17 People Share Their Most Brutally Cringeworthy Hook-Up Story

I recently asked my friends and followers to share their most embarrassing/cringeworthy hookup stories, and they did not disappoint. Some names have been changed, but THE PAIN IS REAL.

1. Jackie

My first boyfriend and I were dating for about a year before we finally had sex, and we decided to do it on the floor of his family’s basement rec room, which was right next to the stairs that led down from the living room. About halfway into our virginity-losing session, his mother pops her head in to ask if I can stay for taco night, and we both scream at her to not come down the stairs. She knew exactly what was going on, and needless to say, taco night was ruined that week.

2. Lily

A dude and I had been talking online for like, way too long. We both knew we were only ever going to hookup; there was no real chemistry, just a moderate physical attraction that was pretty hot at the time but was always doomed to quickly fizzle. So we’ve been talking for almost 3 weeks and FINALLY homeboy invites me over. He does so on a Friday night when I’ve been drinking. Heavily. I’m hammered and have been for a while so yes, I thought jumping in a cab at 2 am to meet this dude for the very first time ever at his place was a great idea. Not my finest moment but we all have lapses in judgement.

I arrive and thankfully he’s just as drunk as I am. We proceed to have the sloppiest, most awkward (but still kind of fun) sex I’ve ever had, before or since. Everyone finishes, we pass out in his bed, and I wake up in the morning with a semi-intact, if blurry, memory of the night before.

While dude is sleeping I stumble to his bathroom to try and salvage last night’s makeup so I can walk of shame myself out of there and much to my surprise my face is covered in blood. On my mouth. On my cheeks. On my nose. What the hell? And then it dawns on me. I’ve started my period a day early and we were both too drunk to notice. I’ve started my period a day early and at some point in the night I let this stranger go down on me and then I made out with him and then I slept in his bed with nothing to shield his poor sheets from my perfectly natural but so poorly timed womanhood. And let me tell you something about my period: it does not fuck around. That shit shows up with a vengence and makes no apologies. So I’m in trouble.

After I clean myself up I creep back in to the bedroom to assess the damage. Sure enough, it’s everywhere. His hands. His dick. His face. His sheets. Everywhere. But he’s still out cold and this is the first (and most mortifying) time I’ve anonymously hooked up with someone so I panic. I grab my things and I bolt.

I get home. My phone had died in the night so I plug it in. A text comes through from the dude: “I was going to double check that we used protection last night but considering what I woke up to that seems like a moot point, wouldn’t you say?” He was trying to be funny. I haven’t talked to him since.

3. Nicole

Upon going home for winter break a few semesters ago, I realized that I hadn’t really planned for most of my old friends having jobs and actual things to do instead of hanging out with me. One afternoon, I decided to combine the trifecta of foolishness: boredom, horniness, and Facebook. Scrolling through my timeline, I stumbled upon a former high school classmate that I had once hooked up with. I decided to act on my recklessness, and after a brief and thirsty conversation via messenger, he was texting me that he was outside.

I had the entire house to myself, because my mom was working a night shift and my dad wasn’t due back until midnight. Me and my one-nighter had one of those incredibly awkward conversations that only precede pre-arranged sex; I think I asked him how school was going (he wasn’t enrolled). The foreplay was clumsy and since he’s about a half inch shorter than me, limbs and members were getting accidentally bumped and pushed. Fortunately, once we finally got into it, it was glorious.

The only thing I had remembered about this guy was that he was pretty well endowed, but either my memory was modest or those infomercials about growing your dick aren’t lying because homeboy was packing. He was stroking it from just the right angle, and I was beginning to feel the tingling tension signaling a coming orgasm in my toes. I wrapped my legs tighter around him and gripped him in a hug.


I stopped him for a moment. Was that the garage?


