Celebrity Dating Disasters: Ariana Grande, Charlize Theron and More Stars Reveal Their Worst Dates

Ariana Grande was about to have a steamy moment with her then-beau when she suddenly experienced a minor health issue.

"I got a nosebleed on a date once," she told Girls Life. "And just as he was about to kiss me! He was nice about it. He drove me to CVS and bought me Wet Ones."

In a Vogue "Sad Hot Girls" video, Awkwafina pointed out a dining habit her blind date broke in the past.

"The waitress comes and I'm about to order, and he was like, 'We'll take the steak.' One steak, for both of us," said the Crazy Rich Asians actress. "And then he says, 'I want it well-done.' I was like, 'How dare you? Who eats a well-done steak?!' That's like eating a bed. The steak comes, and he proceeds to cut up the steak into baby pieces, like one would do for a small bird."

During an appearance on The Howard Stern Show, Billie Eilish opened up about the time her suitor kissed her while on a movie date when she was 13.

"[And] then he said, 'That was not as magical as I thought it would be,'" she shared. "He was super rich, and his butler — literally his butler — [took him home]. He left and I was stuck there, no one told me they were going to leave … Dude is h---- ugly now."

Even Charlize Theron had a dating horror story to tell.

In her 20s, the Hancock star had a "lovely" dinner with a "super handsome" guy who made an eyebrow-raising request before their date ended.

"And he drove me home and I signaled I was in for a kiss...He pulled over by my house and we started kissing and it was really good. And then he pulled away and he whispered, 'Make out with my nose,'" Theron said on Jimmy Kimmel Live!.

While she gave him a little peck on the nose, her date reportedly insisted she should "make out" with it.

In an episode of her eponymous talk show, Drew Barrymore opened up about her first date and recounted why she later thought the man was "going to murder" her.

"I knew a lot of people who knew him, so it felt safe, right? That feels safe," she told her viewers. "And he was really cute, and I was like, 'Okay.' And he's like, 'Come to my apartment,' which, I -- again, if I didn't know people who know him, would have never done. Ever."

After noticing a "giant" roll of clear plastic, she told the man she needed to go back upstairs.

"You know, I know we don't really know each other, but I was really afraid that you were going to murder me,'" Barrymore told her date.

While their relationship did not progress, the awkward moment reportedly helped them to "bond" as friends.

Justin Bieber had an embarrassing dating disaster when he was 16.

"I was on a date at King's Buffet. I got spaghetti and meatballs, which wasn't a smart thing to do. I spilled it all over me," the "Baby" singer said. "She never went out with me again."

Kelly Clarkson recalled having a dinner with a former suitor at Bennigan's, where the man talked about his height "for, like, a solid hour."

"I withstood an hour. And then I went to the bathroom … and I left," she revealed on The Ellen DeGeneres Show.

Speaking about one of the worst dating mishaps she ever had, Khloé Kardashian disclosed she once dated someone who "slept over and he wet the bed."

"And I was like, okay, that’s weird, obviously. Cause we’re adults," she remembered on her "Khloé in Wonder Land" podcast. "He never addressed it, we never talked about it, I was like, okay, maybe this didn't happen, because we didn't talk about it."

Mindy Kaling had the chance to go out for a meal with a guy she was "really attracted to," though the feelings were not mutual.

"On the date, it became apparent that it wasn't a date," she 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."

"I went on a date with a guy to wash his clothes. He said we were going to dinner, and we got dinner, and then we went to the laundry house and washed [his] clothes," Tiffany Haddish said on the man she dated in an interview with TMZ.

When the reporter said it didn't sound that bad, Haddish responded, "That's horrible. I'm not no d--- maid."