People Shared Stories Of The Strangest Dates They’ve Ever Been On And WOW

By 04.19.17

Dates can go south in a hurry. They often do when you’re matched up with a total stranger. I wish I could tell you about the weirdest dates I’ve ever been on but they involve me drinking too much and waking up without a clue where I am, in a neighborhood I’ve never seen, and with a girl whose name I can’t remember. But this isn’t about me, this is a collection of stories from people who have shared details about the weirdest dates they’ve ever been on. What does this mean for you? Try and avoid these situations whenever possible and you’ll do much better in the dating pool (via AskReddit):


joceapotamus:
Wasn’t my date, but I had gone home with a guy I had been seeing and when we got there his roommate was curled in a ball on the couch looking pretty shaken. We asked him what was wrong and it took him awhile to get it out, but he finally told us what happened:
He took a girl home from the bar and they started drunkenly tearing each other’s clothes off as soon as they got through his bedroom door. She said she was self-conscious though so she wanted the lights off. He switched them off and they started fooling around. She starts going down on him when all of a sudden, the guy notices this horrible smell. He mentions it but she tells him to just ignore it, he’s probably imagining things. Finally the smell is too much so he switches the lights on. That’s when he sees it.
Shit. Literal shit all over her and all over the bed. He is completely dumfounded, doesn’t know what to say or do so apparently all he yelled was “SHIT!!!!” She grabbed all her clothes and ran out of the apartment crying without saying a word and, presumably, still covered in poop.
He threw his bedding out, took an hour long shower, and refused to go back into his room. Pretty much killed our night too. To this day I still wonder what on earth happened- was she into it and was hoping he would be too? Was it an accident and she decided to just go with it? I don’t know which scenario is more horrifying to be honest.


bitterbillsfan:
It’s 2001, so VHS & chill at this girl’s dorm room.
My first time over there, and there is this giant bear on the bed. Like, got the softball in the milk jug at the carnival first try tier bear. It occupies 50% of the surface area.
I say “whoa, how’d you score that bear?”
Her: “I don’t know…”
Me: “Wot?”
Her: “I don’t know”
A few minutes go by.
Me: “You don’t know?”
Her: “Yeah.”
Me: “Ok, look. It’s ok if it’s from an ex. I don’t care if you stole it. I’ll believe almost anything you tell me at this point. But there is no way in hell you’re going to tell me you don’t know where that giant bear is from. I had a stuffed dinosaur 1/4 that size that I got when I was 6 and I could tell you every detail about how I got it.”
Her: “Well good for you. But I don’t know how I got it. Are you going to be able to let this go?”
Me: (looks at bear, bear stares back, eyes full of secrets) “I don’t think I can” (walk out)


brooke_girl:
Had a good friend in uni who disappeared overseas for a year after we graduated. I stayed there to study and teach, and one day I got a text from a number I didn’t recognize saying “hey, it’s Joe from business school, want to catch up for a coffee?”
Hadn’t seen him in ages so I said yes very enthusiastically. I walked into the coffee shop at the right time, look around for Joe, and there’s Joe from business school. A different Joe from business school.
I couldn’t walk out because he’d already seen me, so we chatted politely for an hour and we’ve never talked since.


wellman_va:
Hot girl from class randomly walked into my dorm room, the door was normally open during the day. She was in the building visiting a friend and saw me playing guitar so she came in and started flirting. She asked me to meet her at a near by bar that night at 10 so I agreed. I get there at 10 and she introduces me to her boyfriend. I finished my beer and went to the bar my friends were at.


208th:
Matched on tinder with a guy who decided that a great story to tell in detail on our date was about the time he fisted a lady and tore her up so bad inside that she was bleeding profusely and had to go to the hospital to get stitches.
After he was done telling the story, he told me he was glad I told him I was super squeamish, because now he wouldn’t try to show me pictures of all the blood he had saved on his phone. He also said he had been on well over 100 tinder dates, and I had managed to land in his top 10.
I never talked to him again.


