The SNL star was most recently spotted with model Kaia Gerber, though a source says the two are "just friends"

By Kate Hogan
November 15, 2019 04:00 PM

Fresh off his split from actress Margaret Qualley, SNL star Pete Davidson has been spotted spending time with model Kaia Gerber.

The actor, 25, and the supermodel, 18, were spotted in New York City together in late October, enjoying a meal at the popular brunch restaurant, Sadelle’s. A source told Page Six the two are “just friends,” however, he was also photographed leaving her apartment that day.

Later in the week, they both attended a New York Knicks basketball game, though they sat separately, with Gerber joining her dad Rande. However, the two looked back on one week later, driving around Malibu together and later, grabbing dinner in L.A. (She even wore a “P” necklace while at an event with her mother, Cindy Crawford, and her grandmother.) Most recently, they were photographed holding hands on a trip to upstate New York.

If the two are dating, it makes Gerber the latest in a list of high-profile pairings for the funnyman. Here, a look back at Davidson’s dating history.

Margaret Qualley

Davidson and the up-and-coming actress, 25, were first spotted together in September after touching down at the Marco Polo airport in Venice, where a source told PEOPLE they looked “very happy” together.

“They were very smiley and flirty. Some fans approached them and they happily signed autographs,” the source shared. “They left the airport together for the same hotel.”

Pete Davidson and Margaret Qualley in Venice on Sept. 2, 2019
| Credit:

A day later, the comedian and daughter of Andie MacDowell were photographed at the premiere of Margaret’s film Seberg at the Venice Film Festival.

They kept their public outings going on Labor Day, where they were snapped taking a stroll through the streets of Venice walking hand-in-hand together.

After a few months of dating, the two quietly split in the early fall.

Kate Beckinsale

The actress, 46, and Davidson had quite the public romance earlier in the year, dating for four months before splitting in April.

The two were first spotted together for most of the night at Netflix’s Golden Globes afterparty in January. In early February, Beckinsale supported Davidson at his stand-up comedy show in Los Angeles. The two left the venue hand-in-hand.

That same month, they were spotted enjoying a hockey game at Madison Square Garden in New York City, where they packed on the PDA for the cameras.

“She’s very happy with Pete,” a source close to the actress told PEOPLE at the time. “They have really similar senses of humor and she’s always laughing with him.”

Kate Beckinsale and Pete Davidson at a New York Rangers hockey game on March 3, 2019
| Credit: JD Images/REX/Shutterstock

During the end of Davidson’s appearance on Weekend Update, Colin Jost asked if his costar had any new life developments, “like a new girlfriend.” Davidson was initially reluctant but soon opened up about Beckinsale.

“Apparently people have a crazy fascination with our age difference,” replied Davidson. “But it doesn’t really bother us. But then again, I’m new to this.”

By the end of April, though, a source told PEOPLE they “are over,” but that things between them ended amicably.

“It was the long distance,” said the source. “They’re still friendly, but it just didn’t work out.”

A second source added, “They had been trying to make it work up until very recently, but it’s over now.”

Ariana Grande

Davidson’s star shot up in May 2018, when he was first linked to singer Grande, 26. They were first spotted together backstage at the Billboard Music Awards, where Grande performed.

“After Ariana’s performance, they were backstage and he had his arm around her,” an onlooker told PEOPLE. “They seemed very lovey-dovey. He was hanging out with her and her friends with his arm around her. She seemed quite smitten.”

They went Instagram-official weeks later, and from there kept their romance quite public, stepping out for dates in N.Y.C. and even getting some couples ink: Davidson got a neck tattoo that seemingly referenced the “No Tears Left to Cry” singer’s Dangerous Woman album cover, plus her initials on his hand.

Pete Davidson and Ariana Grande at the MTV Video Music Awards in N.Y.C. on Aug. 20, 2018
| Credit: Evan Agostini/Invision/AP/REX/Shutterstock

After a few weeks of dating, an insider close to the couple confirmed the duo were officially engaged. “It’s a recent engagement. They’re just two people who found love quickly and make each other happy all the time,” the source told PEOPLE.

After a whirlwind summer, the two split in October 2018.

“It was way too much too soon,” a Grande source told PEOPLE. “It’s not shocking to anyone.”

Sources close to the couple told TMZ that the decision to split was a mutual choice, as both of the stars felt the timing wasn’t right.

Cazzie David

The SNL star kept things lower-key when he dated David, 25, the daughter of actor Larry David. The pair first went public in 2016, splitting in early 2018.

“I just love her very, very much,” Davidson told PEOPLE in 2016.

Announcing he was sober in 2017, he credited David and his friends for sticking with him along the way.

“It wasn’t easy, but I got a great girl, great friends and I consider myself a lucky man. I’ll always be here for you guys, I promise,” he wrote on Instagram. “Remember to never give up hope because sometimes that’s all we got. We are a family and I appreciate all your love and support. It’s nice to be back in action.”

Pete Davidson and Cazzie David at the Curb Your Enthusiasm premiere afterparty in N.Y.C. on Sept. 27, 2017
| Credit: Jamie McCarthy/Getty

He also dedicated an Instagram post hours later to Cazzie.

“Couldn’t pick one so I went with two,” he captioned a side-by-side picture of the couple. “Luckiest guy in the world #babygirl.”In May 2018, he confirmed the pair’s break-up in an interview with Complex.

“We’re not together anymore,” he said. “Very talented girl, she’ll be great and she’ll be fine. Yeah, I think she’ll be okay.”

Carly Aquilino

Davidson and Aquilino dated quietly in 2015. Though the two were never very public about their romance, the stand-up comedian and star of MTV’s show Girl Code appeared to share her reaction to her former boyfriend’s engagement to Ariana Grande on her Instagram story when the news broke last year, posting a screenshot of a text conversation with a friend.

Carly Aquilino at the 2016 MTV Video Music Awards in N.Y.C.
| Credit: Jamie McCarthy/Getty Images

“I know I’m the 9 billionth person to text you today about this, but… I can’t,” the friend wrote to her.

Aquilino’s response? “HAHHAHAHAAH.”

The comedian, 27, captioned the post, “My day in a text message.”