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

36. Porn On All The TVs

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 or something, 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.

I actually thought it was pretty cool and this joint became one of my favorite bars (more for the cheap alcohol than the porn), but it was still a really strange place to bring someone on a first date.


37. High School Is Fucking Bonkers

Some back story, I had a guy friend in high school who wanted to date me and I didn’t so I said no. He then told everyone I was a slut and did drugs and what do ya know, tons of guys turned out to have had sex with me (not really true). Anyway, I somehow got a reputation for being a slut without actually doing anything.

So this guy who is a big nerd asks me out on a date and I said sure because he was cute and I kinda liked him. I had been to his house before so after we go to a decent dinner we go back to his place to watch TV. I should have known, but I just assumed this guy was really poor like me and couldn’t afford to do more. So we get there and none of his family is home, and as soon as we walk in he is leading me to his bedroom not even smiling, with a really solemn look on his face. I just kinda laughed and told him I don’t really have sex with everyone. I was expecting maybe he would act like that wasn’t his intent, or he would be mad, but he just straight up started crying. The rest of the night was spent talking about how shitty high school is and how much pressure he felt to lose his virginity but didn’t even like me that much. He had a girl he actually liked but wanted to be “experienced”. Then we watched Mystery Science Theatre.

He is still one my friends today. But it was definitely a weird date.


38. Christian girls

Have had 3 separate dates, with 3 separate women that all turned out to either be Christian revival meetings or Young Life.



39. Girl Hooks up Jealousy Trap

Hot 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 went to the bar my friends were at.


40. Super Douche Makes An Appearance

Tinder matched with a guy who 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″, 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 made that clear long before we even met up.”

“I bought you a drink! You owe me!”

“What the hell? I owe you nothing.”

He puts on this super angry face and starts negging me.

“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. I get a message on Tinder later.

“This isn’t going to work out.”

Uh. No shit. Lol.

Came across this dude on Bumble later. His profile pic was a pic of his abs; the secondary pic was him ‘sexting’ with a girl. “So you know I can make girls cum”.

Lmao. Good luck pal. Good luck.



Michael Che (comedian and anchor for SNL’s Weekend Update) ruined one of my first dates! I go to a lot of standup around NYC and I happened to see him trying out material at two different free shows in the same week. He was doing this crowd material bit about porn where he would pick a guy in the front row and corner them and ask them what they searched for when they looked for porn. The first time I saw him doing it he just would not let up on this poor guy, the guy didn’t want to answer and kept saying “I don’t know” or “I’m not sure” but Che kept asking “come on, man, I KNOW you know. What do you mean you don’t know?” The guy never relented and said anything out loud but Che kept pressing him for seriously the entire show, like he kept going back to this one poor guy. Cut to later in the week, I’m taking an OkCupid date to a standup show, I sit in the front and Michael Che turns out to be the surprise headliner. The second I see him on stage I fucking know it’s gonna be me, I know he’s gonna do the bit again and I’m sitting front and center. My brain is racing trying to think of a good way to get out of this awkward situation, “don’t say BDSM don’t say BDSM” (this was a very casual date and I had not been speaking to this poor girl for very long plus I’m already a weirdo). Within like 30 seconds he turns to me and asks “what about you, sir, what do you type in the search bar when you look for porn?” and I think “okay self just say the most innocuous harmless kink possible.” I stall for a second with a “who me?” and he repeats the question, so I blurt out without thinking “Redheads!” Whew, fine, I’m in the clear. Awkward situation handled. I forgot that my date was a redhead. Of course, he immediately picks up on that “you know the girl sitting next to you is a redhead right?” and I reply “yes, we are… actually… here on a date.” He said “wow, this has never happened to me during this bit before” then cut me some slack and moved on.

In the larger scheme of things, this probably wasn’t that bad, and the date wasn’t going spectacularly anyway so it wasn’t like a huge loss, but it definitely made things very awkward for the rest of the evening. It was kind of a relief when she said no to a second date because then I immediately texted her back and was like “That’s fine OH MY GOD CAN WE TALK ABOUT HOW CRAZY AWKWARD THAT WAS?” and she was like “I KNOW!!”

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