i7xx:
Well, this one time I took my date to dinner at (what seemed to be) a front for some type of illicit activity.
We had just moved to a new area, and we wanted to check out the local shops and restaurants. While we were wandering, we stumbled into a tiny Italian place. Back home, the small hole-in-the-wall restaurants always have the best food, so we were excited to give it a shot. Big curtains were covering the entry windows, so we had no idea what was inside until we trudged through the door.
Inside, we were met with emptiness and silence. We both immediately thought the store was closed, and I spun around and searched for the store hours posted somewhere on the door. While I was looking, we heard a heavy THUD as a young woman barked “I’ll be right with you!”
She appeared, greeted us confusingly, and asked us ‘what she could do for us’. Which, looking back, is probably a red flag. But we were naive and hungry, so we said we were there for dinner. She looked puzzled, but motioned us to follow her to a booth right by the entrance.
She then disappeared into the back, and we heard a muffled conversation between our hostess and a man. The consensus was basically they were not prepared for us, or didn’t know how to proceed. I asked my date if she wanted to split, but she insisted we stay for the story.
The square shaped balding man burst through the kitchen door with two glasses of water for us, and in a very loud and deep voice he explained that it was his birthday, and we would eat what he felt like making us. We whole-heartedly agreed.
We waited around thirty minutes, and he again returned with three large bowls of spaghetti and meat sauce. He placed two bowls in front of us, and one next to me for himself. He sat with us and ate. We had light and awkward conversation with him during, and he kept asking us jokingly if we were cops or with the health board. He was incredibly nervous about us, so my date kept cracking corny puns or awful jokes because he would foricbly laugh at anything designed with humor. We talked about our lives, the cities we’ve lived in, our pets (he had a teacup Chihuahua named Princess) and his wife.
He decided we were good people, and didn’t change us for the meal. We wished him a happy birthday, he hugged us, and we went on our way. Easily the best spaghetti I’ve ever had in my life. The restaurant, unfortunately, no longer exists.


kalvinbastello:
Met a girl online, talked it up, and while she seemed a bit immature, thought heck, why not? She casually mentioned she really liked pigs. What she meant to say was she was obsessed with pigs. OBSESSED.
Go to one of the best restaurants in the area for a first date (bad idea). Sometimes pictures are from someone 10 years prior, or the person hides things, etc. But that wasn’t the problem. She looked just like her pictures. But I didn’t even have to have seen her first, because everything else gave it away.
She came in a giant T-shirt that had a sparkly pink pig on it. Earrings? Pig earrings. Bracelets? Yep, pig bracelets–I swear her dad might have been Homer Simpson. She had this headband on with a little pig on it. Her shoes? Yep, pigs on the front of the toes! But best of all? She had a GIANT (or at least it seemed giant) pink purse with the face of a pig on it.
You could not stop seeing it once you did. And I’m sure everyone else in this nicer/classier restaurant saw it too. I felt overdressed with her but under-dressed with every other couple there. It was beyond embarrassing. For some reason which I have to convince myself was politeness not stupidity, we still had dinner. But Reddit, it was the fastest damn dinner I’ve ever had at a sitdown place.
I practically blurted out something about how “oh, you really do like pigs…” which she started giggling (oinking?) and going on about how everything she has is pig themed. Then she wouldn’t stop, and it became the dominant part of the conversation. There were a dozen other things that made it a train-wreck, but these were the clinchers to a solid 0/5 date. I remember afterwards consoling with a friend of a friend, because I had to tell someone; and then I promptly buried this as my worst date.
TL;DR: Girl was obsessed with pigs but ironically no porking at end.


Leucoch0lia:
Internet date; at a bar; first time meeting the guy. He tells me over a bowl of eggplant chips that he’s so good in bed that the last woman he boned spontaneously lactated from the mind-blowing pleasure of it all.


OminousPumpkin:
I was a waitress and I had a table of 2 guys. One was very cute and flirting with me and we exchanged numbers. He asked me out and I said yes. I didn’t really go out much and he didn’t tell me where we were going out what we were doing. Me being young and dumb at the time thought that would be exciting. So he drives me a pretty good way from my house and we go to an elementary school. I was really confused. Apparently he was a basketball coach and they had a game that night.
So at this point I notice I have no reception on my phone and I really wanted to leave but I thought maybe we were going somewhere fun afterward so I gave up trying to call someone to rescue me. I sat and watched this game right next to this dude’s mom. Yeah this was going well.
Finally the game ended and we go to get in the car and his friend from the restaurant gets in the front seat making me sit in the back. I am super uncomfortable with this and I ask what’s going on. They basically tell me they want to run a train on me. Nope. Fuck that. Take me home now.


sprout272:
I’ve posted this before because it’s so weird. I went for a meal with this girl I met through a dating app and it was going really well. We started talking about movies and then we decided to go to the cinema to go watch Inception. She said there was a cinema nearby but I didn’t know the area at all, so I used the GPS on my phone and she held it and directed me. Once we got there we started walking inside and I realised I didn’t have my phone in my pocket. I said I must have left it in the car and started to walk back to get it. She was trying to get me to leave it and saying we would miss the film but the phone was only about a week old so I was really paranoid about it. We checked the car for about 10 minutes but we couldn’t find it. I asked her to check her jacket and her bag but she said it wasn’t there. A couple parked next to us so I asked them to ring my number because I couldn’t find it. It started to ring and it was obviously coming from my dates handbag. She took it out and said she must have missed it. I thanked the couple and locked my car and as I turned back around she was walking the other way. I ran to catch up and asked what was going on but she was very dismissive and was barely talking. That’s when I realised it wasn’t an accident and just left her to walk home alone


Amecha:
Got set up on a date with this pretty awkward guy, he picked me up in his car which was sort of cool considering we were in high school but oh my god he was a nervous driver. So nervous in fact that he accidentally ran a red light, lost his shit and ducked into a residential area to sit at the end of a cul-de-sac freaking out thinking the cops were coming. I tried to explain that if a cop had seen him we’d have already been pulled over but dude was too freaked out. I don’t even remember anything else about the date, just that. It was uneventful and I never really talked to him again because we had nothing in common.


