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

23. The Dumpster Diver

I went on an OKC date once.

The girl and I drove past a mattress and box spring hand wrapped in plastic.

I drive a truck.

She asked and then insisted that I stop and get the box spring/ She wanted me to put it in my truck and then help her put it in her second story walk-up apartment.

I politely said no, I do not think that is a good idea. That there is a pretty solid chance of bed bugs because sealing an item is what you try first when you have those nasty little things. She was having none of it.

I refused. She started crying, telling me that I don’t know how it is to not have things and that it is easy for someone born with a “silver spoon in their mouth” to write off a free box spring. She didn’t know me at all and made these assumptions based on who knows what.

It was hard to hear since I came from absolutely nothing and worked my ass off to get to where I am.

We pulled into the restaurant, she settled down a bit. We ordered our food.

She answered a phone call at the table; It was a friend that had an extra ticket to a festival.

She reeeaaaalllyyy wanted to go but had just started a job serving food at a restaurant.

I suggested that she not call her boss and ask for the days off. I worked in the restaurant industry when I was younger and I knew that her supervisor would not let her call off from her fist weekend. She called her work anyway. She started crying when her boss said “no.” I felt bad for her boss, not her. Her boss fired her on the spot.

I paid the check with both of our meals still steaming and untouched. On the way back to her house we reached a stop sign. She jumped out of my truck and ran towards a trash pile. She came back with a hand day-glow painted end table and threw it in the back of my truck.

When I got to her house I said nothing. Just put it in park and hit the unlock button.

She then took both of our to go bags and ran off with her “new” end table.


24. Choo Choo!

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.


25. Joe, From Business School

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.



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