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

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!!”

rawlingstones Thought Catalog Logo Mark


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