25 People Admit The Most Embarrassing Thing That Has Ever Happened To Them


Back in middle school when AIM was a big thing, I was chatting with a girl I had a crush on. She had a hispanic last name. Anyway, I wanted to send her something I thought was funny. So I did the old CTRL+V and pressed enter in the same motion without checking it first. Apparently, the last thing I had on my clipboard was As you may infer from the name, yeah, it’s porn. Oddly context-specific porn. I tried to scramble and think of an excuse. There was none. I think I said “oops, wrong link, no need to click that.” May have blamed a computer virus. That sounds like something I would do. Then I just closed the application in a panic. Based on her behavior the next day, she absolutely clicked that link and absolutely didn’t think it was a virus.


When I was about 17 or so I was at my wealthy girlfriend’s house on a lazy summer afternoon. It’s just me and her in their giant house, and my girl decides to take a shower. I’m in her room, pretty bored, when I decide to investigate her underwear drawer. I find a tiny, sequiny, pink thong and decide it would be funny if my 200 lb (well built at the time) self surprised my girl by wearing them. I hear the shower turn off, and a minute later, I hear someone coming down the hallway. I start strutting down the hallway, naked but for this tiny, shiny thong, my mediocre dick and giant balls hanging out of one side of it. And then she sees me. She, the South American housekeeper. I hear half of her frightened gasp before I turn and run back into the bedroom. I avoided this poor woman for the next two years of my relationship with this girl.


Fainted in a high school psych class while watching a video of brain surgery. Apparently I just fell out of my desk like a sack of bricks. Woke up on the floor and everyone was freaking out/staring at me.


I once shared someone’s photo on Facebook. I wasn’t friends with him on Facebook, I fancied him, and the photo was shared on my profile for 10 hours before I noticed. I rarely facebook stalk people now.


First date with this girl, we went exploring in the woods on a 90 something degree day. I didn’t eat prior to the date because I was afraid of getting nervous and throwing up. Eventually we made it out of the woods where there were more people and I threw up. Made it a few feet and then threw up again.

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.