Single People Share the Weirdest Dates They’ve Ever Been On


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. Mystery Bear

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.