“56 Insane Dating Stories So Bizarre You Won’t Believe They’re Real”

2001, my friend is seeing a dude and they LOVE the idea of their friends seeing each other, us doing double dates. I meet the friend and immediately think I’d rather stay home and hem curtains. But hes nice, respectful. I dont know WHY I let it go on for multiple dates and then 🛏 . This man was a talker, and I dont mean 🔥, he was like “so when do you finish up your degree again?” And “are you thinking of trading in your car?” Like casual small talk. That was the last date because, what??

zeebo1999 Report

Met a guy at a bar in college and we really hit it off . We danced and talked all night , etc. We go back to my place and smoke with my roommates and everyone likes him . Finally , we go to bed and do the deed. I wake up the next morning and he’s gone , but not only that ; all my roommates prescription medications were stolen . I was heartbroken and LIVID, not to mention embarrassed. Worst part ? 5 weeks later I find out I’m pregnant .

susannahinthesun Report

At his house, dude came strutting out wearing nothing but a ridiculous zebra print thong/pouch thing. I instantly laughed, thinking he was doing this for comic effect.
He was not. And proceeded to get whiny and refused to accept an apology. Had it been a solid color I would not have laughed ; it was the silly zebra stripes that set me off.

badkitty1995 Report

I had the cashier at Trader Joe’s flirting with me. Dug him out of the ether via fb. My mistake. Date was a disaster; he wanted to meet at an arcade, failed to specify which city. Found him, finally. I had a gall bladder attack by the end of the date.
He told me all his baby custody woes, then came out to me as a furry goat. I caught a flight the next day to a vacation (that i told him about); he spent the next 48 hours crashing out via text.

thatblondegirlvikki/ Report

On a first date with a guy I met on Hinge. Bad conversationalist. Asking him a bunch of questions, getting nowhere. Asked his favorite holiday, a standard question. He said thanksgiving. I then asked his least favorite holiday. He said JUNETEENTH. This was almost 3 years ago and it still blows my mind. No, he wasn’t black.

jay_moose_17 Report

Good grief.
I went for dinner with one guy 10 years younger than me (he was about 45) with a full set of NHS dentures….

bonkersblonde Report

Tinder date – I had two cats at the time, this guy knew this, it had come up in conversation. First date, everything is going well, there’s banter, it’s comfortable. Then I start talking about my cats and he shuts down. I ask if something is wrong and he goes oh I just hate cats, if I ever see one I kick it. I walked out and blocked him

auraandalchemy.perfumery Report

Dated a guy in a local Ska band, 10 years older than me, divorcee, and bro WENT BALD and broke up with me 2 weeks after telling me he loved me more than he ever loved his ex wife

viscerinn Report

Went on a date. He never blinked or smiled. He just stared at me the entire date. He had that deranged look. He kept mentioning how pretty I was, but it was strange. I kept feeling like he would jump across the table and randomly attack me.

love.jadatroi Report

Had a guy ask me out for a first date and asked if I’d mind double-dating with a friend of his. I said, “sure. Why not?” It was just pizza.
The double date was with his Ex of less than 1 month and some other guy. None of them had an ounce of personality and my date and his ex were uncomfortably weird throughout. I ended up carrying the conversation and entertaining them until I could escape.

philipbendertymon/ Report

I was 17 and it was one of my first dates ever. A childhood friend asked me out to the movies. The guy wouldn’t let me go to the bathroom alone, kept saying women need a firm male hand to live a pure life, and got all gropey. I literally snuck out during a loud scene, ran to the restaurant next door and called my stepfather to come pick me up. That guy called my house for weeks pissed I would insult him like that.

birdinarizona Report

First date. FaceTimed his mom so she could “inspect me” to make sure I wasn’t “fat”. He mentioned that she wanted to know if I had any “fat friends” because they’d influence me to gain weight. He also told me I wasn’t allowed to eat cheese or bread in front of her. Truly a sick woman. So much more happened that date too. There wasn’t another date needless to say.

savannah_alexis6 Report

He didn’t want me to know what car he drove because he was afraid I might be a gold digger. It was an Infinity. Like good for you I guess, but where’s the gold I’m supposed to be digging?

juliebrown_89/ Report

I invited a potential date over to hang out at my place. He came in his WRX, and brought his own brew of beer.
I don’t drink, but my house mate and his partner did. So they shared.
We all then sat down to play Monopoly. It was supposed to be a fun afternoon of getting to know each other.
He lost at Monopoly, and cried, throwing some of his game pieces around in a tantrum.
He was firmly asked to leave.
I was 25 he was 28.

