Why Pete Davidson Worries About Being Known as a "Loser" in Love

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 in 2018, 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 a photo 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."

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 casual to serious AF when 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. 

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 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. 

Three months after his split from Grande, the King of Staten Island star kicked off a breezy romance with Beckinsale.

"They spend most of their time on opposite coasts so it's a casual thing," a source told E! News at 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 had simply "ran its course," adding, "They still talk and are very friendly."

The comedian and the Once Upon a Time in Hollywood star first sparked dating rumors in August 2019 when they were seen together in Venice for the premiere of Qualley's film, Seberg. The two were then spotted on a romantic stroll, 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.

Davidson and Gerber—the 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.

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 2021. The two were snapped in England getting cozy outside of a grocery store and appeared to take a playful stroll together in a field. 

Throughout their months-long romance, the couple offered several clues about their coupling. 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. 

"It just goes back to being naïve—I didn't think anyone would care," she later told Elle of their experience. "I was just being a young woman and dating and somehow that provokes a conversation. There were lots of hard lessons I had to learn through basically just having a personal life."

A source close to Davidson told E! News that he was "very into Phoebe" and had been flying back and forth from NYC to the U.K. The insider explained, "He doesn't mind, because he's very excited about spending time with her."

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."

Live from Las Vegas...the Outer Banks lead, who previously dated costar Chase Stokes, was first linked to Pete in September 2023, when she flew to Sin City for the comedian's Pete Davidson Live standup show at the Chelsea, People reported. The pair called it quits less than a year later.

And while neither has shared exactly how their romance began, Davidson previously told Jon Bernthal on the Real Ones podcast, "These people that I've dated, I met them at work. I wasn't in anyone's DMs, no one was in mine."