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 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."

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 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

Kate Beckinsale

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."

Margaret Qualley

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.

Kaia Gerber

Davidson and Gerber—the daughter of Cindy Crawford and Rande Gerberbegan 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 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."

Kim Kardashian

For nearly a year, Davidson and The Kardashians star enjoyed quite the ride, going public with their romance during an October 2021 outing at Knott's Scary Farm just weeks after her SNL hosting gig

And while the mother of four showed the Aladdin to her Jasmine a whole new world—he joined her on a trip to Tahiti, on her family's Hulu reality series and even on the Met Gala red carpet—by August 2022, the two had come back down to earth

Despite maintaining "a lot of love and respect for each other," a source told E! News, NYC-based Davidson and L.A. resident Kardashian found that the long distance dynamic and their demanding schedules "made it really difficult to maintain a relationship." 

Emily Ratajkowski

Quizzed about the comic's energy after they paired up for a 2021 campaign shoot, the model raved during an appearance on Late Night With Seth Meyers, "I mean, he seems super charming. He's vulnerable. He's lovely. His fingernail polish is awesome. He looks good!" Plus, she summed up, he has a "super great relationship with his mom."

So when the mama's boy reached out last November following his split from Kardashian and her breakup with husband Sebastian Bear-McClard, she decided it would be fun to catch up. As a source told E! News at the time, "Emily thinks Pete is a lot of fun to hang out with and they have flirtatious chemistry right now."

Their love experiment continued for the next few weeks with the My Body author helping Davidson mark his 29th birthday. Still, an insider stressed that neither was looking to label their situation, calling it "a chill relationship." And by December she was heating up with designer Jack Greer

Chase Sui Wonders

Davidson got back in the game with his Bodies Bodies Bodies love interest, the pair spotted at a December 2022 New York Rangers game alongside costar Rachel Sennott before a January date night at Universal Studios Hollywood. 

The two "became fast friends on Bodies, and it was just clear that we could work together super well," she told Nylon in May. "He’s such a pro, and acting with him is my favorite thing." Which is why she signed up for round two, appearing on his semi-autobiographical Peacock series Bupkis as his on-again, off-again girlfriend.

Off-camera, she continued, "We talk about everything and we are very open with each other about everything, and it feels like what's happening in our relationship is very sacred." But by late August, they were no longer feeling quite so blessed, multiple outlets confirming the couple had split

Madelyn Cline

Live from Las Vegas...the Outer Banks lead, who previously dated costar Chase Stokes, was in Sin City Sept. 23 when the comedian performed his Pete Davidson Live standup show at the Chelsea, People reported. 

And while neither has shared 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."

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