Looking Back at Pete Davidson's Stacked Dating History

Saturday Night Live star Pete Davidson has romanced Ariana Grande, Kaia Gerber and Bridgerton star Phoebe Dynevor. Now, he's causing a stir thanks to his outings with Kim Kardashian.

By Tierney Bricker Nov 06, 2021 7:00 AMTags
Watch: Kate Beckinsale Subtly Shows Support for Ex Pete Davidson

Women really do love a man that can make them laugh.

Since making his debut on Saturday Night Live in 2014, Pete Davidson has unexpectedly become one of the most eligible bachelors in Hollywood. So much so, in fact, that the 27-year-old comedian inspired the creation of the term "BDE." To refresh your memory, it stands for "Big D--k Energy" and was crafted at the height of his romance with Ariana Grande in 2018.

"Pete davidson is 6'3 with dark circles, exudes big d--k energy, looks evil but apparently is an angel, and loves his girl publicly the only thing wrong w him is that he's a scorpio but anyway," Twitter user @babyvietcong wrote. "id married him within a month too."

That BDE has seemingly attracted a bevy of women, including Kate BeckinsaleKaia Gerber and his "celebrity crush" Phoebe Dynevor. Now, he's causing a stir thanks to his frequent outings with Kim Kardashian. The duo were first spotted together at Knott's Scary Farm in Buena Park, Calif Oct. 29. Four days later, they enjoyed dinner at Campania in New York's Staten Island. And, the following day, they were seen out at again Zero Bond restaurant in NYC.

Kim Kardashian's SNL Debut After-Party

And while a source told E! that "Kim isn't looking to date anyone right now," she is "having a lot of fun. There is no pressure between them." After all, she likes that "Pete a very chill and casual guy," added the insider. "Whatever is going on between them is exciting to her."

Well we all wait and see what's next, let's take a look back at the SNL star's high-profile romances over the years, from his whirlwind engagement to Grande to his courtship with the Lady Bridgerton herself...

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."

This story was originally published on Saturday, May 8, 2021 at 3 a.m. PT.