UConn students were asked to reveal their most embarrassing and funny hook up stories for this year’s edition of UConn’s Most Embarrassing Hook Ups. All responses are completely anonymous and hilarious- so get ready to laugh.
Note: NSFW. Responses may have have been edited for obscenity and/or clarity.
* * * * * * * * * * * * * * * *
“Stayed at the apartment of a guy from my hometown who was 2 years older… Made him bring me home at 6am for my “8am” (I really just had to poop).”
“So one time I was hanging out with a girl and she wanted to show me her new speaker which required her to turn off the light (I still don’t know why) and she used my phone to put a random song on which happened to be “Cheerleader” but it turns out I had just searched “Cheerleader” so we had sex while 20 different remixes of OMI’s “Cheerleader” played, on repeat, even while I slept over. Needless to say, even though the sex was great I have probably heard that song enough for two lifetimes.”
“I was really into this guy I met and we had already had sex a couple times before. I didn’t totally love the sex, so I strived to make it better, telling him I liked it rougher. Needless to say, the kid definitely upped his game and it felt pretty good, and we were in missionary position when I heard a pop. He broke my F*#%KING collarbone! Not only that but somehow he managed to bruise my neck like I was choked to death. Don’t think for a second I didn’t invent a very good story to tell my mom as to why I got hurt like this. And then, we still powered through, continuing to have sex with a broken collar bone in the following weeks.”
“The other day I got my period right in the middle of you-know-what with this cute guy I had been talking to. And of course it wasn’t just a little blood… It looked like it was something out of a Criminal Minds episode.”
“We met at the bar and he came back to my place. We were pretty drunk I’m not gonna lie, but never have I ever had someone pass out while going down on me. I never want another man snoring into my vagina ever again.”
“Ok so I had just gotten out of a two year relationship when I decided to hook up with this guy. I had met him once before we hooked up so I knew he was really cool- we will call him Tom. Tom and I went into my room and we were making out. We did some touching but we didn’t have sex. I actually had a super good time with him talking and hanging out and cuddling. We were telling each other weird stories about sex stuff and laughing really hard. He told me about a year ago he was watching a girl and a guy make out at a party, and they came up and asked him to join them in bed for a threesome. He said it was the weirdest thing he’s ever been asked but he was like “f*ck it” and went back to her room with them. I thought it was cool that he was so adventurous. I was thinking an actual relationship could come out of this because I was having such a good time with him and we had a lot in common like our majors, and sports and movies we liked. Then I knew he was going to leave soon so we started making out really, really intensely and we were basically about to have sex. I thought it would be hot if I went on top so I like turned him over and threw him down a little and took off my shirt. All of a sudden he looked at me horrified. I was like “What’s wrong?” and was looking up at the wall so I also looked at the wall. Hanging right there straight in his face was a bunch of pictures of me and my ex that I hadn’t taken down yet and totally forgot about. I apologized and said we broke up a while ago. But more horror was still to come. He looked at me and said “remember that story I told you about the guy and the girl? How I went back with them and had a threesome?” and I said “yeah….” and he said “that was the other guy.” My face was bright red and I was like “NO WAY.” Turns out this threesome happened while I was still in a relationship with my ex. So basically my ex cheated on me in a threesome and then I hooked up with the other guy from that threesome. No regrets. Tom’s a really nice guy. Would do it again.”
“Met a guy online – turns out he lives a building up from me in North. Go over to “hang out,” but turns out he’s a virgin and is also diabetic which would have been OK if I had known before almost ripping some wires from his stomach. Still gave a BJ. Just super awkward.”
“I met this hot guy at Huskies on Halloween and we were both wearing nerdy glasses and hit it off immediately. I went back to his dorm and we had a great time (ya know what I mean)… five times in a row. We agreed to continue this for the semester. The following week I came back to his dorm and this time he was alright. During sex, I started touching myself cause I needed to get off somehow, and we both climaxed at the same time. After that, we just lay down. Then he asked me, “How do girls climax? Does stuff come out cause that didn’t happen to you like it does to me.” I just looked at him and said , “Are you kidding me?” So needless to say, I didn’t hook up with him anymore after that. I should have taught him a thing or two to make his future girl happy but I was just too bothered by his lack of knowledge about the female body, lol.”
