25 People Who Had Seriously Awkward One Night Stands


A guy I took home from a bar, whom I had previously met before multiples times, left $200 on the bed side table. I found it when I woke up. Attached was a note that just said ‘thanks.’ I am not a hooker by any means and didn’t ‘perform’ anything out of the ordinary. It was weird. But it paid my electric bill so I didn’t complain.


There was a continental storm and she was snowed in until 5pm the next day.


Woke up to a bunch of snapchats of my penis from the girl I slept with. She put a couple of them on her story. I guess she did this when I was asleep?


Her asking, “Sooo….what are we now?”


Went to an older lady’s house one night. Next morning her kid comes in, and he’s at least 16-17. He’s like, ‘omg mom, another one??’

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.