37 People Share The Worst Date They’ve Ever Been On

Here are all the worst date ever stories… prepare to cringe…

Found on AskReddit.

1. When the guy shares too much about his ex-wife.

I went on a date with this person who spent the entire date telling me, while we were in a crowded Mexican restaurant, first, how much he hated his wife but wouldn’t divorce her because he hated her so much that he didn’t want her to have anything he had, followed by the detailed story of her suicide.

2. Turns out the date was a delinquent.

I had a great date I met on Match.com and I was walking her home at the end of the night and suddenly she started to run away. I started to chase after her and asked her what happened and she just said “Police! I have a warrant out for me.” Well when I found out she had a warrant I kept running, but a different direction than she went. I eventually got caught by the cops and I had to spend a good 20 minutes explaining to them the situation and how I was in no way involved in her crack cocaine dealing ring.

3. A racist date.

I had my first date in like 3 months after ending a serious relationship. She told me she’s scared of sleeping with a black person because of AIDS. Welp.

4. Caught with the worst dudes of all time.

Went to the zoo with a guy, we rushed through it and he wouldn’t let me see much of anything because he had a hair appointment he just had to keep. He was getting his remaining hair frosted.

Second and last date, he left me sitting alone at a table in the park for around a half an hour because he saw a tree he simply “had” to meditate under. Alone.

5. Date who turns out to be a relative.

Out on a first date. We’re talking about mutual friends, neighbors, family, etc., and LOTS of the names are familiar.

Long story short, I discovered that she was my second cousin. Yay, rural Kentucky.

6. A date with gross fetishes.

My first attempt at online dating lead me to what was a strange courtship. When we finally met up one night, she told me she had fantasies about me raping her and doo dooing on her chest.

I hope she has found a life mate. That guy needs to be off the streets.

7. Date claims she’s a witch.

On date, sitting at bar, when my date informs me that she was a witch, and that she had made her last boyfriend love her by casting a spell on him. She was even nice enough to tell me how the spell works. She took a vial of her period blood and poured it into his wine, and tricked him into drinking it.

“Now he’s mine forever” she told me.

She went on to say that it turned out she didn’t really love him, but because of her spell, he would love her forever. She claimed he was still desperately in love with her even though she had dumped him.

8. Date who ends up being PRETTY into drugs.

This weekend actually, got invited to a party as a second date. Girl met me at the door and walked me to where the band was playing, she then walked away with some guy. I didn’t see her for a good hour before I decided to leave. Turns out he had some coke and she fucked him to score some. Guess he did me a favor.

9. The ultimate double whammy.

I once went on a date with a Jehovah’s Witness drug dealer. In my defense I didn’t know she was a Jehovah’s Witness at the time.
And to be fair, I didn’t know she was a drug dealer either.

10. Proselytizing date.

  • 5:30 – We meet at 50s diner next to my work.
  • 5:35 – She orders a milkshake.
  • 5:37 – She asks me about Jesus in my life.
  • 5:39 – “Maybe you need to read the fucking Bible!”
  • 5:42 – “If Gandhi did not accept the Lord Jesus Christ as our one and ONLY savior, then he is BURNING IN HELL! AND SO WILL YOU! But the Lord can still save you”.
  • 5:44 – I put $10 on the table and simply walked out of the door. “What! Are you just going to leave me here?”

11. A date with disturbing intentions.

My date told me her plan to poison her boss. I heard her out part-expecting a “just kidding” at the end of her twisted story… There was no “just kidding.”

12. Possibly the worst OkCupid date ever.

Met up with a girl from Okcupid, then in approximately this order, discovered she was:

  1. Larger than she appeared in her pictures
  2. Polyamorous (this one ain’t so bad I suppose but in the context of the others…)
  3. A foot fetish dominatrix on craigslist who also responds to missed connections posts just to troll people
  4. Homeless

I ended up buying her some cheap Chinese grub and dropping her off at her friend’s house to stay at, and on the way there we almost managed to bond over video games and mind-altering substances. Almost.

