A Bunch Of 20-Somethings Describe Their Weirdest Hookup Moments

In a comical effort to help aid myself (and the general public) of feeling like I am not the ONLY one that (repeatedly) gets myself into such obscene and uncomfortable situations here are ten of my friends on their weirdest hookup moment.

By Ashley Twigg

Updated 11 years ago, March 19, 2014

I am all too aware that my 23 years have been riddled with awkward, ridiculous, and embarrassing moments. So in a comical effort to help aid myself (and the general public) of feeling like I am not the ONLY one that (repeatedly) gets myself into such obscene and uncomfortable situations here are ten of my friends on their weirdest hookup moment.

I was hanging out with a new guy – there was unspoken chemistry but nothing had ever happened. He came over to make me feel better as I was sick, and we ended up making out. Mid-make out, I felt wetness and realized my nose was bleeding. Realizing that my blood was all over his mouth, I ran to the bathroom… but he was more than willing to continue when I returned…awkward.

Oh damn. He just yelled, “Oh damn” the entire time.

I met this guy on Tinder and for our second “date” he wanted to meet at my apartment. What that really meant was come upstairs and make out on my couch. I felt really weird because he didn’t know what to do with his hands and he barely touched my boobs. Which is so strange when you have big boobs. After a while, some dry jumping started happening and I felt this warmth that wasn’t coming from me. He jizzed his pants. Jizzed. His. Pants. After that I told him I had to go have dinner at my mom’s house and just never returned his texts.

When I was 18…. I smuggled my way into a bar on New Years Eve, drank for free because it was my boss’s daughter performing. I ended up making out with my boss’s 30-year-old firefighter-with-children brother…in front of my boss…and his whole family.

He was quiet, just breathing heavy until the hulk came as he did. Then it literally was a “RAAAAWRRRRR!”

Back in college, the night before classes started went to the bar, found this really cute tall guy. Dancing turned into kissing, kissing turned into him coming back to my dorm room. Kid was moaning so loud and I wasn’t even having sex with him. Mind you everyone was in my common room and heard everything. He kept saying you’re so good at what you do, you’re amazing. Just giving him a good ole handy, I got freaked out, wanted him out, he didn’t leave until 5am. Didn’t want to exchange numbers, gave him a fake one. had an 8AM class, he sat next to me. FML.

One guy told me to call him “bad boy” while we were doing it…

We were shattered and on a friends futon in their basement, we rolled over, the mattress closed up on us and the friends mom came down the stairs while we were naked and stuck in the futon.

Freshman year I went to a fraternity party and ended up sleeping with one of the guys. The next morning his roommates were extremely confused as to why I was coming out of his bedroom with his shorts on. Apparently, he is very much gay and had never been with a girl in his life.

One time I was at a bonfire at a kids house. I really like trucks and I saw a super nice Chevy Silverado in the driveway, and said, “Wow that’s a nice truck.” I was unaware that in guy language this meant “I want to suck your dick,” but it does. So he sweet talked me by saying, “Hey you wanna go for a ride in that sweet truck– to McDonald’s?” Now to drunk me this basically seemed like my Prince Charming arriving. So we hop in, he drives about 200 feet around the corner and he stops and shuts the truck off. Then he whips his pants off faster than anyone I’ve ever seen strip down – and at first drunk me thought okay. So I made out with him, did some touching and feeling around. Then I snapped back into it- got pissed I didn’t get a nugget happy meal, yelled at him and walked back to the fire.