ModelMakerPro:
This was in high school.
Asked a girl out to coffee at a local coffee shop. She says yes, seems excited.
Show up at the agreed upon time only to see that she’s brought a bunch of her friends. Okay, whatever, I guess this isn’t a date now.
Despite the weird situation, I have fun. Then I get a text from my brother that he’s going to be nearby and could pick me up in his car. Tell the girls that I need to get going. They stop talking and just stare at me. Nervously, I explain that my brother will be there soon. They don’t say anything. I hear my brother honk his horn outside the coffee shop and awkwardly slip out of my seat and head to the car, saying goodbye to the still silent and staring girls.
Then, a week or so later, I get a call from the girl I has asked out. She’s furious that I stood her up, apparently. Confused, I apologize and explain that the whole thing was really weird. She starts to laugh at me and informs me that I’m actually on speaker phone and all her friends (the ones from the coffee shop) are there. They all laugh and make fun of me for being confused and apologizing.
I just hung up and never spoke to them again. I never figured out what their angle was. Prior to the “date” me and the one girl got along well and she definitely seemed to be attracted to me.


b8le:
Have had 3 separate dates, with 3 separate women that all turned out to either be christian revival meetings or younglife.
c’mon people


AlternatePhysics:
Okay. I have never shared this story online before, but here goes.
I was going to have a second date with this girl. She knew of three parties happening on the same night, so she suggested that we hit all three. Sounded good to me, so off we go.
At party one, her best friend from college is there that she hasn’t seen in four years. They immediately run off together, and I’m left with the friend’s boyfriend having a drink. I think to myself, this is no big deal. She hasn’t seen her friend in a long time, and the night has a lot more to go. She comes back after a while and suggests we head on to the other party. Great!
Arrive at second party. My date immediately runs off with some other friends. Like, “Tim, oh my god, how are you doing,” and dashes across the party to find him. I slowly follow behind, but then they keep scurrying on to talk to other people without the girl making it clear that she wanted me to come. I feel really awkward because she doesn’t introduce me or say anything about me. I’m just an awkward guy there that no one knows. I get tired of that and go to the bathroom, where I find that the door has been ripped off its hinges. I find a screwdriver and fix the door before using the bathroom. Fast forward 30 minutes, my date finds me and suggests we go to the final party. But this time, her friend Tim is going to join us. Okay…
Arrive at third party. As soon as we walk in the door, Tim says he needs cigarettes, and the girl and Tim run out for cigarettes and leave me at this new party with all these other people I don’t know. They are gone for 45 minutes, by which time I decide that this date isn’t working out and I should just go home. When my date comes back with cigarettes, I tell her I’m leaving and she FLIPS OUT. She starts screaming at me in front of everyone about how she was going to have sex with me later and how I ruined everything. Then she proceeds to scream, “you’re not leaving me; I’m leaving you,” after which she bolts out and slams the door.
Then everyone at this other party, whom I don’t know, is staring at me while my date, who brought me there, has abandoned me.
Someone eventually comes and offers me a drink. I stay for another hour and laugh it off with the people at the party. Am still friends with some of those fine people today.


shinyhappycat:
Met a girl online, decided that we should meet for a date. (I’m female BTW – this sort of matters). I arrived in a strange town that I didn’t know so I relied on her to show me around. She took me to a youth LGBT group, I thought we were staying, didn’t mind – it’s a bit odd but I was newly “out”.
Turns out it was just a chance for this girl to show off that she did, in fact, have a date (they didn’t believe her apparently) and I existed. It was really awkward. When the youth group leader came in, she stood up, grabbed my hand and said “later bitches” and we walked out.
Went to a bar for a drink, and then on for some food. It wasn’t going well, she was very odd, but I was new to all this, and in a town I didn’t know. Once we’d eaten she said, “oh I just need to see a mate who’s staying at xyz hotel” – fine, went to see this friend. Oh no. She’d booked a hotel room for us for the night! Yeah – I left pretty quickly after that. I may have been inexperienced, but I wasn’t about to be tricked into a night in a rough hotel with an odd little lesbian. No thank you.


People are so goddamn weird.

Well, bros, that wraps up the coverage from my end but if you want to keep on reading these AskReddit stories you can CLICK HERE to see that thread in full!


TAGSAskRedditawkward datesDatingfirst date

Join The Discussion