Pete Davidson’s Romantic History: From Ariana Grande Engagement To Rumored Phoebe Dynevor Romance

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Take a look back at Pete Davidson’s relationships. From his nearly two-year romance with Cazzie David to whirlwind engagement with Ariana Grande, and more!

Pete Davidson rose to fame as the young, millennial cast member of Saturday Night Live. Over the years, he’s broken the internet with comedy specials, SNL sketches, and received well-earned praise for his work in films like The King of Staten Island. But with all of this success comes a lot of scrutiny — especially on Pete’s love life.

Over the years, the comedian’s relationships have been reported on countless times. But his relationships extend far beyond his recent whirlwind romances. Take a look at the guide below to learn more about the women Pete has dated throughout his young career.

Carly Aquilino

Pete Davidson, Carly AquilinoPete Davidson and Carly Aquilino dated in 2015 [AP].Pete’s first high-profile relationship came in 2015 when he began dating fellow comedian Carly Aquilino of MTV’s Girl Code. 2015 was a pretty big year for Pete, who was enjoying his second season on SNL. The pair didn’t really make headlines for anything that occurred in their relationship or their subsequent breakup later in the year. The two seem to have quite an amicable, friendly relationship since their split. Carly co-starred in the 2020 film The King of Staten Island, which Pete leads. She even took to Instagram on June 11 to thank Pete and director Judd Apatow for the opportunity to be a part of the project.

Cazzie David

Cazzie David, Pete DavidsonPete Davidson and Cazzie David were together for nearly two years [AP].Following his split from Carly, Pete had a nearly two-year relationship with Cazzie David. Cazzie is the daughter of comedian Larry David, who’s appeared on SNL a number of times. The two began dating in roughly May of 2016. In a recently published interview with The Los Angeles Times, Cazzie explained that the former couple was “infatuated” with one another. However, Cazzie confessed that she “struggled to convince him that she really loved him.”

The pair split in early 2018, but Cazzie admitted that she immediately regretted the decision. The writer revealed that she tried to get in touch with Pete and when he finally responded, he shared with her that he was “happier than he’d ever been,” and split from her for good over text. Pete quickly moved on to his next relationship, which will be explained in more detail below. But the high-profile nature of his next romance was something Cazzie really struggled with.

“It was a really pivotal moment in my life. And writing about it has caused me a ton of anxiety, especially because I talk so much about hating the attention it brought me. Why would I bring more attention to myself by writing about it? But there’s nothing that’s gonna be worse than what I already experienced with that,” she explained.

Ariana Grande

Pete Davidson, Ariana GrandeAriana Grande and Pete Davidson out in NYC on August 18, 2018 [MEGA].In May 2018, Ariana Grande and Pete took their romance public. The two had known each other for a number of years, as Ari appeared on SNL as the musical guest in 2016, during Pete’s early seasons on the variety sketch show. They got engaged in June 2018 after just a few weeks of dating. On Ari’s album Sweetener she wrote a song dedicated to Pete called “Pete Davidson.” The two also made a number of appearances on red carpets, and Pete was by Ari’s side to support her at various awards shows.

By October 2018, Pete and Ari called off their engagement. The relationship ended roughly one month after the death of Ari’s former boyfriend, Mac Miller, putting even more scrutiny on the young pop star. Ari, however, took the shocking split and used her art to get through the breakup. Her 2019 album Thank U, Next made a number of references to Pete.

In the title song and single “Thank U, Next,” Ari sings “Even almost got married/ And for Pete I’m so thankful,” referencing the SNL cast member. For his part, Pete only had kind sentiments for his ex-fiancée. He even used time during SNL‘s segment “Weekend Update” to wish her well. “She’s a wonderful, strong person, and I genuinely wish her all the happiness in the world,” he said during the November 2018 episode.

Kate Beckinsale

Kate Beckinsale, Pete DavidsonKate Beckinsale and Pete Davidson hold hands leaving the Motley Crue Show at The Whiskey A Go Go [BACKGRID].Pete began 2019 with a new relationship. He started dating actress Kate Beckinsale, who is roughly 20 years Pete’s senior. The pair were spotted out and about at various events, including a basketball game where a photo of the two making out next to Queer Eye‘s Antoni Porowski went viral and even got the meme treatment. During their time together, Kate also referenced their relationship in an interview with The Los Angeles Times.

“I’ve never been in this position before — never dated anybody who comes with their own bag of mischief,” she shared in March 2019. “It’s all quite shocking, and something to get used to. I think if you liked the person less, you would bow out of it. If that were the main thrust of the relationship, there would be a problem. But it’s not.” The two split one month later in April 2019.

Margaret Qualley

Pete Davidson, Margaret QualleyMargaret Qualley spotted with Pete Davidson in the streets of Venice on September 2, 2019 [MEGA].Near the end of the 2019 summer, Pete began dating Once Upon A Time…In Hollywood actress Margaret Qualley. In September, the two were spotted out and about during a date night in Venice. The romance was pretty short-lived, though. Margaret and Pete dated for only two months, splitting in October 2019.

Kaia Gerber

Pete Davidson, Kaia GerberPete Davidson and Kaia Gerber attend a friend’s wedding in Miami on November 23, 2019 [MEGA].One month after splitting from Margaret, Pete started dating model Kaia Gerber. The former couple was first spotted on a few low-key outings before they became more comfortable showing affection for one another in public spaces. The relationship, however, didn’t last very long. The two went their separate ways by January 2020. The comedian, though, had nothing but kind thoughts regarding Kaia.

During a February interview with Charlamagne tha God, Pete confessed that prior to their breakup he was “going through a lot.” Pete also said of Kaia that she is “beautiful, smarter than me…If anyone was worried that I was too smart or advanced for her, they do not have to worry at all. She was way, way smarter than I was.”

Phoebe Dynevor

Pete Davidson, left, at the March 2020 New York premiere of ‘Big Time Adolescence’ / Phoebe Dynevor, right, at the 73 rd British Academy Film Awards in Feb. 2020 (Shutterstock)

In early 2021, Pete Davidson was once again the subject of romance rumors. The SNL funnyman was supposedly “spending time” with Bridgerton star Phoebe Dynevor in her hometown of Altrincham, Greater Manchester on March 21. Pete was spotted out and about in the UK town and took pictures with fans. A month earlier, Phoebe reportedly spent time with Pete in Brooklyn while she was shooting for TVLand’s Younger.

The two didn’t immediately respond to the speculations, but a teenage British schoolgirl claimed she saw Pete and Phoebe “holding hands, hugging, and [acting] like they were a couple.” She also claimed that they “looked like they were in a relationship and they seemed happy together… I hadn’t seen anything written about Pete being in a relationship with Phoebe, but once I saw them together I thought, ‘Maybe they are?’… I ran up the road to catch up with them and asked him if he was Pete Davidson, and he answered in an English accent and joked he was trying to trick everyone that he’s English. He seemed quite happy and didn’t mind me taking a picture with him.”

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