40 Weird Date Stories That Will Make You Feel Better About Your Own Love Life
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40 Weird Date Stories That Will Make You Feel Better About Your Own Love Life

If you feel bad about your love life, reading these stories from Ask Reddit might help.

1. Was going to go to a bar with a girl I met on Tinder. She showed up 15 minutes late, which wasn’t that big of a deal. Got out of her car, crossed the street, and then awkwardly shook my hand. Told me she forgot her ID at home, apologized, and then left.

2. It’s hard to say I was catfished because the actual girl was there, but so was her boyfriend and her friend she thought I would be a better match with. What made it more odd, is she had sent nudes, full face nudes not photoshopped face swapped I could see the chest tat on her in person no mistaking that.

3. She brought a stuffed animal. Not a tiny little thing some (young) women clip to their keychain. It was a gigantic blue rabbit at least as big as a toddler. She said she brought it because she sometimes gets scared in movies (we were seeing a comedy.)

After the movie, we grabbed some ice cream and drove the cousins home. My date invited me to kiss her at the door, but told me I should also kiss Pebbles so he wouldn’t be jealous.

4. Hooked up with a girl (she was 28) with dentures and she gave me a gum job.

5. We were going mini golfing and the dude picked me up wearing a full on tux.

It was so odd and everything about the date was uncomfortable.

6. The guy picked me up, and asked me where I wanted to go. I said, “Oh just somewhere kinda nice, not too fancy, but a good place to have a conversation. Maybe a coffee shop? And just somewhere kind of on the other side of town, I spend all day in this neighborhood.” He took me to a Hardee’s literally one block away. During the date he talked almost exclusively about his sexual fetishes.

7. The weirdest was when I was a college junior and dated a girl that was a classmate.

She wanted to have a “picnic” in a cemetery at a gravesite where her ex was buried (he had been killed in a crash 2 years prior).

I told her that I’d accompany her to visit his grave, but that picnicking and having a good time there somehow didn’t seem appropriate.

8. He took me to a supermarket. I don’t know why, but he had to start it somewhere, so it started there.

9. I was talking to dude on Tinder and decided to meet up with him for coffee one day. He only talked in impersonations of WWE wrestlers and then asked me to go to Wrestlemania with him and his entire family later that night.

10. I went on a date with a girl I met online. All throughout the date she kept looking over at me and then laughing, but not really in a mean way. After a while I called her out on it and she basically said, sorry but you really look like my brother. Then she shows me a picture and low and behold, he looks more like my brother than hers. I still can’t figure out why she agreed to go on the date in the first place when she could tell this was the case from my profile pic.

11. The one that ended with me asking if she wanted to go on another date some time and she responded with, “Um… I really like this guy Jason…”

SHE was the one who asked ME out!

12. Met someone online and we decided to meet in person for a date. It was awkward for the first few minutes, but then she just said, “I can dab if that will make it less awkward,” and then proceeded to do so. There was no second date.

13. First ever date, we watched Ted 2, half way in he shows me a picture of a dog sticking his tongue out with the text “kiss?” above it, and when I turned to him he gave me a peck on the lips and went on as if nothing happened.

14. Dated a woman who didn’t tell me she needed meds because she was psychotic. In the middle of dinner (at a restaurant) she got quiet and distracted. I asked if she was feeling okay. Apparently one of the voices told her I was a horrible person and she pulled a steak knife on me.

A customer was able to talk to her, and got her to put the knife down. The police were called, and she was arrested. I didn’t press charges, and about a week later, she sent me a letter with proof that she’s been in counseling for a long time, takes medication, and included a heartfelt apology.

15. I went on a date with a girl to a bar and grill. The girl just got set free from a bad relationship. The bartender was her uncle, the server was her sister, and her fresh ex-boyfriend was there on a date with another guy.

16. It was supposed to be a coffee date. I got there, on time, and he had already ordered and drank his coffee. I went up to get mine, he just stared at me from the table while I was ordering. The date itself lasted about 2 hours and I honestly can’t remember a single thing we talked about, because he wasn’t contributing to the conversation at all. There was one point where I was just staring at him and I remember thinking, “If he doesn’t bring up a topic of conversation in the next 30 seconds, I’m leaving.” Dude genuinely just stared at me. Maybe he was trying to communicate telepathically, I’m not sure.

When I tried to leave, he insisted that I stay. Why???? We haven’t talked about anything and it’s been 2 hours! Weird guy. I did end up going on a second date with him, but it was just as awkward. Called it quits after that.

17. In college, I went on a date with a dude who got all excited that we were on the same psychiatric medication. Like, I’m pretty sure he thought it made us soulmates or something. It was… different.

18. Met a girl at a coffee shop for a blind date in the early 2000s. We ordered, sat down, and started talking the usual stuff about ourselves. Things took a turn once we reached the employment portion of the conversation. Once I said that I was an animator she told me it was childish and left.

