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13 People Share The Strangest Dates They’ve Ever Been On

A first date is like a job interview—it’s awkward, uncomfortable, and all you really want is for things to go smoothly and for it to be over. Tbh, I’ve had my fair share of not-so stellar first encounters, but none could quite compare to the deeply disturbing dates that these Redditors have been on. It’s a wonder that they haven’t given up altogether.

1. Leucoch0lia should probably avoid any further contact with that guy.

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.

2. arrrjen was just a pawn in an evil revenge plot.

Got asked out by a girl I knew and was sort of interested in, but didn’t really know all that well. We went to an open air jazz concert, not really my thing but sure. Once there she immediately was all over me (hugging, sitting on my lap etc.) Things were going great (or so I thought) It was at that point when things started getting weird: several band members where giving us strange looks from stage, while playing their jazz music. One piano player was mouthing things in our direction, but I couldn’t make out what he wanted. People were rude to me for no reason whatsoever while getting drinks. Long story short: my date knew just about all people there and wanted to get back publicly at her (very large) boyfriend for cheating on her. Don’t hate on me jazzfucks, I’m just an innocent sucka! Awkward ending: I met them both later that evening at the train station and she pretended not to see me.

3. Thieves don’t make for solid partners, sprout272.

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

4. animalcollectivity‘s date is never growing up.

I met a guy from OKCupid. The first time we met up in a public place and just had a casual chat. It wasn’t a horrible date, but it wasn’t very memorable either. I decided to give him another try because it could have just been nerves. The 2nd date he invited me over to his place… I knew he lived with his parents, but i kind of assumed they’d be away.

They weren’t away. They kept coming into the loungeroom and giving us iced tea and chips whilst he played XBox in his trackpants (no shirt) and i sat there awkwardly watching. He didn’t really speak much to me. It was 11pm, and he was in his 30s.

5. kalvinbastello will never see pigs the same way.

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.

6. Run, officialswitchfoot RUN.

The first time I ever used Tinder was also my worst experience with Tinder. The date itself was fine – a little stiff – but fine. Typical questions like what are you studying, where did you grow up, etc. We ate dinner and I didn’t plan on meeting up with him again.

The next day I got a text from him saying, “Hey.” I text him back “Hi”. He asks me what’s up, I say not a whole lot what’s up with you…

End up getting a HUGE paragraph back talking about his creative process for writing (and trying to direct) a specific type of porno where women crush rats and tarantulas between their breasts. WHAT THE FUCK

7. blueberryeyes24 should probably just avoid spicy food altogether.

While I was rebounding from a 5-year relationship, I went on a sort-of date with this weird dude from my community college who kinda stalked me, but was pretty much harmless. We went to buffalo brothers, and he ordered 2 dozen wings with their ludicrous sauce.

If you’ve never had this sauce, picture the spiciest thing you’ve ever eaten, and multiply that by 1,000. I sat and stared in horror as he began eating. He had tears, snot, and sweat rolling down his face and dripping onto the table, but I guess in some attempt to impress me, he finished every single wing.

He immediately excused himself to the bathroom and vomited everything up, came out crying, and took me home. He did pay for dinner, though, which was nice. Once we got to my house, he tried to kiss me. Noooooope.

8. 208th may have gone on a date with a future serial killer.

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.

9. How did you not vomit, 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.

10. Sebws got very lucky with that turn of events.

Once i talked to a girl on tinder that i hit it off with pretty well, and we made plans to meet up later in the weekend. We’ll call her Sarah.

The next day though, another girl that i’d talked to, that we’ll call Sophie, told me she’d be out at a bar close to me. She told me to come join her, and bring a friend. So i brought my roomie, and went to meet Sophie.

As we got to the bar, i spotted Sophie sitting there with another girl, whose back was turned to me. Went up, gave Sophie a quick hug as i sat down next to me, and motioned for my buddy to sit on the other side with the other girl.

It was only then i actually looked at Sophie’s friend. First noticing the intense stare i recieved from over the table, i realized the girl was Sarah, the girl i had made plans to meet up with the following day.

I could see she was equally taken aback as me, and for what felt like an eternity we sat there with the biggest deer-in-the-headlights-look before the silence was broken by Sophie, saying “Hey Sebws, this is my bestie, her name’s Sarah!” Which led to us nervously shaking hands, exchanging names, not knowing what else to do.

Already having shook hands as strangers, neither of us really knew how to proceed, not wanting to mention the elephant in the room, since Sophie and my buddy had no clue what was going on.

It actually did go allright in the end, my roomie and Sarah ended up talking, and hitting it off. It seemed we’d reached a silent, yet mutual agreement not to mention the glowing mammoth in the room in the room.

In the end, the girls actually ended up going back to our flat with us, spending the night.

I only told my roomie the reason i had looked so confused, after they had left the following day. But yeah, that was such a strange date, which somehow worked out.

11. OminousPumpkin probably should’ve called the police.

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.

I got lucky. They moped and took me home. I was terrified. That was horrible.

12. bitterbillsfan may never know the truth.

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)

13. shinyhappycat definitely did not see that coming.

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.

What do you think?


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