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40+ Absurd, Awkward, and Cringy First Date Stories Shared by Jimmy Fallon’s Audience

February 17, 2026 by Lliane Hunter

This article was originally published on petsreporter.com

We all have to kiss a few frogs before we find our prince. And let’s be honest; first dates are almost always awkward, uncomfortable, sometimes boring, and other times downright cringy. Jimmy Fallon challenged his fans to share their funniest, most embarrassing, and cringe-worthy first date stories. You might find it hard to believe, but many of these stories, as funny as they seem, ended in a happily ever after.

#1: Multi-Tasking

I always thought this kind of stuff only happens in the movies, but I guess I thought wrong. This woman was out on a date on which her date was on a date with another woman! He was on two dates at the same restaurant simultaneously. I’m sorry, but this is as sleazy as sleazy gets.

When you’re on a date and your date goes to the restroom a lot or finds other reasons to disappear every couple of minutes it’s definitely a red flag, but what woman would imagine that her date is on another date? It’s a good thing this waiter told her what’s going on so that she could get up and leave.

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Filed Under: Funny, lznimport2 Tagged With: infiniteScroll

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