Awkward First Date Stories

Below are a collection of stories from real women and men about their awkward first dates. We’ve all been there, whether it’s a blind date, you met online or you met this person previously, that first date was real awkward. Learn about first date tips from our post on avoiding awkward first dates.

Want to share your awkward first date story? Submit through our contact or tweet us @RomanticalAid with the hashtag #AwkwardRomance

Arm touching at the drive in: I was once set up with one of my close friend’s older brother. He seemed pretty cool, plus he was in college and I was only a high school senior. Ooo la la. We went to the drive in with a group of people and he set up our chairs on the other side of the car so we would be alone. Okayyy. Then he sat so close our arms touched for the whole movie. I didn’t really notice but he sent me a 500 word Facebook message later that night asking if the “arm touching” was too much.

-Single Senior in Michigan

Cheek to Cheek: I was real close friends with a guy I worked with at my summer job and we had a great time whenever we would hang out. I didn’t really find him attractive in that way but I guess I missed the boat when he asked me to the movies. I hadn’t realized he meant it as a date since we’d been hanging out so much. We arrived and he gave me a weird look when we sat down to the movie. After the movie he was my ride home, so imagine my shock at when he dropped me off and leaned in for a kiss, I didn’t really know what was going on so somehow we ended up rubbing cheeks. Eeesh.

-Clueless in Wisconsin

 Propositions from Tinder: When I was in college I went on a tinder date with a boy that was from Utah. We met for dinner and the date went pretty well, I thought. At the beginning of the date he let me know he was Mormon, which is fine. Then at the end of the date he tells me, albeit awkwardly and ashamed that he’s engaged to be married and he wanted to get some “tips on how to please his wife.” My mouth was about on the floor, when I said “you want to have sex with me?!” At which point he freaked out and said “No, no no penetration, but everything else…” I was shocked. And why me? I promptly threw my drink at him and left.

-Not a teacher in California

 It was hot, really hot.  I went on a date back in college that probably would have been mostly unmemorable, except for one detail. We had gone out to a Mexican restaurant for dinner and I was really into talking and paying attention to my date. We both had burritos (very classy) and I squirted a bunch of hot sauce on mine without really noticing. After a few bites my entire mouth and face was on fire and I could hardly talk. I drank my drink, my dates drink and gestured wildly to the waiter to bring more fluids. He came back with celery, which surprisingly, tempered the burn. I was so embarrassed, my date seemed slightly disgusted. Hot stuff, it happens, even on the first date.

-Keeping it hot in Ohio