1. By Stealing From her
I offered to pay for the bill.. she insisted on paying half. Didn’t 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…
2. By Joking About His Medical Condition
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.
3. By Electrocuting Himself
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 wasn’t 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.”
4. By Slamming Her Head On The Floor
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.
5. by Forgetting Her Wig
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.
6. By Not Getting the hint
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.
7. By Crying At ‘King Kong’
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.
8. By Bringing His Girlfriend
I didn’t know it was a date and brought my (very new) girlfriend to the movies with us.
9. By Bringing A Cock Blocking Dad Along
Basically, I messed it up by having my dad drive us home.
we had gotten to her doorstep and I had walked her there and I go in for that goodnight kiss and I land it and my dad shouts “LETS FUCKING GO DUDE, IT’S 10 PM.”
I got in the car and didn’t talk to my dad for a while after that. I was pretty mad.
10. By Sneezing Directly into her open mouth
I sneezed just as we were about to kiss. Open mouth and everything.
11. By Bleeding On Her
I have volatile allergies.
My nose may have started bleeding during a New Year’s kiss with a beautiful girl I 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.
12. By Eating Her Favorite Animal
Brought a girl out for sushi and unknowingly ordered baby octopus. Turns out octopus are her favorite living thing.
13. By Drinking Gasoline
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.
14. By Being The Opposite of smooth
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.
15. By Flirting With The Wrong Girl
My aunty – yes, my aunty – set up a date for me. I am half Asian and half European. So when I visited my family in Asia they wanted me to date and probably marry this chick because she comes from a rich family. So we met at a restaurant and she brought her brother. He brought his girlfriend. I went there with a cousin, he thought it was hilarious. We introduce each other but it’s loud and they mumble so I don’t understand their names. I decide not to ask them all for their names. Didn’t want to be rude.
So I talk to this chick and she is educated and good looking as well. I start to think: Hey that wasn’t a bad idea. I actually like her and we seem to be on the same wavelength. I start to flirt with her and she seems to like it. Then suddenly the brother says something and they just leave without saying anything. I am totally confused.
Turns out I was flirting with the brother’s girlfriend the whole time and I never even looked at the girl I was supposed to date except when we introduced each other.
16. By Having A Nightmare About zombies
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 are 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.
17. By Getting hit by a car
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 never dated her again and now I’m pretty sure she’s a lesbian…
18. By Ordering Two Margaritas
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.
19. By Suggesting Chinese Food
We were trying to decide where we wanted to eat and I suggested Panda Express. She hesitated before saying no. Then I suggested Asian Buffet, once again no. I got bold and said Benihana. She told me to take her home. She told me later she thought I was being racist because she was half Chinese. I didn’t even notice. I only saw her black dad and assumed her mom was Hispanic or something. I ended up getting KFC.
20. By forgetting his name
I asked his name in the middle of the date.
21. By Poisoning Her And offering to bury her ferret “viking style”
Took her out to Italian because she said she had never had Italian food (from Venezuela). Asked me to order for her, I order carbonara, she starts eating it, asks me if it has milk in it and then runs to the bathroom because it turns out she’s lactose intolerant. So I poisoned her.
THEN I take her home and the minute she gets there she finds out that her pet ferret isn’t conscious anymore and she decides she needs to go to the vet and that I need to come with her. Okay, fine, we get on the subway with a semi-awake ferret which, it turns out, is the one animal people universally hate. So strangers are telling us how vile ferrets are, she’s crying, I’m just sitting there trying to figure out when this first date will end.
We get to the vet, they take a quick look at the ferret and take us into this room with soft lighting, nice furniture, art on the walls and tissue boxes. We’re in the bad news room. They say the ferret needs to die and it’s going to cost $500.
I think that’s stupid and I turn to her and say “we could do it for less” and then I say two words “Viking funeral”. That was my actual reaction. I detail to her my plan to put her beloved ferret in a box, douse it in gasoline, put it out on a river and light it on fire.
She paid the $500.
22. By Letting Her Brother Sit On His Lap
In high school, went to my girlfriend’s house after a date. I motioned for her to sit on my lap and she refused. But her brother took up the offer, and I was a good sport about it. She ran to her room crying.
Apparently, her brother was gay, had said something to her about thinking I was cute and had previously sucked off one of her exes. She thought I was falling for her brother…
Things didn’t last long after that.