“The night before break last semester, I accidentally initiated a hookup with a somewhat decent guy in my discussion of like eight people…I had a House marathon with my friends earlier that week and had told him he should join (my fault for not realizing that I mistakenly asked for Netflix and Chill because I’m an idiot and I really do enjoy House). Like always, I texted my best friend who only told me to take advantage of the free suite. He showed up high and acted all paranoid. We started hooking up, but it was weird so I started saying to get him to leave. He stayed until 5 a.m.”
“After a while of debating, I decided to create a Tinder account to see what happened. It came with a good stroke of success, as I managed to hookup with a few girls, (not too many but a handful) over the course of the year. I didn’t really look too far into who knew who though and eventually the girls started realizing they knew the other girls I’ve hooked up with and started fighting each other about it… and that’s the story of how I nearly imploded an entire sorority’s pledge class.”
“I was making out with this guy, and he said he wanted to go further. I was down for that so I said sure. The next 20 minutes were spent with him trying desperately to put his mostly flaccid dick into me while swearing he was hard. Worst hookup of my life.”
“So 10 o’clock rolled around on a Saturday night. My roommates were having a lame party with ugly guys and me and my wing woman had to escape. We decided to grace Ted’s with our presence. As soon as I walked in I was on a mission. As we went to go get drinks at the bar, I spotted an Italian Stallion. I thought to myself, how can I talk to him? Randomly this other guy chatted it up with me and wing woman. He wanted us to meet his other friends and guess who I was introduced to? The Italian Stallion I was eyeing the whole night. It didn’t take much talking so he came back with me and my wing woman. I came back to find my roommates completely blacked out, and I showed him off like he was a new pair of shoes. Just as we take a shot of Fireball to toast to our sex that was about to happen, my roommate who was blacked out came into my room without a shirt on… but he took it like a champ when he was interrogated by her. So fast forward to me on top of him, it was amazing. After, I told him I would be right back and took my naked/drunk self into my roommate’s bedroom. We chat for a little and she finally convinced me to go back and cuddle with the guy even though I just wanted him to leave. Well I came back to my room confused because I didn’t leave my door wide open. My Italian Stallion had taken off and rode into the UConn wilderness. I was so shocked yet slightly relieved.”
“One time I was hooking up with a frat boy who was unable to have sex with me. He then proceeded to ejaculate on my floor and my sorority sister stepped in it.”
“The first time I’ve ever had sex sober, it was with this girl from my math class. I put on a condom, stuck it in and climaxed in two thrusts. I didn’t know what to do so I kept going for another three minutes and then stopped. Most awkward thing ever… ever.”
“Met a guy off Tinder last semester and he came over and we hooked up. We unmatched from Tinder- I swiped left every time he popped up again because he had my number and never texted me again. This semester he finds me on OkCupid and messaged me. I’m starting to think he doesn’t remember me until he starts mentioning things that I told him the last time we talked. He asked to hangout one day when I was in the Union and I said sure. We sat there uncomfortably for 45 minutes pretending like we never met each other while I waited for my next class. It was a great day.”
“Having nothing better to do we decided to go to a Beta bar night, when two frat guys decided to grace my roommate and I with their presence. All was well until our drunken selves were taken into a car; looks like these boys had their own agenda. This is where things got real. I was dropped off-campus with my guy and my roommate screaming “Where are you going?!” Everyone thought she was crazy. The car takes her away and I go up to his apartment. Let’s just say worst mistake of my life. In the end I got $25 out of it for Plan B that I didn’t need. So I took his money like the bad bitch I am and used it for alcohol. Being paid for sex isn’t too bad. BUT WAIT!!!! My roommate was not okay. She tried hardcore to ditch this beady eyed boy so much that she left him in her room thinking he would get sex, but instead ran out the door. Circling Hilltop, she got lost and suddenly out of no where the creep finds her. Like a scene in a horror movie he yells at her for not doing what he wants. Needing to rid herself of this fuckboy she told him after she goes to meet some friend she would find him in the Oaks. He fell for her lies. SO let’s just say you’ve been warned about frat boys.”
