Article created by: Austėja Akavickaitė

“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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Screenshot of a Twitter post sharing one of the worst first date stories submitted for Jimmy Fallon's challenge.

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    Screenshot of a tweet sharing one of the worst first date stories where a man used a lint roller on clothing before a date.

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    #3

    Tweet about a worst first date experience involving a warrant and jail, shared for Jimmy Fallon's challenge.

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    #4

    Tweet sharing a worst first date story about an unexpected family reunion introduction on a blind date challenge.

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    #5

    Tweet showing a worst first date story where the guy assumed marriage and family details prematurely.

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    Tweet showing a personal story about a worst first date involving eating chili dogs from a backpack in bed.

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    Tweet screenshot showing a user sharing a worst first date story about an awkward gas station moment.

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    Tweet by user Jacks sharing a worst first date story about someone picking scabs and flicking them on the table.

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    Tweet showing a humorous worst first date story about awkward moments shared for Jimmy Fallon’s challenge.

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    #10

    Tweet about worst first date experience where the person met someone unaware he was married, shared for Jimmy Fallon challenge.

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    #11

    Tweet by Jane Norris sharing one of the worst first date stories involving a gun request on social media.

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    #12

    Tweet screenshot of a worst first date story about a mistaken steak order submitted for Jimmy Fallon's challenge.

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    #13

    Tweet showing a story from the worst first date challenge about pouring wine on a first glass during a date.

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    #14

    Tweet about a worst first date experience at an underground swingers bar shared for Jimmy Fallon's challenge.

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    #15

    Tweet screenshot showing a worst first date story where a guy brought his mom after months of pressure to go on a date.

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    #16

    Tweet sharing a worst first date story about a confusing proposal in a mall food court during a challenge on social media.

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    Tweet showing a worst first date story where the date ate BBQ sauce with a spoon during dinner at a restaurant.

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    #18

    Tweet showing a submitted worst first date story for Jimmy Fallon’s challenge about awkward dating experiences.

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    #19

    Tweet sharing a worst first date story about a man upset over ladies night, part of Jimmy Fallon's challenge submissions.

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    Tweet showing a worst first date story where the person waited silently in a security car, leading to no second date.

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    #21

    Tweet showing a humorous worst first date story submitted for Jimmy Fallon's challenge on Twitter.

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    #22

    Tweet about a worst first date experience shared during Jimmy Fallon's challenge, detailing awkward and uncomfortable behavior.

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    #23

    Tweet sharing a worst first date story where a family discovers the couple are actually cousins after a Google search.

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    Tweet sharing a worst first date story about an awkward ride with strangers and a quick exit from the situation.

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    #25

    Tweet from Meredith Webber sharing a worst first date story about a date discussing war and national pride.

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    #26

    Tweet screenshot of a worst first date story where a person hid in a closet as their date tried to break in.

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    Tweet screenshot of a submitted worst first date story involving a bizarre conversation about languages and heritage.

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    #28

    Tweet by Meredith Lee sharing a worst first date story about a temper tantrum at In-N-Out during a date.

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    Tweet with a worst first date story about a surprising health confession during dinner, shared for Jimmy Fallon's challenge.

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    #30

    Tweet from Ms. Young Professional replying to Jimmy Fallon with hashtag Worst First Date sharing a humorous first date story.

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    #31

    Tweet showing a worst first date story about a night spent flirting with a sister, shared for Jimmy Fallon's challenge.

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    #32

    Tweet from Anthony sharing a worst first date story about taking a vegetarian to Buffalo Wild Wings.

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    #33

    Tweet by user @123yeswhy sharing a funny worst first date story with hashtag WorstFirstDate on social media.

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    #34

    A tweet sharing a funny worst first date story involving a Rolling Stones music comment from Jimmy Fallon’s challenge.

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    Tweet showing a worst first date story where a man asked for chocolate milk on a date, part of Jimmy Fallon's challenge.


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