25 People Who Had Seriously Awkward One Night Stands


The previous night was valentines day. I had just been dumped by a long term boyfriend. I was drunk in walgreens looking at the flowers and chocolates thinking about my ex. I then decided it would be a good idea to buy him a balloon and some flowers and leave it outside his house, because these are the kind of brilliant ideas I get while drinking. Got outside, let go of the balloon and it flew away, started crying. Some dude in his car asked me what was wrong. Woke up next morning. He started telling me about how he was trying to be a rapper, made me listen to some really bad stuff he had wrote. I had to get out. Get up to leave, tells me I have to wait until his grandma leaves the house to play bridge with her buddies, because he lives with her since he cant afford to live on his own. I finally get to leave after a couple hours of extreme uncomfortable and awkward feelings of regret. As I walk out, I see his grandma had put the flowers I bought in a vase on the table.


Came home with a girl from the bar. We were both trashed, had sex, her dog watched. She vomited on me while performing oral sex. Cleaned up as best as I could before passing out. Woke up in the morning to her mom attempting to come in, asking who was in her room. She said “no one, go away” before telling me that I couldn’t leave until her parents left for work. No way in hell I was staying for two hours with puke dick. I climbed out her window on the second floor and jumped off of the roof. Stuck the landing and jogged away down the street… into a culdesac. Turned around to get out and her mom is on the front lawn in a bath robe staring me down holding her morning coffee. Walked to a gas station where a friend picked me up. Oh, and I got chlamydia.


I was house sitting for my dad who was out of town for a week. Had a girl over who I’ve known for 6 years, and my dad was pretty involved at my old high school so he knew her too. He came home a day early, and found us both naked in my old bed. He thought it was hilarious, the girl and I were both mortified.


We spent the night together at a party. We woke up reminiscing of the night before. He walked to the gas station to get us drinks and snacks. I had bubble guts so I farted one time, it smelled like death; he came back maybe 10 minutes later and it still reeked and he started yelling about dog shit, woke everyone in the house up. He still doesn’t know it was me.


I woke up to her wheelchair-bound husband pointing a gun to my face. Damn cougars.

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.