“Sex in the cemetery under the super moon. She was a nympho.”
“It was a Halloween night where I had one too many candies. I went to this awesome party, where I met this intelligent, handsome, hot guy. We were by this big white party tent with tons of people. I was about to leave in less than 10 minutes, when suddenly he grabbed me and started kissing me. With my arms around his neck and my phone in my hand, I felt a sudden slip. That’s right, someone stole my phone right out of my hand while I was hooking up with this hot guy. I started freaking out on him, going crazy that someone just stole my phone right out of my hand. I don’t know which one was worse, the embarrassment of getting my phone stolen from my hand while kissing a guy, or almost showing my crazy side within the first hours of meeting him.”
“I was hooking up with this guy I’d met in class and found at a party. I guess he really got into it, because he accidentally somehow snorted in my face mid-thrust and immediately said “I’m going to regret that happening for the rest of my life.”
“For Halloween last semester, I really went full on with the makeup for my costume which ended up being a “magical fawn.” Well… the night turned out to be not so magical when I ended up smearing all my makeup onto the guys face! He had no idea what had happened until I said, “I’ll be right back” and brought a face wipe to remove it all. Not sure if it was awkward for him but it was definitely embarrassing for me!”
“I was at Final Pour, and I was talking this very attractive girl. She said she was leaving and asked if I wanted to go back to her place. Well duh, obviously I wanted to go back. As her friend drove us back to her room, I thought “This is great. Great girl. Great night.” But as we pulled up her to apartment, I got sick. Not like the nervous sick, but like the “I’m going to puke because I’m hammered sick.” We get inside her apartment, and I just can’t hold it in anymore. I threw up all over her carpet, got up, left, and never saw her again. Best/worst part is, I never got her name. Four dollar pitchers from Final Pour can be deadly.”
“One of my friends brought me to a party at some random house down past Price Chopper and it was actually pretty popping. It’s a pretty typical party, and around 11 p.m. (who knows what time it really was) I met this girl who I found attractive and I could tell she was feeling me too. So we talk and dance for about an hour and eventually I ask her if she wants to go back to my room and she says yes. It was a long ass walk back to towers and along the way we stopped a couple times, the second time being at Mirror Lake. We sat down on the grass and apparently lakes at night are a turn on because she started making out with me aggressively. One thing led to the next and we ended up having sex right next to the lake. People were walking by on the sidewalk and could definitely see us, but at this point it was like 3 a.m. and neither of us really cared. After we parted ways and the next morning, I realized I had no idea what her name was or anything about her really other than that she had D cups and she left a couple of mean hickeys on my neck. I’d say it was a successful night.”
“I went on a date with this guy not realizing how completely desperate I looked despite the fact that I really just wanted to get to know him. Looking back walking drunk, in the rain, all the way to the other side of campus looked pretty desperate. However, that’s besides the point. We started by playing FIFA and I won. I was so excited having never played before (my friends later told me he definitely let me win). He offered me tequila and being naive I thought that was so sweet. We were having great conversation until he started furiously making out with me. I wasn’t completely against it at the time, but then he started dry humping me… really hard to the point where it hurt and I wasn’t even reciprocating. I told him I had to leave and he flips his futon into a bed! I again told him I had to go because I was meeting a friend. He told me that I was a big girl and I could make my own decisions and I told him this was my decision. Then he started begging me to stay the night saying we could just watch TV and I could sleep in his roommate’s bed and we didn’t have to do anything. But I had had enough and this was just weird.”
