Pete Davidson’s Dating History: Ariana Grande, Kaia Gerber, Kate Beckinsale and More!

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Pete Davidson’s Dating History: Ariana Grande, Kaia Gerber, Kate Beckinsale and More!

From on-again, off-again relationships to whirlwind engagements, Pete Davidson has had a rocky dating history.

Following a brief engagement to Ariana Grande in 2018, Davidson didn’t turn his back on romance with fellow A-Listers.

Davidson began romancing actress Margaret Qualley several months later until October 2019 before he rebounded with the likes of Kaia Gerber and Phoebe Dynevor.

Nearly three years later, Davidson met Kim Kardashian in October 2021 during her hosting gig on Saturday Night Live. “They have such a strong connection,” a source exclusively told Us Weekly in November 2021. “She gets butterflies around him and he makes her laugh — and that’s more than she can say for other guys.”

Davidson and Kardashian’s romance ultimately fizzled in August 2022 after nine months together, but Davidson wasn’t single for long. He moved on with the likes of  Emily Ratajkowski and Chase Sui Wonders.

Scroll down to see who Davidson has dated:

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Carly Aquilino

The comedian and the Girl Code star casually dated in 2015, according to Complex. She seemed to address his engagement to Ariana Grande in June 2018 via Instagram after posting a screenshot of a cryptic text message she received reading, “I know I’m the 9 billionth person to text you today about this, but… I can’t.”

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Cazzie David

Davidson and the Eighty-Sixed creator started dating in May 2016 and split two years later, officially ending their on-again, off-again relationship in early 2018. “I’m very lucky. She’s very, very supportive,” he told Entertainment Tonight in September 2017 of David.

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Ariana Grande

Just weeks after they started dating, Us exclusively revealed in June 2018 that Davidson and Grande got engaged. However, the duo broke off their whirlwind engagement that October.

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Kate Beckinsale

Davidson and the Pearl Harbor actress sparked romance rumors at the Golden Globes in January 2019 after they were spotted flirting at an afterparty. “She was following him around a bit and waiting for him,” an insider exclusively told Us at the time. “People approached her and she didn’t want to talk to anyone else.” The pair's fling ended in late April 2019.

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Margaret Qualley

Us broke the news of the Dirt actor’s relationship with the Once Upon a Time in Hollywood star in August 2019. “They’ve been seeing each other for a couple of months and Margaret is really excited about him,” a source told Us.

Two months later, Us exclusively revealed that the pair’s whirlwind romance was over.  

“They remain friends,” an insider close to Davidson and Qualley told Us in October 2019.

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Kaia Gerber

Us exclusively confirmed that Davidson was dating the 18-year-old model in November 2019. “Pete and Kaia are dating and they’ve been trying to keep their relationship somewhat low profile,” the insider revealed. But weeks after the comedian joked in a December episode of SNL that he was headed back to treatment for mental health issues, they split. The New York Post's Page Six confirmed the breakup on January 14, 2020.

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Phoebe Dynevor

Us broke the news in April 2021 that the comedian swept the Bridgerton star off of her feet. "They're happy with each other," a source explained at the time, adding that the duo were "seeing where their relationship goes" and "trying to make long distance work." Later that month, Davidson and Dynevor were photographed cuddled up together on a scenic walk in the U.K. However, Us confirmed in August 2021 that they called it quits. 

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Kim Kardashian

The Keeping Up With the Kardashians alum was originally linked to the comedian after they worked on several sketches together during her hosting gig on SNL in October 2021.

After the twosome were seen together on multiple occasions, a source told Us that Kardashian is "falling for" the comedian, who "makes her laugh" and "feel good."

Although the makeup mogul and Davidson played coy about their relationship status, they held hands during a public outing one month after sparking romance rumors. Us confirmed in August 2022 that the duo had called it quits. “There truly wasn’t drama between them when they decided to separate,” the source exclusively old Us at the time. “It was something they talked through; it wasn’t a sudden breakup.”

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Olivia O’Brien

In June 2022, the singer claimed that she briefly dated Davidson before his romance with Dynevor. "He texted me and was like, 'I'm seeing someone else. So, like, I can't,'" she said about their split on the "BFFs with Dave Portnoy, Josh Richards, and Brianna Chickenfry" podcast.

At the time, O’Brien noted that the duo have remained on good terms. "He's hot and he's really funny. And he's really sweet. He's a really sweet guy," she gushed about her ex-boyfriend.

A rep for the comedian, however, told Us, "There is no truth to this — they were friends and hung out one time."

In July 2022, the singer clarified via her Instagram Story that her answer to a “very specific question” was taken “out of context." She wrote, “I never claimed to date anyone. Stop trying to start weird drama over me texting someone 2 years ago.”

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Emily Ratajkowski

Us confirmed in November 2022 that the two were casually dating. “Pete and Emily have been talking for a couple months now,” an insider exclusively told Us at the time, adding that the duo were “in the very early stages, but both really like each other.”

They were set up by mutual friends. "Pete makes Emily laugh and he loves how intelligent she is,” the source added.

Us confirmed in December 2022 that the duo amicably split after dating for less than two months.

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Chase Sui Wonders

Following Davidson’s brief romance with Ratajkowski, the actor sparked romance rumors with his Bodies Bodies Bodies costar in December 2022. The twosome were spotted on several outings together before enjoying a getaway in Hawaii one month later.

After less than one year of dating, the pair called it quits in August 2023. “There's no bad blood or any hard feelings between them,” a source exclusively told Us at the time. “Their relationship had simply run its course and they decided they just wanted different things.”

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Madelyn Cline

Us broke the news in September 2023 that Davidson had started dating the Outer Banks actress.

“They spent the night together at the Beverly Hills Hotel and then had breakfast together there the next morning,” a source told Us at the time. “They were really low-key and kept things casual, wearing baseball hats.”