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

April 14, 2025 by Alison Campbell

#19: Parallel Parking

Parallel parking doesn’t come easily for everyone, this guy included. This guy asked his date to wait outside while he parked the car, and after three failed attempts, he decided to give up and drove off, leaving his date on the curb. Since he was a ride, not only was her date night ruined, but she had to walk home. It’s a good thing she lived nearby!

After three failed parking attempts, this guy was probably too ashamed to look his date in the eye. Besides, this whole parking fiasco is a real mood-killer; who would be in the mood for a date after something like this happens? And most of all, he probably realized he wasn’t going to make this parking, and he was in over his head, so he decided to simply avoid the humiliation and drive off.

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Filed Under: Funny, lznimport2 Tagged With: infiniteScroll

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