madasdesigninghatter Report

A friend sets us up. We go with friend on double date. My date “forgets” his wallet so I pay for dinner, drinks and pool. I leave and find out the next day that my date goes home with the friend that fixed us up.

shineonjds Report

Not mine but my wife’s before we met. The guy is all kinds of odd and she thought she’d have him over for dinner at her mother’s house (I mean, I love that…) anyway, the dude starts telling her and her mother how “sensual” a turkey is… we’ve been together for 25 years and still laugh about the “sensual turkey guy”

read.this.first Report

Single mom on a dinner date. The appetizer came and while we were snacking, he casually told me that he liked me but it was too bad I had a kid.
I didn’t stay for dinner. I had the doorman get me a taxi, and I went home to someone with no conditions on their love for me.

lowermom25 Report

Went on a first date with someone who proceeded to tell me he was still in love with his on-again-off-again ex after we just so happened to drive past her apartment. He later proceeded to share throughout the date that he’d been quite promiscuous, which has led to STDs and then further shared that sleeping around is a way he copes with depression for which he’s been hospitalized on more than one occasion. I don’t know what truth serum he took, but my god, did he lay it all out on the table.

birdiepnw Report

Just the usual. We meet on a dating website. She says she’s just starting a relationship but would like to hang out as friends. She meets my son, I meet her boyfriend, aaaaand the whole time, I was being groomed as a third. Everyone’s been through this to some extent. Most just haven’t realized it.

nightzac666 Report

Met someone on POF I believe. Talked/texted for a week or so then actually had a date. Had a bite to eat and talked and walked in a large city park. Conversation was good, ended with a really nice kiss. She said she would text me when she got home and we could plan our next date. A few hours after I got home, she texted me saying ”this ain’t happening but thanks for the food”..

paulied1977 Report

This guy thought he was going on a first date, but it was really just a friends dinner. He didn’t drive, so he needed a ride to the “date,” and when he realized early on that it wasn’t what he expected, he sulked the whole time, pushed his food around on his plate, and then still needed a ride back to his dorm (!) and was sullen and quiet the whole time, on the verge of tears. A little while later, he called and played Smiths songs over the phone while crying. Plot twist: This boy was me

drzachary Report

Went to a restaurant and the guy tried to vape on the patio where we were seated. The waitress caught him and told him he couldn’t do that. He tried to lie and say he wasn’t going to, he was “just holding it” (juvenile) then as we left he flipped her off and she screamed us out of the restaurant, but I hadn’t seen him do it so I was VERY confused about why she was screaming at us 😅 I told him goodnight and came back and apologized to her.

awildkendraappeared Report

1st time this particular date came to my house. My cat was being … well a cat. I moved her off a throw she was making biscuits on so she didn’t damage it. She did a cat and as soon as I sat down, went back to start doing it again. Date lept up yelling with fist clenched that he would sort that bastard cat once and for all. He was really raging. Nope nope and nope

paulinemarley7 Report

Told me he loved me on the first date, and thought he meant it.

bryteeyes_ Report

Went on a second date with a guy I wasn’t sure about. We brought our dogs on a walk on a public trail. After regaling me with tales of his refusal to take antibiotics in different situations and having strep throat for an entire month as a result (prompting me to wonder what else he might have untreated), he asked if I wanted to check under his clothes for ticks. Hard pass.

audreygcannon Report

I was 16. I worked with this guy and he told me he was still in HS. Used to show up at the library and ask me to help him study. Asked me out and he drove us around to visit crime scenes off of a scanner he had in his car. It was weird, and I was no longer interested but he kept making it awkward at work. So I went to my manager to ask for different shifts and that’s when I found out he wasn’t 17, but 20. He was using his younger sister’s books to pretend he was still in HS.

sarah.garcianelson Report

When i was a teenager, long before cell phones, I date a really nice guy from HS. 1st date, we got mugged, 2nd date, car breaks down & cant get a tow truck for 8 hours. 3rd date was fine, dinner & a movie, 4th date we’re with another couple who are his friends & the other guy is driving & he gets pulled over for making a right on red. Driver gets arrested for an outstanding warrant, the car is impounded & we have to figure out how to get ourselves home. There was not a 5th date.

laurelneiko Report