the same and we kind of moved on.
Winner winner, chicken dinner.
Pooped my pants.
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