13. Too emotional of a date.

Girl broke down and started crying in the restaurant because the abortion she secretly got when she was younger was something she always regretted. All I asked her was how her day was going.

14. Dumbest date known to man.

My worst date was with a girl who thought that Islam was a country that she wanted to go to. Her head was so full of air that when we left the restaurant and she invited me back to hers I started to make excuses why I couldn’t stay. She was so persistent that in the end I lied that I was a Christian and basically said that I thought that it’d be inappropriate to go back to hers.

15. A date that turned into an accident.

I was on a second date with a guy I met on the Internet. Boring guy, fast car. He decides to evade the police while driving 120mph on the highway, takes an exit & I end up in an upside-down 350Z, which had rolled over at 90mph into a stone wall & a telephone poll. Over a year of physical therapy. Minor nerve damage. Will never Internet date again!

16. A date missing some essential limbs.

I once talked to a girl online for some time; she was really smart, quirky, funny and pretty cute. I enjoyed the conversation and thought I was in for a treat. When I saw her for the first time I learned, she had no arms, and that was a bit of a surprise- I didn’t know how to react.

17. Scariest date of all time.

I went on a date once with a guy who intended to study mortuary science. He asked me how I’d feel about taking a cold bath before sex, and then staying very still throughout. I couldn’t get out of that car fast enough!

18. A girl with a gun.

Somehow got on the topic of CCW permits on a date with a girl, she asked if I had mine.

“Yes.” “Do you have your gun on you?” “No, we’re drinking at a bar and there’s a posted sign on the door, so..that would be a terrible idea.” “Oh, I have mine! Want to see!?” Before I could say no, I had a Sig Sauer p238 pointed at me. Never in my life have I moved faster out of the way than I did that night. I took it from her, field stripped it (chamber was empty, thank god.), put the pieces back in her bag, walked her home and said “Never contact me again.”

That sucked.

19. A date that turned out not to be a date at all.

A guy asked me to go to a concert with him, when I got to the venue, he also brought his girlfriend with him. I haven’t replied to his messages ever since.

20. The worst homecoming date of all time.

Homecoming formal my junior year. My first dance ever, my date picks me up 30 minutes late, realizes he isn’t wearing a tie or appropriate shoes, stops at the store, steals a tie and some shoes (because apparently he really felt like he was “fucking the man”) forgets that he never made dinner reservations, we end up eating a $50 meal (he got steak, I got a salad), forgets his credit card, I end up having to pay for both our meals, he tells me he just took ecstasy, ends up freaking out at the dance, leaves me by myself and I end up having to call a cab home. Did I mention he sat in front of me in 2 classes?

21. A crazy, suicidal date.

After dating a girl for about a month, she let me know that she had spent time in a mental institution two different times for trying to kill herself. She did not do it because she was depressed or something like that. She did it so she could enter “The land of the dragons”. As if that was not bad enough, she said that she still wanted to get there some day…

22. Shocking surprises.

Online dating has had some horrors….

One guy failed to mention he DIDN’T HAVE TEETH. And after he revealed this (in person) proceeded to invite me to get food. WUT?

Another came to a date SO HIGH… he couldn’t hold a conversation, except when he started talking about how he needed to harvest his plants. SMH.

23. A date who claimed to have been raped by aliens.

A girl I met at a party told me that not only had she been raped by aliens, but that her psychic told her that we were a good match. She also felt the need to apologize for treating me poorly, in a past life…

24. A very dumb-witted date.

Went to a date with this gorgeous girl I’ve had a crush on for a while. She is thoroughly convinced that the sun revolves around the earth in a perfect circle. I paid the bill and left.

25. Turns out the date’s dad is in the mafia.

Went on a date with a girl and when I picked her up discovered that her father was apparently a big mafia guy. Still diddled her because she wanted to, but just that once, and it wasn’t fun.

