25 People Who Had Seriously Awkward One Night Stands


This girl’s parents came home a couple days early and in the morning I was sleeping with her in her room with a couple alcohol bottles surrounded the bed with an ash tray filled with weed and a couple of roaches in there too. Well anyways, parents came home and went upstairs. Was completely naked with no covers on and they just see my shlong just out in the open. I thought her dad was going to beat my ass. Probably the most awkward thing to ever happen to me.


Basically, a day after going too hard at a certain beach music festival I woke up in a really sandy and glittery pull out couch bed in our condo (that I was sharing with my older brother, an older family friend, and their friends) with a guy I barely knew who happened to look exactly like Mac DeMarco. I was horrified because it all came in flashbacks. This very loud, hallway bathroom of our condo sex encounter of the fourth kind. He drank like half a handle of our liquor and I remember him peeing/throwing up at the same time after us doing the deed and then falling into the bathtub. He also threw up on the floor and on my bag next to the couch. Of course, he woke up and didn’t remember a single thing. I honestly felt so bad for him (and ashamed that I did that in front of my fam) that I took him to Waffle House and hung out with him at the beach.


Woke up at 6am laying in the guy’s pee. Hottest guy I’ve hooked up with to this day. Yet he ruined it by peeing the damn bed.


Back when I lived with my dad, I took home a friend’s sister from the bar. Pretty messed up, don’t remember much. We were awoken by 4 guys with guns drawn yelling at us to get out of bed. Turns out I was being raided by the friendly local drug task force. Sitting on the couch with my dad and this chick, whose name I could barely remember, while they tore up the house was interesting. We all ended up getting arrested and I haven’t talked to her since.


Family member after a wedding reception with an open bar. Can’t remember much as she can not either. But we both woke up in the nude with multiple used condoms all over the hotel room.

Written by Laura McNairy

Laura is a freelance writer for TFLN. She likes to write about what she knows best — dating, sex, and being awkward, but usually in the opposite order. She is the Assistant Editor and videographer for Peach Fuzz, a sex-positive nudie magazine in ATX.