Hey Reddit, what’s your most embarrassing or shameful hookup story?
Well, Redditers delivered the answers to this question in the most hilarious, cringe-worthy ways!
From being stuck in a glass box of shame, to getting a discount coupon to Perkins the morning after, to hearing about all the gross things you wouldn’t dare discuss with your friends, here are 55 cringe-worthy hookup stories that you never knew were even possible.
1) Oops, That’s Not A Condom!
All this guy had to do was grab the condom he had in his pocket. Things got spicy, but not the way he had planned.
2) That’s What Good Wingmen Are For
When you’ve had a little bit too much to drink, it’s easy to forget that you have wingmen right by your side. And they can see everything you’re doing!
This is why you shouldn’t lose your virginity in the bathroom at a big party. You never know who’s lining up at the door to listen in.
4) Nope, It Never Happened!
There are just some things moms don’t ever want to discuss with their sons. That time you got caught making out with her cougar friend is one of them.
This shy, teacher’s pet just wanted to hook up with the high school hottie. Instead, she ended up doing the 3am walk of shame.
6) She Puked All Over His Silk Sheets
She got wasted on St. Patrick’s Day and went home with a man-friend. Unfortunately, neither one of them had the luck of the Irish on their side that night.
Sometimes language barriers can get in the way of pursuing a romantic relationship. This woman kept screaming at him in Spanish, and to this day he can’t figure out what she was trying to say.
She couldn’t even get the walk of shame right. She got stuck between two glass doors on her way out of the building!
Congratulations! When your hookup hands you a discount coupon for Perkins restaurant after he urinates on you in the shower, you’ve won the award for worst hookup ever.
10) Hide-And-Seek With Her Dad
She tried to hide her naked bits from her dad after getting caught with her boyfriend. Can’t blame him for never bringing it up at the dinner table.
11) Shhh, My Mom’s Alseep
We’ve all heard this story before – strangers get drunk, they go back to her hotel room, and do the dirty deed. But, what’s different about this hookup tale is the surprise ending!
12) Awww, There’s A Good Baby
This drunk virgin hopped into bed with a cute sorority girl. He thought he had ecome a man the next morning, but it turns out he was still just a baby.
13) Coming Out Of The Closet
This couple got hot and heavy in the coat closet at a party. It was great, until she started crying about her parent’s divorce and he couldn’t wait to come out of the closet!
14) It’s A Money Belt, Eh
This Canadian girl hooked up with Australian dude in Belgium after a day of sightseeing. But, after the clothes started flying off, she realized she forgot to remove her hidden fashion accessory.
15) He Told Off His Roommate
This guy came home drunk with a girl he had been crushing on for years. His “roommate” wasn’t very appreciative, though. Wait for the hook at the very end of this cheeky story!
After morning after regret sets in, you just want to make an exit as quickly and as silently as possible. Unfortunately for this girl, the ceiling fan had other ideas.
This woman got hot and heavy with her boss at the office Christmas party. She didn’t get a raise, but he sure did!
When a guy in the viking hat burst into your room and asks if you’re finished, you know you’ve hit rock bottom. It was her first, and last, walk of shame!
Things were going great and this guy was feeling lucky! Too bad he turned out to be a bleeder on his very first try.
His play date demanded to hear him call her name. He knew it rhymed with fajita. Was it Pita? Maria?
21) That Wasn’t The Bathroom
We all know that guys urinate in strange places when they’re drunk. They think it’s the bathroom, but it’s not.
This is the real walk of shame. This guy couldn’t help himself and got together with his friend’s wife. Soon after, the couple divorced, and he just can’t forgive himself.
This is why I put my mattress directly onto the floor. There’s no room for creeps to hide out underneath your bed.
The first time is different for everyone. But this guy’s first time without a jimmie hat made him a one-hit wonder with the girl he was with.
This cute Mormon got drunk after having a fight with his lady, and was a born again virgin until that night. WAS being the operative word. Awkward!
26) Tinkle, Tinkle, Little Star
Little kids wet their beds all the time, but it’s okay because they’re kids. When you’re a grown-up, women kind of frown on that sort of stuff.
27) Awkward Morning After Request
His gay friend brought home a girl for him. Things didn’t go well, and he found himself having to make an awkward request the next morning.
28) His Girlfriend Was Right There
She made out with a guy who stopped mid-way and said that he had a girlfriend. Turns out the girlfriend was a the same party they were at.
He made out with a girl, and that was all fine and dandy. It wasn’t until a month later that he found out she was the niece of a family friend – and she was underage!