19. She spent the whole date on her tablet and phone, even though she asked me out. She is still single, she has not learnt.

20. Matched with a girl on a dating app who seemed super chill and sweet. Asked her out and we made plans to get dinner at a local burger joint.

We meet and after introductions she spent an entire hour bitching about how much her life sucks, how much she hates school, how annoying her managers at work are, how crazy her family is, etc etc. I get that part of dating is revealing your likes and dislikes, but for God’s sake don’t be a negative person who can’t quit complaining.

Felt like I had been emotionally catfished. Thankfully never heard from her again.

21. Went on a date with a girl who revealed that her hobby was buying dead little mice, doing taxidermy on them and then dressing them up in tiny little metal battle armor and swords to stage historical battles… using dead mice… that she bought online.

She showed me lots of pictures before the date ended.

22. Told a girl I was into granola environmental shit. She replied, “Me too.” We hit it off quickly. Anyway… She kept talking up how incredible her job was and that she taught a bunch of kids about environmental issues and how amazing this job was. Basically begging me to come check it out. So we picked a day and I took the day off from work. It had been a while since we saw each other so she decided it would be fun to send me real kinky texts about fun places we could sneak off to around her work as it was her fantasy. I was down, and I was getting in the mood myself.

I drive to her work, only to find out she works at a trash burning power plant and recycling center and on that day we’ll be giving a tour to a bunch of preschoolers. Throughout the “date”, basically every chance she could, she would try to get me turned on when no one was looking….there were about 20 kids and teachers right there! Meanwhile we’re walking through piles of rotten trash, or looking at machinery that could kill you in an instant if you stepped over a boundary line, or staring into a white hot furnace to see the burning trash. Therefore you walked around the dirtier you felt, which in a way was not surprising. I still had the worst blue balls in my life which in itself was questionable. Anyway… The tour ended, she took me in her office and well let’s just say it took three showers and a waive to a priest to feel clean after that.

23. Went on a first date where someone asked me why I cut my hair so short. I guess I could have lied or blown off the question, but I don’t like to start anything with falsehood, so I told him that I had chemo for breast cancer—that I’ll probably be completely fine now, and we absolutely didn’t have to talk about it. He asked me a few questions about the surgery (single mastectomy), and he said, “I wanna know which one it is, but I can’t look at your boobs NOW!”

I told him if he could guess which boob got the axe, I’d buy the drinks and appetizer. He won, and I never saw him again.

I’m positive I am the weirdest date THAT guy has ever been on.

24. My first dating app date. Starts off pretty good, we barely put in our dinner order and her phone starts blowing up. Her ex was drunk and causing a scene outside her apt. Her ex kept calling, then her roommate started and then the landlord calls threatening to call the police. We get our food to go and I take her back to her apt. Long story short, both her and her ex are crying messes, she goes inside, leaves me outside with crying drunk ex who starts telling me all about how he messed their relationship. Dude is way too drunk to drive, I end up driving him to his apt, Uber back to my car, realize my date took all the food with her. The joys of dating!

25. I was interested in this girl, and she kind of tricked me into a double date where she was dating another guy and had fixed me up with her sister. Being a good sport, I went along with it and it was awkward but okayish. But then she set me up with her sister again and this time it was just the two of us.

We went to the park. She had filled the trunk of her car with troll dolls (I mean dozens and dozens of them) and spent the entire date introducing me to her trolls one by one. (I should mention we were in our 20s.) She was getting frustrated and angry because I didn’t seem all that interested in her dolls. So sitting there, hands full of troll dolls, she exasperatedly asks me, “So are we going to have sex? Do you even know how to have sex?”

“Umm, not with you I don’t.” I said, and got up and walked home. There’s only so much one can endure while being polite.

26. I went on a 4 hour date with a woman who rides horses for a living.

The entire 4 hours she told me everything I could possibly want to know about horses and then some.

I learned so much about horses that I done forgot most the shit she told me.

27. I matched with a Chinese exchange student on Tinder. She asked me to meet her at her apartment, then we’d go link up with some of her friends at the waterfront. We’re texting as I’m on the way over, and she days she didn’t realize this was a date. Nonetheless, she asks me to pick up dinner for both of us on the way over.

I get to her apartment, and before I can even take my jacket off, she says, “So, do you have anything to say to me?” Presumably because I’d spent 15 seconds in silence. I offer her the food she asked for, she said she wasn’t hungry. I try to strike up a conversation, but she dead ends every topic I bring up. She starts texting, and making phone calls. She was speaking Mandarin, presumably, but I was able to make it the name of the place we were supposed to meet her friends. She said something about how plans might change because her friend needs help.

Throughout all this, I just sat by myself, eating my sandwich in silence. When I was finished, I asked if she just wanted me to leave. She said yes, then gave me $20 for dinner.

