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Celebrity Dating Horror Stories: Ariana Grande, Khloe Kardashian and More Dish on Bad Dates

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Mar 12, 2025 4:00 pm·

By Katherine Schaffstall

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Celebrity Dating Horror Stories: Ariana Grande, Khloe Kardashian and More Dish on Bad Dates

Ariana Grande: A Nosebleed Nightmare

Even the most popular girls aren’t immune to courtship catastrophes. “I got a nosebleed on a date once,” Ariana told Girls Life, noting the timing couldn’t have been worse. “He was about to kiss me!” Luckily the fella was “nice about it,” she added. “He drove me to CVS and bought me Wet Ones.”

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Khloé Kardashian: The Case of the Bed Wetter

During their first adult sleepover, one of Khloé’s past love interests did something shockingly childish. “He wet the bed. Just wet the bed,” the reality star confessed on her “Khloé in Wonder Land” podcast. “I was like, okay, that’s weird.” The duo didn’t discuss the embarrassing incident, so Khloé, 40, thought maybe she’d just imagined it … until the next time the guy spent the night and it happened again! “So he was a pee boy,” she recalled. “We don’t need pee boys.”

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Billie Eilish: Dissed Her Kiss

Talk about a “Bad Guy.” On a movie date when she was 13, Billie’s suitor gave her a smooch and then proclaimed: “‘That was not as magical as I thought it would be,’” the singer, 23, revealed to The Howard Stern Show listeners. The “super rich” brat had his butler take him home. “He left, and I was stuck there,” Billie dished. “No one told me they were going to leave!”

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Tiffany Haddish: Caught In a Spin Cycle

Domestic blitzed! “I went on a date with a guy to wash his clothes,” the Nobody’s Fool star told TMZ. “He said we were going to dinner, and we got dinner, and then we went to the laundry house and washed clothes.” Tiffany, 45, didn’t get into specifics about what exactly his dirty load included, but noted she’s not anyone’s “maid.”

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Mindy Kaling’s Mixed Signals

Dine and dashed hearts! The Velma alum went out for a meal with a guy she was “really attracted to.” Alas, the feelings weren’t mutual. “On the date, it became apparent that it wasn’t a date,” Mindy, 45, shared on Reddit. “He was just a straight dude who was psyched to have dinner with me in a platonic way. He talked about an actress he really wanted to date and we split the check.”

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Awkwafina’s Cozy Meal Gone Wrong

Among the things not to do on a blind date with Awkwafina? Order without consulting her first. “He was like, ‘We’ll take the steak.’ One steak, for both of us,” the 36-year-old complained to Vogue, adding that Mr. Wrong wanted it well-done. “Who eats a well-done steak? That’s like eating a bed.”

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