10 Insane Dating Horror Stories That Will Make You Die a Little Inside

Reddit is the undoubted, uncontested Internet king of sites you can tell your most horrifying stories on. Here, some brave Redditors recall their darkest, most twisted dating stories.

Feel the sympathy pains…

Note: Original posts are adapted for clarity and brevity.

“Certifiably Crazy”

Submitted by Ahead 002; date from OkCupid
Went on a date with a girl who told me about how she eats 8 klonopins a day. Immediate red flag, but I had been single for almost a year and agreed to a second date. It just didn’t click. I couldn’t get over how certifiably crazy this girl seemed. Told her I didn’t want to go out again. She gets my OKC account banned, cusses me out on Snapchat, then sends me pictures of her firearms telling me to watch my back. I’m just glad we never exchanged actual phone numbers and she has no clue where I live.

“Romantic Feelings…Crushed”

Submitted by Samanthais
So I went out with another girl. She seemed pretty cool, but a little on the weird side. But she had good taste in music and was into all the same nerdy shit I was into, so I went with it.

We went on a few dates, made out once. I took her out to dinner and then we went to a gay bar for some karaoke. She left me to go chat with the boys at the bar while I sat alone at a table.

They kept buying her drinks and she got more and more drunk while I sat there sipping my beer waiting for her to come back. Eventually a group of college-aged lesbians walk in and she immediately wanders over to them. They all go back outside for a cigarette. I sigh, and finish off my beer. My date and one of the other lesbians come back in and walk towards the back of the bar towards the bathrooms. They stop, and start making out against the wall.

I left, but my date followed me out. She cried and begged for me to not leave her there and that she was drunk and made out with strangers sometimes. All romantic feelings were crushed right then and there, but she and I still hung out as friends for about a month. Then one day she made the moves on me. I declined. She punched out a window and then ran out into the middle of the street and laid down. I drove away and cut off all contact.


Submitted by McJagga; date from OkCupid
I met a girl and we decided to do a double date as she was nervous. The night was fun and her friend was pretty cool. The next time we met up we planned to do MDMA together, just her and I. I had been doing it a lot that summer and she was just a random user.

So about 10 minutes into it she goes insane. She took off all her clothes and started flailing on the ground hurting herself. She was soooo horny trying to get me to have sex with her but I was scared shitless because she was acting insane and I thought she wouldn’t remember what happened accused me of drugging her to rape her. I called her friend over to help me restrain her and so the friend could see I did not in fact try to rape her.

The friend brought a guy as well and they all witnessed how crazy she was being. We all hung out in the living room while her friends held her hands and feet together because she kept trying to masturbate and it was awkward as fuck.

After a few hours she sobered up and cried in my arms feeling so embarrassed for what happened. I was very nice about it to her even though I thought for sure I was going to jail if the friend wasn’t able to be there.

A few days later she messaged me to do MDMA again. Nope.

“Slap For Whiskey”

Submitted by Astrocats
Met one guy who had just moved to my area and was looking for a NSA situation. At the time, I was okay with this, so I decided to meet up with him.

He worked at a gross tattoo shop and had super greasy hair. I realized he was good at working the angles in his pics. We proceeded to get shithoused at a bar together (since I figured we could at least be friends), and things ended up getting… weird.

He was a submissive, so he basically asked me to slap the hell out of him in public in exchange for more whiskey (obviously I obliged). We ended up going home together where I discovered he had 5 cats that all had human names. He baby-talked to all of them and they were super possessive of him, to the point of slamming themselves against his bedroom door trying to get in when we were in bed together. I soldiered through some awkward sex, he gave me a necklace, and I ran the hell out of there. Never talked to him again.

“I’m What Hipsters Aspire To Be”

Submitted by ceeeloz; date from Tinder
Went on Tinder date with a guy who was actually really cute. We go to dinner where he proceeds to tell me his entire life story, how every person he meets lets him down and his friends are horrible people. He also mentions he recently lost 150+ pounds by replacing food with ecstasy. So already a winner.

We go back to my apartment to just hang out I guess, he takes out a bong out of his backpack and back to back smoked 6 bowls of weed. I decided things were already bad so I might as well get really stoned so I joined him. He then showed me all his favorite subreddits, none of them appropriate to a show a first date whatsoever. He then shows me a 30-minute video of him at a rave, in which he is making out with a girl for part of it.

