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November 16, 2024 at 9:18am EST
Pete Davidson’s dating history is truly packed with A-list beauties. If there’s a beautiful, talented woman in Hollywood, chances are that she may be “Pete Davidson’s next girlfriend” — or at least that’s what it seems like these days. And truth be told, these pairings often leave us scratching our heads. We’re not denying Davidson is a talented and funny individual, but we’re dying to know how he ends up in long-term relationships with some of the biggest names in Hollywood, like Ariana Grande and Kim Kardashian, despite seeming to come from totally opposite worlds.
Related story Kim Kardashian & Pete Davidson Are Fueling Romance Rumors With This Confusing Photo
In a May 2021 interview with Breakfast Club Power 105.1 FM, Davidson talked about what he values most in his relationships. “I just off the top [tell them], ‘Hey, I’m nuts. Here are [sic] all of my issues. Here’s what I do. Here’s the therapist. That could either be a lot for someone, or they could be like, ‘Cool, that’s refreshingly honest.’ Or sometimes it can be a little intense and weird, and people can’t handle that stuff.”
He also added that he doesn’t have time for dating games because they “create this whole anxiety and a lot of stress, and there’s enough of that going on.”
Over the past few years, the Saturday Night Live alum has dated superstars, and every single time, it’s made headlines. Check out this slideshow to learn more about Pete Davidson’s confusing dating history, from Outer Banks star Madelyn Cline, Kim Kardashian, Kate Beckinsale, Cindy Crawford’s daughter Kaia Gerber, and more.
A version of this article was originally published in Nov. 2021.
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Madelyn Cline (Sept 2023-July 2024)
Image Credit: Photo by Eugene Gologursky/Getty Images for MTV.
One month after his split from Chase Sui Wonders, Pete Davidson has reportedly moved on with Outer Banks star Madelyn Cline. An insider recently told Us Weekly that “Pete and Madelyn are dating!”
Since then, they were seen on lowkey dates together, but as of July 2024, per The Sun, they have called it quits in an “amicable” breakup.
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Chase Sui Wonders (Dec. 2022- Aug. 2023)
Image Credit: Sean Zanni/WireImage
Right when fans were expecting more sightings of Pete Davidson and Emily Ratajkowski together, the SNL alum was seen with someone else at a New York Rangers game on Dec 15: his Bodies, Bodies, Bodies costar Chase Sui Wonders.
After claiming they were just friends at first, the two started dating and seemed to be hitting it off (they even bought a dog together!) before sources claimed the two split in August.
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Emily Ratajkowski (Nov. 2022-Dec. 2022)
Image Credit: Marc Piasecki/WireImage
After much speculation about who Pete Davidson would date after his split from Kim Kardashian, the former Saturday Night Live star was spotted on a date with none other than newly-single model Emily Ratajkowski.
The claims went viral after Deuxmoi, a celebrity gossip user on Instagram, shared an Instagram Story of someone spotting the two together. “EMRATA AND PETE DAVIDSON ON A DATE TOGETHER HOLDING HANDS AND ALLLL” the Deuxmoi follower claimed, adding, “his hands were alllll over her and they’re clearly hooking up.”
The two then made their first joint appearance at a New York Knicks basketball game at Madison Square Garden but haven’t been seen together since.
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Kim Kardashian (Oct. 2021-Aug. 2022)
Image Credit: Priscilla Grant/Everett Collection.
It all started with some confusing pictures at Knott’s Scary Farm, then led to a secret rendezvous — and it led everyone to be confused. But after some time, they admitted that they were dating and absolutely smitten with one another. They went on vacations together, went to high-profile events like the Met Gala, and truly seemed like they were going to go the distance. However, on Aug. 5, 2022, news broke that the pair decided to split after nine months together.
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Phoebe Dynevor (Feb. 2021-Aug. 2021)
Image Credit: Elizabeth Goodenough/Everett Collection
Arguably one of the most confusing hookups of 2021 was between Bridgerton’s Phoebe Dynevor and Pete Davidson. They were seen getting snuggly at Wimbledon and seemed as happy as can be. However, their busy work schedules and long-distance go to them and they broke it off.
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Kaia Gerber (Oct. 2019-Jan. 2020)
Image Credit: Kristin Callahan/Everett Collection.
Kaia Gerber and Pete Davidson had the classic friends-before-lovers kind of relationship, and rumors were fueled soon after Davidson was seen leaving Gerber’s apartment. But it seems like friendship was more in the cards for the pair, as they called it quits less than three months later.
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Margaret Qualley (Aug. 2019-Oct. 2019)
Image Credit: James Atoa/Everett Collection.
Sparks flew immediately between Pete Davidson and Margaret Qualley, but the relationship ended just as quickly as it started. Neither of them took long to start dating again, with Qualley going on to date Shia LaBeouf shortly thereafter.
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Kate Beckinsale (Jan. 2019-April 2019)
Image Credit: Photo by Michael Buckner/Variety via Getty Images.
Pete Davidson took a bit of a break from the dating game, but not too long after his split from Ariana Grande, he was seen making out with Kate Beckinsale. People had some strong, confusing opinions about the pair’s age difference, but neither of them cared about the scrutiny. But the pair didn’t last too long and they ended up calling it quits in April.
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Ariana Grande (May 2018-Oct. 2018)
Image Credit: Photo by Stephen Lovekin/Variety/Penske Media via Getty Images,.
Ariana Grande and Pete Davidson’s whirlwind romance was the biggest topic of 2018 — mainly because everybody had so many questions. They started dating in May 2018 and within one month, they got engaged. Then they got matching tattoos, wore matching costumes, said their love was transcendent — but ended up calling it quits in Oct. 2018.
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Cazzie David (2016- May 2018)
Image Credit: Photo by Michael Buckner/Variety via Getty Images.
Umbrella Academy actress Cazzie David and Pete Davidson started dating back in 2016 and kept their relationship on the down-low. However, Davidson reportedly broke up with David over text message — and soon started dating Ariana Grande. David released a book exposing her relationship with Davidson in 2020.
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Carly Aquilino (2015)
Image Credit: (Photo by Jeff Kravitz/FilmMagic.
Back in 2015, Pete Davidson and Carly Aquilino met on the set of Girl Code, and sparks flew immediately. They dated throughout the year at the beginning of both of their careers, but they called it quits after a year. But no worries, they’ve stayed good friends, and she even appeared in his film, The King of Staten Island.
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