41 Men And Women Share The Most Insane Dates They’ve Ever Had To Suffer Through

8. Date needs 20 BUcks, is scared of being alone with a woman

We had been talking on the phone for about a month already. He tells me his car is booted – outside of his house. He had a long drawn out story about how he could not get the boot removed. His dad was staying with him and he thought would be able to use his dad’s car but now he can’t. So I go to get him to go somewhere to eat. He starts panicking saying, “oh great, now I’m in the car with you and I’m going to get accused of rape or something.” I asked him what the hell he was talking about. He just kept rocking in his seat anxiously, worried that he would be accused of rape. I drove to the nearest area with food and asked him where he wanted to go. He said he had no money and wanted to go home. So I took him home. Then he asked me if he could borrow $20. I don’t know why, but I gave it to him. After this, he called me repeatedly and I ignored his calls. He texted me asking why he was “not good enough for me to date.” I kept ignoring him.

Fast forward 3 years. He is on a dating site I am on. He messages me but does not remember who I am. He tells me that a year ago his long time girlfriend passed away – the one he had lived with for 10 years. So, he was not staying with his dad, and he was freaking out because he lived with his girlfriend when he met me, right outside of his house. I called him out on it and he tried to pretend I had the wrong guy. But he had the same name and worked at the same place, and looked like the same guy. Very bizarre.


9. A Friend Plays Matchmaker

My freshman year in college I had a crush on a girl from my high school. When I asked her out, she informed me that she only dated women (I am male). She insisted that we were still friends, she just didn’t roll that way. She offered to be my wingman and I gladly took her up on the offer.

A few weeks later she had set me up on a semi-blind date with one of her friends (we’ll call her Monica). The three of us met at Arby’s (because we were fancy) and my friend tried playing matchmaker.

“PimpNinjaMan loves theatre and so do you, Monica!”

“Monica loves music and so do you, PimpNinjaMan!”

The date was going fine, so my friend decided to leave Monica and I alone. We talked a bit more and decided to go see a movie. I didn’t have a car at the time so I hopped in Monica’s passenger seat and we went on our way.

That’s when shit got weird.

About two minutes after leaving Arby’s, Monica receives a phone call. She says it’s her roommate and she needs to answer it. She picks up the phone and I hear a man’s voice. I was a bit surprised, but it’s not too unusual for a girl to have a guy for a roommate.

Monica and her “roommate” get into some kind of argument, and she pulls over to a gas station. Another car pulls in right beside us. Again, I didn’t think anything of it at the time.

Monica turns to me and says “I need to go talk to my roommate. Just wait here for a minute.” I assume she just wants to be on the phone in private, but what happens next will shock you! Monica gets out of the car and goes to talk to the driver of the car that pulled in next to us.

This is where I start to freak out. What are the odds that her roommate happened to pull up right beside us?! I hear a bit of yelling and then I start thinking about an escape plan.

At this point, Monica opens my car door and says “Hey, I’m really sorry to do this but my roommate is going to have to take you home.”

Now, this is the part of the movie where someone in the audience screams, “Don’t you go with him, now! That’s how you get killed! White people always going with the strange man thinking everything will just be a-okay!” I wish I could say I got smart, said, “No thank you, I’ll just walk” and went home.

But I didn’t.

With some combination of confusion and curiosity, I get out of Monica’s car and head into the passenger seat of this stranger. We’re in my hometown, so I know if he goes any direction he’s not supposed to I can just bail out of the car and run to freedom.

The guy was pretty big. I was 6’2″ at the time and he was significantly bigger than me, if that tells you anything. I don’t remember his name, but we’ll just call him Ross. Anyway, Ross starts driving back to my dorm and we’re sitting in awkward silence for most of the trip.

Eventually, he says, “So how do you know Monica?”

I knew something fishy was happening, so I wasn’t about to say we were on a date. I just say “Oh, we have a mutual friend!” and hope Ross doesn’t get suspicious. He just nodded his head and kept driving.

Apparently, Ross was resolving some anger in his head because out of nowhere he starts talking as if we were in the middle of a much more personal conversation.

“Yeah…. A lot of people at our church are upset that Monica and I live together. I think they’re just assuming we’re having sex all the time or something. It shouldn’t even matter since we’re engaged, but it’s still annoying to hear stuff like that, you know?”

I just nod my head as I realize what just happened. Apparently, my lesbian friend set me up on a blind date with an engaged girl, and her fiance came and picked me up to take me home.

I was silent the rest of the night. I told Ross the wrong dorm so he wouldn’t know where I lived, and I got out of the car and just walked around campus for a bit. It was definitely the strangest date I’ve ever been on.


10. Spontaneous Lactation

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.



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