Best quote from him was, “I’m what hipsters aspire to be.”

Overall he was kinda sweaty and would randomly dance, he played a shitty playlist and tried to pull some moves, I was like “See ya dude.”


Submitted by ULiKaDaJuice
After thinking this girl I met was normal for an extended period of time I decided to take her out on a date. The whole evening she was making cat noises. I shit you not — cat noises. Now I tried to give her the benefit of the doubt and maybe she was nervous. But the very next morning she sends me a text with a cat emote and the word meow. I even ignored that (because she had huge boobs) and we dated one more time not only did the cat noises continue but she climbed on top of me removed her shirt and starting rubbing her armpit hair on me whilst doing the cat noises.

“Dodged a Bullet”

Submitted by WESTOFTHEOCEAN; date from OkCupid
Several years ago, a friend of mine went on a date with a guy who had a weird/creepy vibe. She couldn’t quite place what was wrong with him. After the second date, he offered to drive her home. She was uncomfortable with that and said no, as she didn’t want him to know where she lived yet, but he kept pushing. She eventually was able to call a cab home.

Several months later, after they had lost touch, he was in the news for trying to blow up/set fire to the Golden Gate Bridge. Can’t seem to find the articles but I’m glad she dodged a bullet there.


Submitted by Electron-shock
We meet at a local pub for a few drinks, and we get chicken fingers. The conversation is terrible, but I notice she’s taking the chicken fingers and ripping them up in her hands and putting the breading in her huge purse. So naturally I call her out on it. She smiled and said “Oh, I’m just feeding Sammy” and pulled out a fat chinchilla from her purse. She plopped the thing in the middle of the table and it just kinda chilled out. I played with the chinchilla a bit and she kinda got mad at me for playing with it and back in the purse it went. I was ready to call it and leave, but she mentioned she could go for some ice cream, and I was cool with it.

So we go to Ben & Jerry’s. We get to talking about tattoos and piercing, and she tells me she has nipple piercings, and I’m like “Oh?” and then she pulls down her shirt, in the middle of Ben and Jerry’s at 8pm and shows me her nipples. I just kind of poker-faced. So then I decide to walk her to her car. She kiss attacks me, and well, she WAS kinda cute so I made out with her, sort of…her lips were tense the whole time and she licked my teeth. I friended her on Facebook for some reason after that, she had a Facebook page for her chinchilla that had more Facebook friends than I did.

A few months later the chinchilla died and its Facebook was a memorial page where a bunch of people commented how much they missed it. I ‘liked’ one of her statuses and she called me crying.

I unfriended her but not the chinchilla. RIP Sammy.


Submitted by rainmanak44
Met up with a girl for the first time after talking for a few weeks. She is attractive, fun. Lots of things in common. During the date she keeps checking her phone and acts annoyed by someone. Finally she apologizes for it and tells me about some creepo stalker dude that won’t leave her alone. And I guess to prove it she calls him and kinda loudly says “stop contacting me or I will call the police!”

Forward to end of date, she says she had a good time and wants to do it again sometime, kinda flirty. Then outside before she gets in her car she goes in for a long passionate kiss. Then says, “call me” and winks!

So I call a couple days later. No answer. Text the next day, no answer. Call in two days and finally she answered the phone and says kinda loudly, “Stop contacting me or I am calling the police!” I could just see her on a date playing the stalker victim again!

“Yours Are Yellow”

Submitted by unknown; date from OkCupid
I was 24 and, from school, had been messaging this cute girl who could actually hold a conversation really well so after I got home in December we decide to meet up:

7:00 p.m. – Show up at her place, she isn’t 120 lbs heavier than her picture, doesn’t have a beard or Adam’s apple, and hasn’t ax murdered me yet. Chemistry is great and we actually start making out before I pull out of my parking space. So far so good, OKCupid, you da bomb.

7:15 – In the car, things are fine, she’s talking a lot about her modeling job, which is cool.

7:30 – Arrive at ice rink and race each other inside, this is fun.

7:35 – Inside and she’s still going about her local modeling career and all the free things the vendors and designers give her. Thrifty, cool.

