25 People Confess The Most Awkward Situation They’ve Ever Been In


At my old job I was covering the front counter while my coworker was on lunch. This girl comes up and indicates that she’s deaf and she writes her question to me. We had a sizable deaf population at this school so it wasn’t that unusual. We go back and forth exchanging notes and then my coworker comes up and starts asking this girl questions out loud. I’m like, “no, she’s deaf.” Then my coworker tells me, “oh she’s not deaf, she just can’t speak.” I felt like a huge idiot, super awkward, after passing notes back and forth when in reality I could have been talking this whole time and she could just write answers back to me. It was extremely embarrassing, but what the fuck was I supposed to assume!


I went on a first date to the movies. This was a day after a huge dilaudid binge and I realised 20 minutes in, I wasn’t feeling super great. I knew if I stood up, I’d pass out. Best of all, my date noticed I was breathing heavily and sweating so, without a word, I got up and lay down on the theatre floor and watched the movie like that for around 10 minutes.


When I was a teenager, I was at a drug dealer’s apartment. My boyfriend was in the back room with the guy, getting some weed, and I was in the living room, making awkward conversation with this woman who was there. I don’t know what she was on, but she was maybe in her 40s, but looked…bad. Years of drug abuse, whatever. Anyway, out of nowhere, she said, “My god. Don’t you hate it when a guy comes in your eye and the sperm think your eye is an egg and they try to break in?” Me: “….”


Once I was dating a girl who had her flirty sister stay over. They decided we could all sleep in one bed, with me in the middle. One had her hand on my chest on one had her hand down south. I thought that was the perfect time to try for a 3 way. I was wrong.


When I was a wee lad I was at Walmart with my mom and decided to see how I would fare as a blind person. We were standing at the register and I closed my eyes and started feeling around while my mom was behind me loading the conveyor belt with groceries. Well I thought I had spent a sufficient time Ray Charlesing it around so I went for a hug. During my time as a blind person I guess my mom performed a flawless spin move around me to where I hugged the lady standing right behind her. I was soon gifted with sight again and was horrified to not see my mom.

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.