Comedian Pete Davidson wasn’t exactly down and out when he began his short-lived but very public romance with Ariana Grande. While the tumultuous engagement made him a superstar, he was already sitting pretty as a Saturday Night Live cast member.
Unsurprisingly, Grande wasn’t the first famous woman to link up with Davidson. Here’s everything you need to know about the 27-year-old’s lengthy dating history.
Davidson had a fling with the Girl Code star in 2015. And when the news broke that he was dating Grande, Aquilino kept things cryptic. She posted a screenshot from a friend in a since-deleted Instagram Story which said, “I know I’m the 9 billionth person to text you today about this, but… I can’t.”
The two still seem to be friends: They are often spotted hanging out together, and Aquilino even co-starred in Davidson’s 2020 film, The King of Staten Island.
Before Grande, there was comedian Larry David’s daughter, writer and actress Cazzie David. The two young comedians began their relationship in 2016 and were on-and-off for two-and-a-half years until May 2018.
David reacted with humor to the news of Davidson’s next relationship with Grande, saying on Instagram, “Been in Africa, what’d I miss?” In an interview with the Los Angeles Times, she later reveal that she was the one to originally ask for a break from the relationship, but when she decided she wanted to give things another try, Davidson told her he was “the happiest he had ever been.” A few days later, he broke up with her for good and had covered his tattoos inspired by her.
After the breakup, David became good friends with Grande’s ex-boyfriend, the late rapper Mac Miller, and showed up to the 2019 Grammys with his parents following his untimely passing.
On May 18, 2018, Bossip broke the news that Grande and Pete Davidson were dating. On June 9, 2018, Davidson proposed to her at Robert Pattison’s birthday party. By October 2018, the two called off their engagement.
“I pretty much knew it was over after that,” Davidson told Charlamagne tha God of their relationship after Mac Miller’s death on Sept. 7, 2018. “All I do know is that she really loved the s*** out of him and she wasn’t putting on a show or anything. That was f***ed up and prayers to his family and all of his friends, still.”
Davidson was spotted with Beckinsale, who is 20 years older than him, at the 2019 Golden Globes in January 2019. Their fling ended in April 2019. After the breakup, he said she was “one of the funniest people I’ve ever met.”
The Once Upon a Time in Hollywood star and Davidson dated from August 2019 to October 2019. They allegedly remain friends.
Davidson began dating Cindy Crawford’s 18-year-old daughter in November 2019. The pair dated for three months until January 2020. Some outlets speculated that Davidson, who has been open about living with borderline personality disorder, may have sought out rehabilitation during their time together.
Davidson later suggested he was going through heavy stuff while he dated Gerber and that their age difference wasn’t ideal.
“We were dating for a few months and she’s very young and I’m f***ing going through a lot,” Davidson told Charlamagne tha God. “She should be having fun and s***. She shouldn’t have to worry about some dude who has issues and s*** … It just wasn’t like the right place or the right time.”
On Mar. 22, 2021, Page Six revealed that Davidson had begun dating the 25-year-old Bridgerton actress. Davidson was spotted visiting Manchester where Dynevor is staying with her mother, the Coronation Street actress Sally Dynevor.
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