14 Single People Share the Craziest Dates They Ever Endured

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There are a lot of weirdos, freaks, and geeks out there. Which makes dating a risky proposition a lot of the time.

The pickins are slim, people, so when you get a good one, hold on for dear life.

These 14 AskReddit users definitely DID NOT have any interest in continuing the romance with these strange folks. Take a look.

1. Good ol’ Joe

Had a friend in college named Joe. He disappeared overseas for a year after we graduated. I stayed here to study and teach. 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?”

I hadn’t seen him in ages, so I said yes very enthusiastically. I walked into the coffeeshop at the right time, look around for Joe, and there’s Joe from business school. A different Joe from business school. A guy I barely knew.

I couldn’t walk out because he’d already seen me, so we chatted politely for an hour and we’ve never talked since.

2. No kiss for this one

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 a wing joint, and he ordered two dozen wings with tons of crazy 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. He came back 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.

3. VHS and Chill

It was 2001, so I was VHS & chilling at this girl’s dorm room.

It was my first time over there, and there was this giant bear on the bed. Like a ‘got the softball in the milk jug at the carnival first try’ bear. It occupied 50% of the surface area of her bed.

I say, “Whoa, how’d you score that bear?”

Her: “I don’t know…”

Me: “What?”

Her: “I don’t know.”

Me: “You don’t know?”

Her: “Nope.”

Me: “Okay, look…”

Me: “It’s okay 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 you’re going to tell me you don’t know where that giant bear is from.”

Her: “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.”

I got out of there and never looked back.

4. Waste of time

This cute 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 nearby 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 made my escape. No idea what that was about. Glad I didn’t stick around to find out.

5. Online dating is fun

Met a girl online, decided that we should meet for a date. (I’m female BTW – this sort of matters). I arrived in her strange hometown. I didn’t know my way around, so I relied on her to show me around. She took me to a youth LGBT group. I 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 that I existed. It was really awkward. When the youth group leader came in, she stood up, grabbed my hand and said “later idiots” and we walked out.

We went to a bar for a drink, and then on for some food. It wasn’t going well. She was very full of herself, 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 a hotel” – fine. Only it turns out there was no friend. 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 someone I didn’t like.

6. Creep

I was a waitress and I had a table of two 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 or 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.

At this point I noticed I had 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. We went 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 tell me they want to “share” me. Nope. Take me home now.

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

7. Conversion

I have had three separate dates, with three separate women who all turned out to be Christian evangelicals trying to convert me.

8. Mobbed up

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.

A woman’s voice barked “I’ll be right with you!”

She appeared, greeted us, and asked “what she could do for us.” Which, looking back, was 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. I asked my date if she wanted to split, but she insisted we stay until we figured out what exactly was going on.

Suddenly, a square-shaped balding man burst through the kitchen door with two glasses of water for us. In a very 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 made light and awkward conversation with him throughout, 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 jokes because the man would foricbly laugh at anything he took for humor.

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. Also… it was definitely a mob front.

9. Paranoid

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 mind 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 have been pulled over, but this dude was too panicked to listen. I don’t 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.

10. Tinder time

We met on Tinder, hadn’t talked for too long but I thought what the hell? I need to get out more. The first thing he said was, “Oh wow, you’re so pretty!”

Two drinks in, we’re having an awkward conversation, and he’s buying me double G&Ts instead of the singles I’m asking for. Mid-sentence, he grabs my face and says, “Sorry – I just need to get this out of the way.”

Then he forcefully sticks his tongue down my throat. I didn’t really know what to do because I didn’t want to cause a scene.

I said I needed to look up the time for the last train. He said, “no it’s fine you can stay at my place!” He begs, saying he’ll sleep on the couch, he just wants to get to know me better. I said no. He huffs, very briefly, and then cheers up and tells me he’ll look up the train time for me “like a gentleman.”

He says it’s at 1 AM. I said that’s late, is he sure? He gets all tense and says, “What? Don’t you believe me!?” I smiled and said, “of course not.” I excused myself to the toilet and checked the times on my phone. (The last train was actually at 12: 15. Lovely.)

I went back to my seat, told him I’m getting an uber, goodbye. He tried to beg me to stay, loudly and embarrassingly, so others could hear (hoping I’d get so embarrassed I’d go home with him I guess?) and even pretended it was his birthday and yelled to the bar that he was protecting me by taking me home because “taxi drivers can be rapists.”

I told him that I was going home; he loudly asked for a hug and tried to grab my boobs.

11. A great guy

This guy I met online was half an hour late for the date. The first thing he said to me was: “You’re too tall. You’re taller than me.” I’m 5’5, and I was wearing flats – nowhere on his profile was his height listed, never mentioned anything about it. He said he’d buy me a drink for being late, so I figured I’d get a beer out of it.

We chatted for a bit about our jobs and school and whatever. I check the time, and realize I have to catch my bus back home – I lived in the suburbs with my parents at this point. He says “Okay, I’m coming with you.”

“Uh, no.”

“Well, I guess you can come back to my place. My roommate is there though.”

“I’m not coming home with you.”

“I bought you a drink! You owe me! …Whatever. You’re not even that hot.”

“I am not going to sleep with you. I’m going home.”

He just stalks off in the opposite direction. Then, amazingly, I get a message from him later.

“Look, I’m sorry. You’re a great girl and I enjoyed our time together. But this just isn’t going to work out.”

Um, yeah. I thought that was obvious.

I came across this dude on another dating site later. His profile was a picture of his abs; his secondary pic was him ‘sexting’ with a girl. “So you know I can satisfy the ladies.”

Good luck with that pal.

12. An OK Cupid entry

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 second 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 living room and giving us iced tea and chips while he played XBox in his track pants (no shirt) and I sat there awkwardly watching. He didn’t really speak much to me. By the way, we were both in our 30s.

13. Porn bar

Went out with a customer from my work (I was a bartender, so I got hit on quite a bit, but this was the first time I’d actually gone out with someone). He took me to a bar near his apartment. The place was really dive-y and a little too hipster for my taste, but whatever. We were having a great time talking and enjoying some drinks, when I suddenly notice the TVs behind the bar. Instead of playing sports or the news, they’re playing old porn movies. I brought it to his attention, and he kinda just shrugged it off and said it was normal for this place

14. Weirdo

I went to the movies to watch Inception with a girl I met online. Once we got there we started walking inside and I realized 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. A couple were 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 date’s handbag.

She threw the phone back and literally ran away.

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