50 “Worst First Date” Stories That People Submitted For Jimmy Fallon’s Challenge

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“It’s Hashtags time!” Jimmy Fallon’s collections of hilarious real-life stories are back with a bang. Twitter users are having lots of fun sharing their personal stories with the 46-year-old comedian and the host of The Tonight Show. This time, everyone’s opening up about their very worst first dates by posting under the #WorstFirstDate hashtag.

First dates are supposed to be a tad awkward but fun. Unfortunately, that’s an overly romantic view of them. Reality shows us that first dates can be utter disasters—as bad as they are hilarious! Take a look at our collection of the funny and unbelievable stories that Twitter users shared with Fallon, give the ones that grabbed your attention an upvote, and share your own stories in the comment section.

Having a weird feeling of déjà vu? When you’re done with this list, check out our post about Fallon asking his fans the very same question nearly 3 years ago. Time flies, but people will never stop going on dates, so there’s an inexhaustible supply of future awkwardness.

Mike Sington, a former senior executive at NBCUniversal and a celebrity and pop culture expert based in Los Angeles, detailed to Bored Panda how shows like Fallon’s work, how late-night shows have been adapting to the pandemic, and what the purpose of hosts asking questions on Twitter is. Check out what he had to say below.

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