Most Cringeworthy Dating Stories

The world of dating is notoriously difficult at times, and we’ve all experienced some awkward, funny, or downright weird dates. The lovely Reddit users share their most cringeworthy dating stories for the world to laugh at and commiserate with.

“He told me I looked different than what he expected, and offered me gas money to leave.”

Getting a Little Too Spicy!

Well years ago like 35 years ago, this guy kept asking me out so finally I decided I’d go to dinner with him. I told him 1 dinner only nothing more nothing less he said ok. We went to a really nice restaurant. There was a bottle of hot hot peppers on the table and he decided to impress me by eating the bottle of peppers. I told him not to do it but he did (he ended up with a mouthful of these hot peppers) and he ended up on the floor in pain. The servers rushed over to help him. I had no idea what to do and frankly I was po’d cause I told him not to do it. He lands in the hospital and I never saw him again. Luckily I’d taken my own car. I might seem cold hearted but I told him about 10 times not to do it.



Love From a Distance

I went to see avengers infinity war with this lovely dude, we didn’t prebook tickets thinking it wouldn’t be too busy.

It was packed and we could only get separate seats.

So uh, we still watched the film, just at opposite ends of the cinema.


Toot, Toot!

I had a man leave the table, walk a lap around the restaurant and return to his seat. I asked where he went, and he said he had to pass gas and didn’t want to do it at the table, so he let it go as he walked around. Yeah, that was our first and last date.


How Many Red Flags?

Most recent one was an unemployed waiter who was really psyched about the fact that he’d quit his most recent job. Told me nonstop stories about himself and his future in serving and how job offers were just pouring in, but he was being choosy. Oh and his last girlfriend was killed in a hit-and-run, AND he is emotionally abusive (no joke, admitted it using those words).


May day, May day!

I was invited back to hers to “watch plane crash videos”


Probably Won’t Lead Anywhere

A very long time ago I went on a okayCupid date with a Muslim doctor. At the very beginning of the date he said, “I can only marry a Muslim woman but I will have sex with you” after that I got out of there as fast as a could but he still asked if he could hug me goodbye!


Wrong Number!

once i invited a girl i thought of as a friend (she was single) out to a movie along with other friends.

i thought i made it clear that more people were coming-with. this girl usually never wore make-up and never dressed up particularly nice. both her and i arrived early to the theater and she was glowing . the whole ten yards on clothes and makeup. this made me think she thought it was a date. at the time i was dating someone so i texted her and said “i invited so&so to a movie with friends and i think she thinks it’s a date”

i accidentally sent this message to the girl i invited.

neither of us said anything about the fact, the rest of the people arrived and it was one of the most awkward nights of my life.


Mr & Mrs Cringeworthy

Went on a date with guy who suggests we meet at a hotel bar. Turns out the hotel is hosting his law school reunion. There’s a table full of name tags and I find mine- it’s my first name with his last name. The explanation being that he “didn’t know my last name.” All of his law school classmates start asking me how long we’ve been married, when did we meet, etc. My response “Tonight.” I say I have to use the bathroom while they’re passing out hors d’oeuvres and run for it. He texts me the next day asking if he’d said something that upset me.


Honesty is Always the Best Policy

I used an online dating service a few years ago, and it matched me with a guy. I talked to him a couple of times on the phone, mainly to see if he sounded serial-killer-ish or weird. He seemed okay, except he kept saying how important honesty was to him. Like a lot.

After a week or so, we agree to meet. When I got to the restaurant, I didn’t see him at all. Finally some guy walked up to me at the bar and introduced himself as my date. I didn’t recognize him because in his bio, he used his younger brother’s pictures – 18 years younger brother’s picture. I told him I had to use the restroom, and walked out. Honesty, my a$$.


It’s a Lovely Game

OK so on my second date with my first “boyfriend” when I was 15, we went to a local cafe. this cafe happened to have a wall of board games to play while waiting for your food. I spotted scrabble, which I love because I have a large vocabulary and I’ve been playing since I was little. He seems kinda put off by it, but I insist we play because I’ll “kick his butt!” He was a smart guy, so I assumed he was just being humble. After I took my first turn, he kept looking at his letters, rearranging them, and acting generally puzzled. I playfully said “what’s takin ya so long, slowpoke?”

He replied “I’m dyslexic.”


Baby Mama

25/M, I was about 22 at the time. Met this girl at her college (I was visiting a few friends), asked her out. A week later, we go out, she doesn’t eat a morsel of the meal she ordered, conversation was… well, stunted (i.e. monosyllabic responses to my questions). I guess she was probably super nervous, especially noticeable by the way she constantly unblinkingly stared at me. Decided to ask her if she’d like to stroll through the mall next door and the first store she drags me into (literally pulls me) is the Children’s Place.

Starts browsing clothing, holds some outfit up and asks me if our kids would look good in something like this in a total matter-of-fact voice. I broke things off after that date, for obvious reasons, but still got weird messages from her for a month afterward.

I’m not sure if this was funny, worst… or some combination of the two.


Searching for John Doe

There was the time my date and I were supposed to meet at a local coffee shop. But it had just closed for renovations. It was blockaded off and I couldn’t even get in the parking lot. So I parked at the shop next door and watched all the cars that tried to turn in.

I didn’t have enough signal to message him in the app to let him know where I was. So instead I walked up to every man I thought sort of looked like him and was like “Hi, are you John? No? Oh sorry, my bad.” The best was the dude who said “No, but if it’s not weird I can pretend I am!” 


So there you have it – these poor Reddit users have shared their most cringeworthy dating stories in all their finest glory.

What’s the funniest or most awkward dating experience you’ve had? Let us know in the comments!

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