“Buckle up, grab a drink and get comfy folks, because I am about to tell you the story of how I almost lost my virginity during the most what-the-fuck hookup I’ve ever had. It was a chilly October night and my friends and I were headed to a rave-themed party. It was cold, so I had opted to wear an actual shirt; my friends’ nipples were nearly slicing through their neon sports bras, but I was slightly warmer in my spandex and cut-up tee. So there we were, comfortably drunk but nowhere near smashed, waiting for our driver, looking like EDM threw up on us. When we got there, we went downstairs and were immediately hit in the face by a wall of drunk. For anyone who hasn’t been to a frat party, I swear you can get hammered just by breathing the air in the cellar. But hey, that was the goal, and I was having a good time with my girls despite the moist atmosphere (I’m sorry). Then, as often happens at parties, we got separated sometime during our journey to the woods to break the seal. I’ve never been the type to panic when I’m alone, so I just figured I’d make some new friends until my real friends found me. Now, this IS a hookup story, I promise: enter Tall Energetic D-bag, TED for short. I don’t remember his real name. “Ted” and I hit it off really well, and he had an entire bottle of vodka in his hand. He looked like a great decision. Little did I know he was a nightmare dressed like a daydream (again, my apologies.). Flash-forward to the two of us in the now almost empty basement, still grinding away. A guy I went to high school with was standing nearby, watching us with wide eyes—I guess he never imagined little old me could be such a freak. I was now about a 14/10 on the drunk scale, thanks to Ted’s bottle. I turned around to make out with him, and this is where my tale takes a turn for the tragic. He stopped kissing me and asked a question that, in hindsight, should have set off warning signals. “Can I try something a little weird?” he asked. “GO FOR IT BABE,” I hollered over the dulcet tones of “679” playing for the fifth time. Then came what I guess he thought was his power move—before I could even process what happened, Ted had SPIT HIS GUM INTO MY MOUTH. He then shoved his tongue in there with it, bit the gum, and pulled away from me, the string of rubbery mint held between his teeth. Drunk me went along with it, for reasons I still can’t figure out. I should have been horrified. But instead of running for Horsebarn Hill, I decided to say, “That’s hot.” Then came the classic “Wanna get out of here?” and my dumbass reply of “Hell yeah!” We grabbed an Uber and went back to my room, where we continued making out. I was feeling under his shirt, and even now, I’ve got to give Ted some credit, because he had great physique. So what did I do? I took off his shirt, looked at his abs, and promptly vomited. Yup. The Ciroc caught up with me and I barely made it to the trashcan. And what did Ted have to say in response? “It’s okay, just chew some gum, we can still do this.” (What was it with this guy and gum??? Was I going to be tied up with Trident Layers next??) But I went along with it and chewed some Juicy Fruit, then we picked up where we left off. Gross. Flash-forward again: after giving me the worst head I’ve ever gotten, he whipped it out. Now, a more experienced woman’s mouth may have watered at the sight before me, but my virgin eyes widened in legitimate fear. I felt like I was having a staring contest with an elephant trunk. Twice he tried to convince me to bone him, even though I had told him I was a virgin and didn’t want to—and even if I did, there was no way it would have fit. Like, good for Ted, but I’m not Elastigirl from The Incredibles and I really didn’t feel like experiencing death by fratboy dick. So we both just fell asleep. Yup, he stayed over. Morning came (I never did…), bringing with it a monster hangover for yours truly and truckloads of bitter regret. My eyes were almost stuck shut because of the previous night’s mascara and I had a friend due to visit from home in half an hour. “Good morning,” I heard next to me. Oh right, there was also a giant, naked frat dude with a bubblegum kink still in my bed. To reiterate, we did not have sex. My virginity is still very much intact (if there’s one thing from that night I’m proud of, it’s that). …My dignity, however, did not escape unscathed. Ted eventually left, and I had to face what I’d been dreading since I woke up—the mirror. Oh, the horror. The shame. Mascara bits, or as I like to call them, failure flakes, were cascading down my face like the tears my mother would shed if she ever heard this story. My hair looked like a beaver dam, and I couldn’t tell if I’d been given hickeys or if the Kraken had caressed my neck with multiple tentacles. I saw my friend in the dining hall later that morning. After fetching me some much-needed coffee, he looked me up and down and asked, “Rough night?” Buddy, you have no idea.”
Check out last year’s article here.