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  1. Home
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  3. Yikes: Celebrities Worst First Date Stories EVER

Yikes: Celebrities Worst First Date Stories EVER

Allvipp Newsroom / June 27, 2024 - 05:05 am

1 / 10

Pinterest Warner Music Group Hosts Pre-Grammy Celebration In Association With V Magazine - Inside
(© 2018 Getty Images)

Kelly Clarkson

Kelly Clarkson's 18-year-old self endured a date where her date incessantly talked about their one-and-a-half-inch height difference. At 5'3.5", Kelly excused herself from the endless height discussion, sneaking off to ditch the date.

2 / 10

Pinterest Jenny Slate of 'The Sunlit Night' attends The IMDb Studio at Acura Festival Village on location at The 2019 Sundance Film Festival
(© Getty Images)

Jenny Slate

Jenny Slate's friend-set date took a strange turn when her date arrived, without previous warning, dressed as a knight. The "humiliating" experience involved chainmail clinking during dinner, making it clear it wasn't a match. "His chainmail [was], like, getting caught on stuff. ... He's trying my pasta with the chainmail clinking across."

3 / 10

Pinterest "Mad Max: Fury Road" Photocall - The 68th Annual Cannes Film Festival
(© 2015 Getty Images)

Charlize Theron

Charlize Theron's awkward encounter in her 20s took an unexpected turn when her date asked her to make out with his nose after a seemingly great dinner. Uncomfortable, Charlize shared this cringe-worthy story on Jimmy Kimmel Live.

4 / 10

Pinterest World Premiere Of Barbie - Arrivals LOS ANGELES, CALIFORNIA - JULY 09: Billie Eilish attends the World Premiere of Barbi
(© IMAGO/Avalon.red)

Billie Eilish

At the age of 13, Billie Eilish experienced an unmagical movie date when her date, dissatisfied with the kiss, was chauffeured home by his butler, leaving Billie alone. The boy who kissed her said, "That was not as magical as I thought it was gonna be."

5 / 10

Pinterest Jenna Bush and Barbara Bush.
(© IMAGO / ZUMA Wire)

Jenna Bush and Barbara Bush

Jenna Bush Hager's worst date involved her now-husband Henry and the Secret Service. The date took a bizarre turn when Henry's car ran out of gas, went backward, and hit the Secret Service. Despite the mishap, they ended up falling in love.

6 / 10

Pinterest 95th Annual Academy Awards - Arrivals
(© 2023 Getty Images)

Mindy Kaling

Mindy Kaling's excitement for a dinner date turned into confusion when she realized it wasn't a date at all. The guy turned out to be a straight friend who discussed his interest in another actress, leaving Mindy to split the check.

7 / 10

Pinterest Selena Gomez in a mini dress
(© IMAGO/ABACAPRESS)

Selena Gomez

Selena Gomez and Nick Jonas' attempt at a private date didn't go as planned. Jonas suggested standing 25 feet apart during a Central Park outing, leading to an uncomfortable experience for Gomez. "She was unhappy that her Central Park experience was ruined by the fact that I walked about 20 feet away from her, even though they were taking pictures of us and obviously we were there together," Jonas said.

8 / 10

Pinterest Emma Watson Harry Potter Hermione Granger
(© Getty Images / Jamie McCarthy)

Emma Watson

Emma Watson's worst date involved a guy expressing his inability to be friends with people he deemed unattractive. A shocking revelation that instantly put an end to any romantic prospects.

9 / 10

Pinterest Dove Cameron Descendants Singer Breakfast
(© IMAGO/PA Images)

DoveCameron

Dove Cameron faced a bizarre situation when her date got upset over a sweet note from the waitress, proclaiming her as "sunshine." Apparently, he wanted the spotlight on him, not on Dove.

10 / 10

Pinterest Kirsten Dunst Reveals She's Confused About Being Included In Kanye West's Campaign Poster
(© Getty Images)

Kirsten Dunst

Garrett Hedlund's attempt at romance with Kirsten Dunst involved a 3 a.m. canoe ride. Unfortunately, the canoe flipped, leaving them swimming back in less-than-ideal conditions, yet they went on to date until 2016.

Embarking on the journey of love is a universal experience, and even celebrities are not immune to the cringe-worthy, awkward moments that can unfold on a first date.

Celebrity Worst First Date Stories

Despite their fame and fortune, stars too have stumbled through encounters that make for unforgettable and often amusing tales. In this article, we delve into the world of celebrity romance, shedding light on the worst first date stories that even the rich and famous couldn't escape. From unexpected mishaps to hilarious misadventures, get ready to witness the less glamorous side of celebrity dating.

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