Carly Aquilino
Davidson briefly dated the Girl Code star in 2015—and he remains close friends with the fellow comedian. They were spotted hanging out after one of his comedy shows in February 2019 and Aquilino co-starred in his 2020 film, The King of Staten Island.
Cazzie David
David, the daughter of Curb Your Enthusiasm's Larry David, revealed a lot about her two-and-a-half year romance with Davidson in her 2020 book of essays, No One Asked For This. The couple first began dating in 2016, with David writing that they were "kindred spirits." But she admitted Davidson's mental health struggles had taken a toll on her.
"Previously, self-harm and suicide threats had come about from trivial circumstances, incidents that would go from 0 to 100, which were so momentarily urgent, like the last minute of an escape room before the time goes off, except I'm the only one in the room and all the clues are tricks," she recalled. "Once he was back in a good headspace, I wouldn't be able to bring myself to do it either; I was too mentally exhausted to do anything besides emotionally recover from the chaos of the week before."
After she ended their relationship while on a family trip, David attempted to reconcile with Davidson in a moment of weakness. But she was shocked when he later sent her a text message to reveal he had moved on.
Two days later, she opened Instagram to see her ex had "uploaded of himself with his hand covering his face to show off his new finger tattoos," she wrote. "My name, which had been written in cursive across his ring finger, was now covered over with black ink."
Ariana Grande
Weeks after Davidson and David's breakup—and not long after Grande's split from rapper Mac Miller—E! News confirmed that the actor and the pop star were casually dating.
But things went from 0 to 100 when with the couple—who met when she hosted SNL two years earlier—went Instagram official and got matching tattoos by their one-month anniversary. And by June of 2018, the pair were engaged and living together in a $16 million NYC loft alongside their adopted pet pig.
"They're just two people who found love quickly and make each other happy all the time," a source shared with People at the time. "They both started talking about it this past weekend. It's nothing they've been hiding."
Their whirlwind romance came to an end in October 2018, with the news of the split coming one month after Miller was found dead of an apparent overdose at age 26.
Davidson processed the breakup by using it in his standup comedy sets, while Grande channeled her feelings into a hit song and album, thank u next.
Kate Beckinsale
Three months after his split from Grande, the King of Staten Island star kicked off a "casual" romance with Beckinsale, according to a source.
"They spend most of their time on opposite coasts so it's a casual thing," a source told E! News the time. "But they are going to keep talking and having fun together."
During the course of their brief courtship, Davidson and the Underworld star attended parties, hockey games and even enjoyed dinner with Beckinsale's parents. But the romance fizzled out after three months, a source explaining that it has simply "ran its course," adding, "They still talk and are very friendly."
Margaret Qualley
The comedian and the Once Upon a Time in Hollywood star first sparked dating rumors in August 2019 when they were spotted together in Venice for the premiere of Qualley's film, Seberg. The two were then spotted on a romantic stroll and walking hand-in-hand as they explored the city.
While neither Davidson nor Qualley ever confirmed their romance, her mom Andie MacDowell ended up spilling the beans in an interview. "She has a beautiful relationship with him but I don't want to step on her relationship too much," MacDowell told People. "They have a nice relationship."
But the couple called it quits after two months, with a source telling Us Weekly at the time, "They remain friends."
Kaia Gerber
Davidson and Gerber, the model daughter of Cindy Crawford and Rande Gerber, began dating in October 2019, quickly becoming inseparable as they were spotted out and about in NYC.
But weeks into their romance, the then 18-year-old's concerned parents intervened, a source telling E! News that they were trying to "guide [Kaia] and to help Pete through a difficult time."
By January 2020, another insider close to Davidson told E! his relationship with Gerber was "cooling off" as he prioritized his mental health by seeking treatment. A third source said "there was no bad blood" between the pair.
Phoebe Dynevor
Let's hope Lady Whistledown wasn't upset she was scooped by the paparazzi when Davidson was spotted with the Bridgerton breakout star in April of this year. The two stars were snapped in England getting cozy outside of a grocery store and appeared to take a playful stroll together in a field. At one point, they were photographed with their arms around each other. The outing came one month after reports emerged that the unexpected pair were spending time together.
While they never publicly confirmed their romance, the couple did offer clues. They were spotted wearing matching silver monogrammed necklaces bearing their shared initials, "PD," and Davidson said the actress was his "celebrity crush" in a Zoom Q&A with college students.
A source close to Davidson told E! News that he is "very into Phoebe" and has been flying back and forth from NYC to the U.K. "any chance he gets." The insider explained, "He doesn't mind, because he's very excited about spending time with her. She's getting to know him and loving this attention."
However, by August, they had split. "The long distance made it very difficult," a source shared with E! News. "They had fun, but it wasn't sustainable being so far apart. It was great while it lasted, but they both agreed it was best to move on."