FUCK! It was the garage! My dad was home early! “Shit, shit, shit!” I hissed, and threw the guy off me. It’s important to note that at this point, in the deep throes of sex, my pussy had gone into gripping mode (shout out to my daily kegels). My vag hadn’t fully unclamped, so when I unexpectedly pushed him off, this guy squealed. Like a piglet. Jesus H, I thought, is he fucking coming right now? He was. All of this happened in about 5 seconds. In the next 5 seconds, I scooped up his clothes, threw them at him, and started hissing at him to get dressed. I hurriedly tied my robe as I heard the garage door motor stop. I figured I had about 60 seconds to get my booty call down the stairs, through the living room, and out the sliding door to the back patio before my dad walked in and I had to explain this shit. The guy didn’t even have his shirt on yet. I didn’t care.

“Come ON!”

I grabbed his arm and manhandled him down the stairs like a rag-doll. It was at this point that it really hit me he didn’t have on a shirt. It was somewhere around 30 degrees outside since it was around christmas. When I slid open the patio door, he shivered. I pretended not to notice.

“Just go down the deck stairs and through the gate.”

“What about my shirt?”

“I’ll give it back later!”

BBBBBRRRRrrrr. That was the garage going down. That meant I had about 10 seconds, tops.


I shoved him out into the wintry air and he gave me a puppy dog face as I shut the drapes. I turned around and my dad opened the door.

I was breathing so hard at that point, and I didn’t want to give myself away. I mumbled a hello to my dad and ran back upstairs.

In my room, on the floor was one of those gaudy sweatshirts with a gold foil design on the front.

My phone bleeped with a new notification from the booty call:

So that was fun, huh ;)

4. Julie

I’d just broken up with a boyfriend and was feeling in the pits of despair and so I went out with some people who I didn’t even know that well. We went to a house belonging to a guy who I did not know at all. And I was really fucked up on all the substances and ended up inviting him back to my house, where we started messing around and eventually having sex. Then I started thinking about my ex and started crying. While we were having sex. I ended up kicking him out of my apartment without his shirt on and to this day I do not know for sure if I ever got his name.

5. Jack

Ok. I have some pretty bad hookup stories. I’m the bad hookup fucking master. But my best failure involves an IMMEDIATE rejection. Like. The hookup didn’t quite get there. But I do vividly remember being dumb and making “all the right moves.” I had the liquid courage, Eternal Sunshine of the Spotless Mind was playing. To Freshman Me, conditions were perfect. But I talked about my ex-girlfriend for 20 minutes, before exclaiming “We should make out, right?!” I have no idea what turned her off. I’m such a nice boy. Long story short, I ran to the whiz palace and she slid my copy of Eternal Sunshine under the door. That was the day I learned the vital importance of nuance….and….you know… not dumping your “emotional baggage” on virtual strangers.

6. Jacob

The girl I had liked for LITERAL YEARS finally decides to (drunkenly) make out with me at a friend’s pool party. I knew that she didn’t really like me, but I was 19, hammered, and so overwhelmed with the whole thing that I just went for it. I was harder than I’d ever been in my life — this girl looking at me would give me a boner, actually kissing her felt like my dick was going to explode. We ended up going upstairs to my friend’s parents’ room where I fingered her for approximately 3 awkward minutes before she said she was tired and fell asleep on top of me, and I fell asleep eventually with the most painful boner of my life. The next morning we realized we had stained the sheets through to the mattress with our chlorine-and-alcohol soaked bathing suits, and spent the next day at Sears replacing them while she wouldn’t look me in the eye.

7. McKenzie

So my junior year of high school I was dating a guy who liked me significantly less than I liked him. Therefore when March 14th (international steak and a blow-job day) came around, he was persistent that we celebrate. We were in high school at the time so his mom was home and he had a fairly small house — we weren’t going to be able to do anything. So as he was driving me home for the night he requested I give him “road dome.” I was reluctant, as I had never done it before and I didn’t feel very well, but for irrational fear that he’d break up with me if I didn’t do it, I performed oral on him while he was driving. As we got closer to my house he wasn’t finished, so I told him to keep driving a little longer. I live near the ocean, so he drove straight on a road going towards the public beach. He pushed my head down to encourage me to go deeper, as we simultaneously went over a bump on the road. I gagged and then proceeded to puke on his dick. I then opened my door while the car was moving and finished vomiting. He broke up with me 2 weeks later and I won’t give “road dome” to this day.

