You want cringe? Oh, we’ve got cringe. First date cringe, in fact. That’s right. First dates. Rife with cringe possibility. So much so, that when Redditor u/noni9191 asked, “What’s the most cringe first date you’ve had?” there were well over a thousand replies. And to be honest, most of them make me wanna ask, “Dudes. What is wrong with y’all?” But I digress. Here are 21 super cringey first date stories that will have you vicariously trying to crawl into a hole that swallows you into another dimension.
1. The Werewolf Family That Howls Together…
u/FallOuchBoy | via Reddit
via Tenor
2. Yeah, Imma Vibrate On Outta Here
u/karamask
Started with a pretty smooth coffee date. Transitioned to a walk in a park, where he sat me down, and started to kiss me. While kissing me he forcefully grabbed my face with both hands, and began humming (whilst still kissing). He hummed louder and louder and then whispered, “I’m polyamarous. Let’s sync our vibrations.”
Done.
u/karamask | via Reddit
3. Steal Your Heart? Nah. That Tip Tho!
u/LostOceanGirl
He asked me out for Chinese food. I had only brought $20 as an emergency backup on advice from my mom. Check came, suddenly he “forgot his wallet”. I had just enough to cover both meals plus tip. As we left, he says, hang on a second and goes back to the table like he forgot something. Then he asks if we can stop by a store as he pulls out his wallet to put money in. He stole the tip.
u/LostOceanGirl | via Reddit
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4. Chaperones Gonna Chaperone
u/Einmanabanana
His cousin (the one who arranged the blind date) stayed with us the entire dinner.
u/Einmanabanana | via Reddit
via Tenor
5. Well, Paul? In What World? Hmm?
u/[deleted]
Went on a date to the zoo with an acquaintance I knew from school. He proceeded to loudly point out all the animals he could take in a fight. In what world could your 12 stone ass beat a fully grown adult gorilla or rhino, Paul? He also said that if he was on a plane and the pilot died mid-flight, he would be able to take over and fly the plane for the rest of the journey. And no, he was not a pilot.
We had lunch in the park and he kept pointing out how I’m prettier than his ex, I’ve got a better body than his ex, I’m funnier and smarter than his ex. Shut the fuck up about your ex and don’t you dare try to lift me up by putting another woman down.
Three days later he and his ex got back together.
u/[deleted] | via Reddit
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6. Angry And Lazy. Great.
u/AbbeyRoad1977
He was wearing a suit and brought a briefcase to a dive bar. Said vegetarians (like me) were destroying the environment. Got angry when I beat him at ping pong. Also mentioned he had some “skin condition” that made it so he couldn’t do dishes so I would need to do all of them, but luckily we could just turn it into a sexy dom/sub game. 🙄🙄🙄 What a weirdo.
u/AbbeyRoad1977 | via Reddit
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7. So Much Stealing
u/[deleted]
Immediately after meeting, he tried to offer me ten bucks for the jacket I was wearing (in December). When I said no, he decided that instead of coffee, we should go thrift shopping so he could find a jacket like mine. Okay…
He then shoplifted from the thrift store, stole my stamp card when I actually bought something, and then asked me to go home and have sex with him. I made an excuse about doing laundry and noped right out of there.
u/[deleted] | via Reddit
@beastieboys | via Giphy
8. Please, No.
u/littlemisslol
“Hey do you want to hear my Rick and Morty impressions?”
Proceeds to scream out quotes in the middle of a croweded restaurant
u/littlemisslol | via Reddit
@therookstarz | via Giphy
9. All Awkward, All The Time!
u/thwoorrpthereitis
Probably the one where the guy tried to get me to play improv comedy games with him and I went on a weirdly long tangent about how I think rabies is cool.
The other one would be the guy who would not stop talking about my old cosplay pics he saw on my Facebook and then went in for a kiss goodbye, I dodged, it landed INSIDE my ear and then we started walking in the same direction to our cars.
u/thwoorrpthereitis | via Reddit
via Tenor
10. *Insert Enormous Eye Roll Here
u/[deleted]
This buff guy with a six pack kept, all night finding any stupid excuse to lift up his shirt and show me his abs. Like he would go to “stretch” and his pinky would “accidentally” pull up is tshirt revealing his abs. After getting NO compliments from me after doing this over and over, I wasn’t going to feed his ego, he actually just pulled up his shirt and said “do you think I have fat on my abs?” And begged me to feel. So cringey. Didn’t go out with him again.
u/[deleted] | via Reddit
via Tenor
11. He’s Never Heard Of A Second Date Either
u/AnnieIWillKnow
He asked me my top 10 favourite films, and then told me how many of them were “right” so he could rate them (and therefore me) out of 10. His metric for “right” was whether he thought it was a good film. For more context, his favourite film was The Dark Knight, and I got no points for The Silence of the Lambs and One Flew Over the Cuckoo’s Nest because he’d “never heard of them so I doubt they’re that impressive”.
u/AnnieIWillKnow | via Reddit
12. The Edit Is The Icing
u/bluetreehugger
It was kind of a blind date I knew of him but hadn’t actually talked with him.
