Yes, Pete Davidson's Dating History Was Stacked Well Before He Was Linked to Madelyn Cline

Outer Banks star Madelyn Cline is just the latest celeb to become entranced with Pete Davidson's big dating energy. And we're diving deep into his rich dating history.

By Sarah Grossbart Oct 01, 2023 12:00 PMTags
Watch: Kim Kardashian Shares Regret Over Pete Davidson Romance

At this point, perhaps we should be asking who wouldn't want to date Pete Davidson. Because to hear his previous paramours tell it, the Saturday Night Live alum has a list of alluring traits as big as his...6-foot-3 stature.

"He's got the height," model Emily Ratajkowski shared on on Late Night With Seth Meyers in 2021, roughly a year before her weeks-long entanglement with the comedian. "Obviously women find him very attractive."

So, no, the mom to Sylvester, 2, doesn't get the confusion. "Guys are like, 'Wow. What's that guy got?,'" she explained. "And I'm like, I mean, he seems super charming. He's vulnerable. He's lovely. His fingernail polish is awesome. He looks good!"

And, of course, there's all the talk of his BDE—one-time fiancée Ariana Grande initiating chatter about his member before saying thank u, next to their brief engagement. 

Though Davidson later insisted his manhood is "very normal-sized," the talk was enough to catch Kim Kardashian's attention. 

Kim Kardashian and Pete Davidson: Romance Rewind

"I did SNL and then when we kissed in-scene, it was just a vibe," she shared on The Kardashians. "I was like 'Oh s--t...maybe I just need to try something different.'"

When she reached out to a producer to get his number, she continued, "I wasn't even thinking like 'Oh my god I'm gonna be in a relationship with him,'" she continued. "I was just thinking...I heard about this BDE. I need to get out there...I was just basically DTF."


Instead Davidson kept her entertained for nine straight months. "He just makes her laugh," sister Khloe Kardashian explained in 2022 Good Morning America interview, "and she laughs all the time."

Now Outer Banks actress Madelyn Cline is looking for a little levity, diving into a romance with the Bupkis lead after ending her relationship with costar Chase Stokes

While the King of Staten Island has yet to speak out about his new queen, she's not the first to receive his royal treatment. "In 10 years, I've dated 12 people," the 29-year-old explained on a March episode of the Real Ones With Jon Berthnal podcast. "I don't think that's that crazy, but to some people, that's very interesting."

And we're some people. Join us in taking a look back at all of the ladies who have been entranced by Davidson's big dating energy. 

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."