8. Sarah

I was going down on a guy and he told me I reminded him of his sister……..

9. Ashley

I was freshly-single and (way too) ready to mingle, so I thought I would preemptively cockblock myself by wearing one of my roommate’s shirts. (My shirts, and bras, seemed to disappear at the slightest hint of a hookup, which was a problem because once your top is off, your pants soon follow.) She was a proud member of the Itty Bitty Tittie Committee, and I was proudly not. This shirt took 3 sets of hands to squeeze me into — there was no way it was gonna be coming off easily. Later that night, I found myself in the bedroom of this guy named Rusty. Never has anyone looked more like a guy named Rusty than Rusty. The 3 sets of hands that had helped me earlier where in various other bedrooms in the house making mistakes we would laugh about the next morning.

I make some asinine, albeit true, comment about how one of those girls (my roommate) was a virgin. “Haha, she doesn’t know what she’s missing out on!” I said. Totally, embarrassingly leading him on. (100% not my intention.) So he thought I was about the peen, which I am, of course, just not that night.

We started making out. Then he tried to take my shirt off. Poor guy didn’t have a chance. But oh, did he try. He tried real hard to get that shirt off. At one point he was squatting on the bed behind me using both hands. I was giggling like a damn fool because my evil plan had worked. He gave up on my shirt and grabbed a rubber.

“Hahh, um, nooo. I’m good. I think I hear my friend!” I panicked.

“Wtf!” He accused.

“I’m in my period, dude, sorry.” Another asinine, and totally false, statement.

“I don’t believe you.” I’m sure he could already feel his balls going blue.

I asked him if he wanted to see my tampon string.

He declined.

I ended up sleeping the too-tight shirt, alone, in my own bed, that night.

Preemptive cockblocking FTW.

Sorry, Rusty.

10. Shae

This guy I went to high school with and always had a thing for (we both always had our own gf/bf) came up to visit me during my birthday weekend my freshman year in college. 3 day weekend. 1st night we successfully made out at a frat but I was extremely drunk & proceeded to puke (very neatly btw) into a solo cup. Night 2: we went to a house party and he was in the basement grinding with a rando all night. Night 3 rolls around and I finally get this idiot into my room. He keeps having to go to the bathroom and eventually just ends up puking in my trash on my dorm floor. I woke up the next morning and he had slept in my roommates bed. Cool!!

11. Mark

Last August I accompanied a college basketball team to Cabo San Lucas. First five days of the trip were game days, but the remainder of the trip was dedicated to partying. On the last night of our trip my buddies and I hit the infamous Squid Roe club for the fifth night in a row. I started dancing with this young lady, a couple things lead to another and she wants me to leave with her.

She doesn’t want to walk to my hotel, but she doesn’t have her room key.


In my drunken brilliance I declare we should hang out on one of the lounging beach chairs. It’s 3 am and the place is desolate.

We do the deed, I finish too quickly and in my guilt-ridden refractory period I offer to eat her out, to which she complies.

I’m nomming my heart out of her fantastic vagina when I hear, “excuse me, sir”


Local muscle had crept up behind me with my ass in the air and pants around my waist and told me and my similarly naked ladyfriend to GTFO, seeing as I wasn’t a resident of that hotel. Or something.

12. Seth

She shit on me during anal. I wish this were more interesting. (To be fair, it wasn’t a full-on shit, but it was like, not NOT a shit. She just sort of like, emitted poop onto my dick.)