She said she wanted a puppy. He thought she said something that rhymes with puppy-me.
31) Back In The Saddle Again
This is what happens when you get so drunk that your eyes start to deceive you. When the two of them work up in bed the next morning, they realized they were each other’s ex!
The first day of college can be a scary experience when you don’t know anyone. Well, this guy met someone, but his “welcome to college” moment didn’t turn out like he had expected.
I guess the moral of the story is not to have seizures when you’re hooking up, but it’s not like she could help it. Calling the cops on her was probably not a good idea.
He thought he was pulling out at the right moment, but he miscalculated. His girlfriend thought it was funny though!
35) “I’m still up for it if you are.”
If we’ve learned anything from everyone’s awkward hookup experiences, it’s that getting drunk often results in things coming up when you least expect them to. But, that’s okay as long as you’re “still up for it” after all is said and done.
36) He Tried To Hook Up With A Lesbian
Sometimes when a guy is lonely he looks to online dating for some fun. But, he should have known better than to go out with a lesbian.
37) Weird Face, No Sounds
Some people are screamers, others are moaners. But this girl was making a weird face and didn’t utter a single sound.
He made out with a coworker at a going away party. But when she started crying mid-way into their heated moment, he was the one who wanted to get away.
39) Hush Little Baby, Don’t You Cry
When her fiance dumped her, she started medicating herself with random hookups. She tried to warn them about her weird “sex crying” but they didn’t seem to get it and tried to shush her.
40) She Couldn’t Hold It In
Have you ever had the urge to go pee in the middle of having sex? Yeah, it’s probably not a good idea to actually go through with it.
This is the kind of thing you would imagine happening to a guy when he was all by his lonesome. But, he accidentally hit a bullseye because his girl had an unknown aversion to him!
42) Trashy Cinderella Story
This trashy Cinderella story was cut short when she ran away from the ball and left her weave under Prince Charming’s Couch. She thought the unhappily ever after fairy tale was over, but it was’t.
43) Yeah, That’ll Be A No From Me
Have you ever been out with someone and had a really good time, only to discover that you totally misread the situation? Kinda sucks when you don’t discover that until the morning after.
44) He Probably Rolled Over In His Grave
It was a sweet story. Until he found out the girl he hooked up with was just having rebound sex.
45) Ewww, His Sister Was Right There
This guy started making out with his sister’s friend after getting drunk at her graduation party. He thought his sibling had passed out on the floor along with everyone else, until he suddenly heard her tell him to stop fiddling her friend.
This guy had everything going for him. He was vegan, had a glass eye, and smelled like sausages. Yep, she can check that glorious hookup off her bucket list!
Those four little words are hookup suicide. Needless to say, it totally killed the mood – and also the poor guy’s ego.
48) Two Mattress Dances In The Same Day!
This woman was on vacation in Switzerland. After doing a morning mattress dance with one guy, she decided to round out her European experience by doing another mattress dance in the evening with an entirely different dude.
49) He Was Really Into That Lamp
He was drunk and having a loud conversation with a nearby lamp. She quite possibly prevented the most embarrassing hookup ever from happening that night!
50) Hooked Up With Her Friend’s Crush
The hookup part was totally fine. It’s what happened afterwards that made this college Freshman feel really bad.
51) That Babysitter Was The First Clue
When your date takes you home and you see her pay a teenage girl some cash, that’s your first clue that someone else is probably living at her home. He shouldn’t have been so surprised when a 9-year-old woke him up asking for breakfast the next morning!
52) What’s Your Name Again?
In a strange twist, this guy hated himself for not remembering his hookup’s name. So he stopped cold turkey and made her go home before they even finished.
53) He Broke It Off – Literally
This guy was getting hot and heavy with his girlfriend and he grabbed the headboard for some support. But it got so heated, the headboard came off in his hand and the bed collapsed!
She was a sweet girl who was doing a nice thing for him in the back of the school bus. Too bad she died and he felt really guilty about it.
55) Bloody Nose, Who Cares?
This girl got her nose pierced, but it accidentally came off during their sordid hookup. Even though she was bleeding all over him, it didn’t stop them from continuing on with their love affair.
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Hey Reddit, what’s your most embarrassing or shameful hookup story?
Well, Redditers delivered the answers to this question in the most hilarious, cringe-worthy ways!
From being stuck in a glass box of shame, to getting a discount coupon to Perkins the morning after, to hearing about all the gross things you wouldn’t dare discuss with your friends, here are 55 cringe-worthy hookup stories that you never knew were even possible.
