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!

Been there, done that! From on-again, off-again relationships to whirlwind engagements, Pete Davidson has had a rocky dating history. The Saturday Night Live star has had his fair share of ups and downs as the world watched him romance Ariana Grande for months and flirt with Kate Beckinsale at a 2019 Golden Globes party. Davidson is open to finding love again after experiencing many highs and lows. In December 2018, a source exclusively told Us Weekly that the stand-up comedian was “in a good place and he’s happy,” adding, “He’s not in a rush [to find love]. He’s focusing on himself and the future.” A few months later, however, Davidson began romancing actress Margaret Qualley. The twosome called it quits in October 2019 and he moved on with model Kaia Gerber before they split in January 2020. The following year, Davidson sparked romance rumors with Phoebe Dynevor after they were spotted spending time together in the U.K. in March. Us subsequently confirmed that the pair were officially dating. "Pete and Phoebe are still going strong despite not being able to physically spend time together," a source revealed to Us in April while Dynevor was filming her hit Netflix series Bridgerton. "They keep in touch over text and FaceTime. Right now, they're just focused on work. ... They're not looking to rush things." At the time, Davidson opened up about how he looks to be the "best" version of himself in his relationships. "I'm just very, very honest," he said during an interview on The Breakfast Club in May 2021. "I think what a lot of people do is they try to put on — not even their best self — but almost a version of themself that they would like to be. And eventually, that will unravel, you know?" [jwplayer gA9T5s3Z-zhNYySv2] The King of Staten Island actor explained that he isn't into "playing any of the games" when it comes to his dating life. "Off the top, I'm like, 'Hey, I'm nuts. Here's all my issues. Here's what I do. Here's the therapists. This is what happens,'" Davidson added at the time. "And that can either be a lot for someone ... or they could be like, 'Cool, that was really refreshingly honest.' Or sometimes it can be a little intense and weird and people can handle that stuff." In August 2021, an insider confirmed to Us that Davidson and Dynevor decided to go their separate ways because distance "put a strain on the relationship." The New York native later made headlines when he was spotted spending time with Kim Kardashian. After the reality star hosted SNL in October 2021, the duo enjoyed some Halloween festivities together during a group outing in California. The following month, Kardashian and Davidson grabbed dinner together two nights in a row in New York. A source told Us at the time that the businesswoman and the Brooklyn Nine-Nine guest star "have a unique chemistry" following Kardashian's split from husband Kanye West. "They have such a strong connection," the insider noted in November 2021. "She gets butterflies around him and he makes her laugh — and that’s more than she can say for other guys." That same month, the Skims founder and the Meet Cute actor confirmed their romance when they were photographed holding hands after weeks of speculation. In August 2022, Us Weekly confirmed the pair split after nine months of dating. Scroll down to find out more about his relationship history!

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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 that the Set It Up actor and the “God Is a Woman” songstress 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.

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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 pair were spotted packing on the PDA during a trip to Universal Studios one month later.