8:45 – Been skating for a while, I now know about the process of applying “runway makeup”, the time constraints and approximations of changing outfits depending on the number of pieces, and how to adjust hip tilt and swing during a catwalk if your clothing piece is top heavy vs. has a long train. I now know every cost approximation of at least 12 different clothing pieces from 3 designers I have never heard of.

8:50 – She can’t talk if she’s eating, so I suggest we get food.

9:00 – We arrive at the place. It has 40ft high wooden vaulted ceilings with hanging sheer fabric for ambiance and the swankiest fucking bar I’ve never seen.

9:03 – Sitting down. She’s been bragging for a bit, that despite being a model, she has never done cocaine. Fuck, the prices are steep, I’ll just have a soda and a salad. She knows everything on the menu by name and what it should be paired with.

9:30 – I would really like some cocaine.

10:20 – Michael Kors ain’t got shit on me for knowledge of the fashion industry.

10:30 – I have no idea what she ordered but the bill is $105 plus tip. She asks if we should go and I say “yes”, she makes no attempt to pull out her wallet so I bite the tab, trying to conceal my pissed-ness.

10:40 – Not too impressed with the date but I walk her to the door. She asks if I want to come in.

10:41 – I meet her mother, in a bathrobe, completely unfazed by my presence. She asks if I know how to fix a light socket.

10:47 – Light socket is fixed.

10:50 – In her room, score!

11:10 – She has taken me through every lotion and perfume and tin of makeup and brush on her vanity and told me the brand, the list price, and how much she actually got it for.

11:20 – She is almost finished telling me the brand, location of purchase, and price of every shirt, skirt, pair of pants, and jacket in her closet. She is upset that her friend “stole” a bracelet from her 2 weeks ago, she wonders if I would help her look for it.

11:35 – She is literally crying, with tears down her cheeks, because I could not find the “stolen” bracelet behind, under, in her dresser/vanity/bathroom/bed/closet/night stands/carpet.
(If it was stolen why did she ask me to look for it in her room?)

11:40 – She has stopped crying and suggests we watch a movie.

11:45 – PayPerView, or something, Evil Cabin Zombies in the Woods Dead 27

12:00am – Extensive commentary on the superior quality of acting begins and ensues for the duration of the movie but she says she has a knot in her back and wants me to massage it out.

12:30 – Her shirt is off and she is dead-set on me massaging out a very specific knot on her left shoulder which does not exist. Whatever.

1:00 – Movie ends, my arms are getting sore, been kissing her sensually for a while, have not been able to get her to A) shut up, B) turn over, C) actively engage said kissies.

1:03 – Sequel to movie begins.

2:00 – She starts participating in the making out stuff and politely tells me that for religious reasons she is saving her virginity until marriage. I completely understand, when it comes to faith beliefs like that, I respect whatever choices you make, cool, no hassle, and we start fooling around.

2:30 – I am excited, I’ve finished her off about 2 or 3 times, I feel like a champ, but I am still completely clothed and have not been touched in any way, shape, or form. As I am still being all sexy-like, I casually say, “What about me?”

2:31 – She informs me that the bathroom is right over there and tells me I can take care of myself in the shower. I think I’ll just hold it.

2:45 – We’ve been silent, cuddling. Hey, this is nice, I love cuddling, she is comfy, and she’s not talking, this is good.

2:50 – Out of silence, she whispers, “I see demons. Yours are yellow.”

2:52 – I shit myself

3:00 – I learn that my demons are angry and she is scared of them. She tells me that she has been exorcised on two occasions and it’s helped a lot. I don’t inquire as to how much, precisely.

3:05 – I try to be supportive because this doesn’t seem like the kind of thing you just go around telling everybody, and more or less keep my mouth shut. God I want to try cocaine.

3:10 – Sleep for her, another hour of being stiff as a board and scared before I pass out.

9:00 – Her mother knocks and I, all 6’5 220lbs of me, attempts to hide under the blankets. Mother comes in and nonchalantly tells her that they are going to a friend’s house for dinner, asks if her if the bearded guy under the blanket wants to come, I decline, I have to go return some overdue video tapes.

9:15 – I leave to return some overdue video tapes.

Bad date image by Shutterstock