We meet up. He doesn’t have car insurance (this is in a weed legal state and I have pot and edibles and was like uhm no. I will drive. And be sober. But here – here’s a cookie)
We get to the restaurant- he forgot his wallet in his truck. I said I would pay and just to eat something. He said no. And got water. I ordered mine to go and we left and had the longest 30 min drive back to town ever.
If someone offers to watch you eat pancakes – leave.
Edit: he threw up the edible.
u/bluetreehugger | via Reddit
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13. Bawitda-No
u/[deleted]
One time on my sister & her husband brought someone to Thanksgiving for me as a bit of a set up. We were supposed to get to know each other then go out again after that. It was going alright then he said “Kid Rock is a poet.” I have never become so unattracted to someone so suddenly.
u/[deleted] | via Reddit
@thedungeonrun | via Giphy
14. Neigh, I Say
u/damnpixie
This dude invited me to a horseback riding lesson and said we’d take turns riding. Sounded fun! Nope, it was his weekly horseback lesson and I just watched the whole time.
u/damnpixie | via Reddit
@Bounce_TV | via Giphy
15. You Could Say He… Struck Out (I’m So Sorry)
u/lesb1real
He was a friend of my friend’s boyfriend at the time and we went bowling on a double date. No matter what he bowled he’d go to the computer and change it to a strike. After the date, he texted me that he had a thing for making girls gained weight and asked if I’d be willing to indulge him.
Shockingly, he didn’t get a second date.
u/lesb1real | via Reddit
via Tenor
via Tenor
16. That Was Probably The Best Outcome
u/pWaveShadowZone
We went to a minor league hockey game and the game ended while I was in the bathroom and then he and his brother left without me.
u/pWaveShadowZone | via Reddit
@primevideo | via Giphy
17. Are You A Ledge? Because I’d Like You To Drop Me Off. At Home. Now. Eww.
u/Suziepaloozy
He was good looking, tall, and everything was going fine at first. Then he started talking about previous dates and how this one was going so well and we somehow got on the topic of pick up lines. So he said he once told his barista a pick up line and it went like this he orders his coffee and then he added “hold the whip because I already creamed in my pants”. I made him drop me off at home after that.
u/Suziepaloozy | via Reddit
@brooklynninenine | via Giphy
18. That Is Not A Thing. Please Do That Never Again.
via Tenor
19. And This Surprised No One
u/simplygrace
Thought he was a vampire. Told my friends who we were with that he would show them how a real man kisses a girl. He missed my mouth.
u/simplygrace | via Reddit
20. I Can Magic, Too. Watch As I Disappear!
u/Catpoop123
I had been talking to this guy on Tinder for a few days, so we decide to meet up for coffee. I walk in, and he didn’t look quite as charming or put together as he had his pictures (shocking). I introduce myself, sit down, and he stands up and starts loudly doing magic tricks in this quiet, little coffee shop. The date didn’t get better from there. I think I ended up blocking him after he started to send me really dark, bizarre “album art” that he was creating.
u/Catpoop123 | via Reddit
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21. Oof.
u/uselesswishes
He cried when he dropped me off. Saying he’d miss me and didn’t want to lose me. Then preceded to tell me he loves me. We only knew each other for a week. That was our first date.
u/uselesswishes | via Reddit
What About You?
What’s your super cringiest cringe first date story? Tell us in the comments below!
u/FallOuchBoy
We went to his house (I know) where I met his family. He proceeded to tell me that they were all werewolves and they all (everyone in the family) howled in the livingroom. I stayed mostly for fear i would die if I wasn’t nice. He told me he loved me and then said i should keep my neck covered “for my own safety” because I guess he was also a vampire? I don’t like talking about it because it sounds like a lie but I’m pretty sure it traumatized me I talked to some other girls in my high school about it and they all described similar experiences.