28. Dated a man who corrected my Polish, because his grandmother was Polish and she told him how to pronounce some words.

Mind you, I was brought up in Poland, went to school and college there, read a zillion books, saw a zillion Polish movies etc. But this guy was very condescending about my pronunciation of the few words he learnt from his grandma.

29. Went to the church of Scientology, roped in with promises of free food. We were on a date for Christmas. So, so odd.

30. When I was 15, a girl asked me to the movies. It was I Love You, Man. Her parents decided to attend too. Then one of the characters cursed like 10 minutes into the movie and the parents told us we were leaving. They took me right home and that was that.

31. The girl took me to a cemetery at night, walked me to a grave, explained that it was her cousin and that night was the anniversary of his death, then told me a long story about the time he raped her.

32. Third date with a guy from hinge. Started of completely normal- went to a pub for a few drinks. Pub closes. Guy invites me back to his.

We get back to his and have a few more drinks, he then asks if I’d like to smoke a joint. Hadn’t smoked for a few years but thought “hey it’ll be fine”. End up feeling very sick and unable to move. Guy doesn’t have a bucket or bowl so brings over the entire kitchen bin and places it next to me. He then suggests we watch a movie.

Guy puts on American Psycho and I sit there for the next two hours paralyzed and paranoid completely convinced he’s going to murder me.

Also he lived on a boat.

33. I went on a date with this girl from tinder. She “super liked” me and messaged first, so I was really happy to have someone interested. I asked if she’d like to go for a walk some time and she said she’d love to.

So we get to walking and like 5 minutes in, she asks if I have roommates. I said yes, I live with 5 people and tell her about a few of them. “Theres Max, Matt, Mark,…” “Wait, Mark Smith? I know him! What’s he been up to…”

So we start chatting about my roommate and she knows a lot about him. His family, the sports he plays, his girlfriend. Every time I try to move the conversation somewhere else, she brings it back to Mark. She’s not even pretending to be into me anymore, she’s just fangirling out over my roommate. “I just love him, his hair is always so shiny and he smells so nice!”. She spends the full 2 hours talking about him and asking all sorts of questions. I didn’t really know what to do, so I just boredly keep answering.

When we get back to our cars, she shifts gears again. “Hey, so I had a really great time. Want to go back to your place to have some fun?”. She’s really creeping me out at this point, so I tell her I have homework to do and maybe later.

I get back and tell Mark about the date and he knows exactly who she is. He picks up his phone and immediately calls the police. They show up at the house find the girl outside in the back yard and arrest her for violating a restraining order or something.

It turned our she was super unstable and had stalked my roommate since they went on one date almost a year prior. She recognized from photos she had of him and used me to find out where he lived.

34. I dated a dancer one time. We meet up. She looks phenomenal. Terrific outfit, nails, brow game, makeup. Really earned attention to detail points. We go to the best steakhouse in town. Order a couple of surf n turfs. Grab coldies. It’s going well. Food comes. We dig in.

This chick ate like a complete pig. Like watching Daryl Hannah in Splash. Bitch had lobster in her hair, down her dress. It was almost impossible to watch. I bowed out at the earliest possible moment.

35. Guy starts showing me pics of his super super old cat. Which is not a problem, I love cats, I told him that I also have a cat.

But then he starts explaining… He recently adopted this elderly cat because in cat years he calculated that it would be his mother’s age. He named it after his mother. Full name. And his mother had just died.

I stayed real calm and kind about the whole thing, people cope in their own ways, but that’s a weird red flag amirite?

36. This guy I matched with on Tinder was bragging about his dance moves so we went to this bar/cafe type place near where I live. Turns out he can’t dance for shit and was just doing some weird side-step over and over again, then he whispered “Want to give them a show?” in my ear and tried to make out with me. I barely said 5 sentences to this dude.

37. I had a girl bring me to a bingo night. At a Shriner’s hall. We were the youngest people there by a quarter of a century at least. And we were both pretty terrible at it.

38. Within 5 minutes of sitting down to dinner, the lady whipped out a handwritten epic poem (at least 50 pages) about how she had broken up with her last boyfriend because he loved weed. She then proceeded to read the poem aloud in a crowded restaurant.

39. My first official bf took me to his Christian church for our first date. and it was one of those scary churches where people throw themselves on the ground sobbing and convinced the lord is in them. Sure take the pagan to a Christian church.

40. I went on a first date with a dude a few months ago and halfway through dinner, he pulls out a folder with a thick stack of paper in it and slides it over to me.

Turns out it was a contract for dating and eventually marrying him, listing all the requirements he had for an SO. I got through about two pages before I laughed, stood up, and left. TC mark

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About the author
January Nelson is a writer, editor, dreamer, and occasional exotic dancer. Her work has appeared on Facebook, ... Read more articles from January on Thought Catalog.

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