26. A date in which he had to pretend he was gay to please her parents.

I went on a date with a cute Lebanese girl, she was really smart and cute, we would Skype etc. and it all went fine. But I met her and she told me I had to meet her mom and say I was gay and that she was helping me find Jesus since her parents won’t let her date. Well I met her parents with them thinking I’m gay (nothing wrong with gays by the way), and then she decided she can’t kiss or even hug until engaged.

27. An awkward date.

I went to dinner recently and she came back to smoke afterwards. I had full intention of kissing her, but when we got into my room I didn’t close the door behind us and felt weird about getting up once we were sitting because I didn’t want it to come off as “LET’S FUCK NOW”. Also my roommate was in the living room and could here us joking around and would let out the odd chuckle making me super self-conscious. At one point I decided to make the jump but was so in my head that I only half jumped. What I mean is, when we hit a lull, I put my arm around her and instead of kissing her, just leaned us both back so we were lying down and THAT’S IT. I just laid there awkwardly for a few minutes until she said she had to go. Never saw her again haha.

28. The least gentlemanly date.

I once went on a date with a guy, and while we were driving to dinner we got a speeding ticket. He asked me to pay for the ticket, because I was distracting him, and then took me to dinner where he made me foot the bill. After that he took me to a nightclub, where he told me about other girls he brought there. I then made him take me home, and told him to forget my number.

29. Self-harming date.

With a woman who taught little girls ballet, first date: “I think five needles pushed through the skin on the wrist is better than an orgasm.”

30. A date who was much better looking the first go-around.

I agreed to go on a date with a woman I had drunkenly hooked up with, I walk into the restaurant and I’m turning my head looking for her and from my right I hear “Oh hey Pepino!!”

ಠ_ಠ She was NOT that ugly when I was drunk. I still went through on the date and was all gentlemanly, but…damn. Never called that one back.

31. A girl brings her friends on a date.

I went on a movie date with this girl, and she asked if she could bring friends. I figured she meant a double date, so I said yes.

She brought NINE OF HER FRIENDS to the date. NINE. We didn’t even sit in the same row, and I never got so much as a phone call. When I ran into her later, she said that the reason she didn’t call me was because I didn’t talk enough.

32. Most annoying date ever.

Had to sit through Christmas With The Kranks while she argued about politics in my ear and tried to convince me she could talk to ghosts.

33. A delusional date.

I once met this girl who seemed nice at first, completely innocent, nothing seemed to be wrong with her at all. We went on a couple dates and all seemed normal and I started to like her. Until weird things started to occur, it began with her telling me that she gets raped 38 times (in a bragging manner), then told me that she turns into a werewolf every night and she wanted to me fuck her multiple times while she was on her period. Then she proceeded to try and get with my best friend and told him she was going to suck my blood to win his heart; needless to say we both dropped that bitch.

34. A date with a pedophile for an ex-husband.

I went on a date with a match.com chick. Ends up not looking like her pictures (of course) and she doesn’t drink alcohol (snoooooooze).
Halfway into dinner, she starts talking about her ex-husband. I’m actually okay with talking about past relationships so this was fine. But she then explains how he was a pedophile…and how she stayed with him for years because she wanted to make the relationship work.

35. A date with little drive.

I once dated a girl who never worked in her life and chose not to go to college because she didn’t like homework, getting up early, or having to take notes or pay attention. She fancied herself a writer, but never had anything published. In fact, she never even finished a story!

36. The ol’ phlebotomist date.

Went on a date with a phlebotomist and she kept asking to take my blood. I was terrified what she may do with it and I had to say no constantly throughout the night in fear each time.

37. A date with a man child.

My sister’s story: Met a guy online, seemed normal (don’t they all?). He requested she pick him up, which she thought was kind of odd, but she obliged. Goes to his house, apparently he’s been day drinking (it’s a Tuesday) and she has to drive. But they need to wait so he can grab some cash from his mom first. Thought Catalog Logo Mark

About the author

Charlie Shaw