13. Sara

Freshman year of college I went over to this guys place that I had met the night before. Mind you this was a freshman dorm. It was the middle of September and I was in a crop top and a mini skirt. He brings me upstairs and we start talking, and he mentions that he’s a virgin, and I let it be known that we will not be having sex. So we sit on his twin bed (it was a double…so his roommates bed was about 2 feet away) and he tells me about his interests and we watch Superbad. The window was open, and there was a warm draft coming in but he suddenly mentions that he’s freezing and gets under the blankets. I get where this is going, and next he asks if it’s okay if he takes his pants off. He lays down and I straddle him while giving him a dry handy, we begin to make out and he doesn’t go for anything below the belt on me. About 10-15 minutes into it he’s laying back with his eyes closed, hands behind his head (like when you do a sit up), and starts breathing in a way that can only be learned in a Lamaze class. A few more minutes go by…and he never opens his eyes…so I start getting tired and turn my head to see Billy Blanks’ Tae Bo workout playing on the TV. I begin mimicking the rhythm of Billy’s motions with my hand job and realize how ridiculous this is. This goes on for at least another 20 minutes and finally about an hour into this really weird hand job we hear his door handle begin to shake. He shoots up and yells STOP while I slink back on my shirt and start laughing hysterically, in walks his soaking wet roommate (one of those rainy, humid nights) who happens to be a casual acquaintance of my friends who I met for the first time that night; and still a friend of mine to this day. I say hi to his roommate while laughing, and this guy just looks mortified. He walks me downstairs to leave me with the most awkward side hug, and then I remembered sometime during that hand job he asked if we could have sex next time and if I liked doggy style. I avoided him like the plague, and he tried to get in touch with me over Thanksgiving break but I had just finally worked out my other arm to be of equal strength after that tae bo hour long session.

14. Callie

A few years ago, I was at a friend’s bachelorette party at this terrible bro bar where we were all hanging out being WOO girls and having a grand old idiot time. A bachelor party showed up shortly after we did and we ended up kind of hanging with them for most of the night. One of the dudes and I kind of hit it off, which led to us making out on the sidewalk at 4 am, which led to me inviting him back to my apartment for some sex. This was literally the second time in my life I’d done something like this. We got to my house and my cat was FRANTIC, running back and forth and yowling like crazy. I shut her out of the bedroom but she was determined to just run around and yowl. Finally, I let her in, thinking that would calm her down. It did not. Meanwhile this guy’s boner is like :(, so finally I figure out that she’s upset because there is a pigeon roosting right outside my window and she really really really wants to kill it. The hookup continued anyway. The end.

15. Beth

A long term boyfriend and I were having sex and I was on top, and it was dark. And I moved my hand at the same time he was moving his head in this moment of horrible coalescence that led to my thumbnail catching the skin about a millimeter from the outer corner of his eye and scratching downward. We stopped. His facial wound made him look like a Thundercat.

This was a week before Christmas and so we had to make up a lie about how he got it to tell my family.

16. Dave

I got sucked into a molly-induced game of truth or dare at the age of 27, and somehow ended up letting a guy finger my ass for about 10 seconds because I thought that it would lead to me having sex with the girl I was really into who was also playing the game. (She was the one who dared me to do it, because she said she would think it was “so sexy.”) We never actually hooked up, and she got sober a few months later and basically cut us all out of her life because she was “putting the past in the past.” My anus will never forgive me.

17. Thea

This isn’t so much cringeworthy as it is just plain horrible, but it’s my biggest regret so I must (anonymously) share. I had been secretly in love with for my boss for years, and always suspected that he was, too. We would flirt and flatter each other while drunk at company parties, and hint around our feelings, but it never went anywhere because he was with this girl I couldn’t stand (of course). One day, while REALLY drunk at a rooftop party, we start making out — in FULL VIEW of the other employees who were still at the party, too. They didn’t say anything at the time, but I knew things would never be the same with them again. (Drunk me didn’t care, though, she was just too happy to think about it.) We ended up getting a hotel on the way back (a Sofitel, because I am a classy floozy) and had incredible sex until literally six in the morning. But as soon as we dressed and left, it was like someone had turned off a light switch. He barely spoke to me, and the other employees who had seen us were icy in the office. When I tried to bring it up once a few weeks later to him, he all but pretended not to know what I was talking about. My heart was totally broken, and I began to realize that he didn’t have unrequited love, he just wanted to fuck me. I left the company shortly thereafter, and recently heard that he and his girlfriend at the time are getting married. I have honestly considered burning down that office building.

Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.

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