Pete Davidson has no shortage of beautiful love interests.
On Wednesday, the 25-year-old comedian was spotted spending time with 18-year-old model Kaia Gerber -- the daughter of supermodel Cindy Crawford and Casamigos co-founder Rande Gerber -- in New York City, sparking rumors that the two may be dating. ET has reached out to their reps for comment.
On the heels of yet another possible high-profile romance for Davidson, let's take a look at his star-studded dating history.
2015: Carly Aquilino
Davidson briefly dated fellow comedian Carly Aquilino in 2015. The 27-year-old Girl Code star appeared to have a reaction to his engagement to Ariana Grande in June 2018 when she took to her Instagram Stories after the news broke, sharing a pointed text message exchange she had with a friend who wrote, "I know I'm the 9 billionth person to text you about this but... I can't." Aquilino responded "HAHHAHAHAAH," and wrote, "MY DAY IN A TEXT MESSAGE" over the screenshot before sharing it with her followers.
However, the two still appear to be on good terms. In February, E! News reported that they were spotted together after his show at the Paramount in Huntington, New York, and were in a picture together shared by photographer Marcus Russell Price to his Instagram Stories.
2016: Cazzie David
Davidson started dating Seinfeld co-creator Larry David's 25-year-old daughter, Cazzie David, in 2016. ET spoke with Davidson at the Natural Resources Defense Council's Stand Up for the Planet Benefit gala in Los Angeles in April 2017, where he gushed about his then-girlfriend.
"She's the most beautiful girl in the world, look how lucky I am," he told ET. "She's so smart, look how smart she is. She is a very, very wonderful lady."
Davidson also opened up about her role in his sobriety, noting, "I'm very lucky. She's very, very supportive."
However, the two split in 2018. Davidson broke the news during an interview with Complex's Open Late With Peter Rosenberg last May and had nothing but kind words for his ex. Davidson called David "a very talented girl," adding, "She'll do great, she'll be fine."
2018: Ariana Grande
Davidson and 26-year-old Grande were first linked in May 2018, when a source told ET that they were dating shortly after their respective splits -- Davidson from David and Grande from the late rapper Mac Miller. Their romance quickly escalated, and the two got engaged last June after just a few weeks of dating.
However, after a highly publicized romance, Davidson and Grande called it quits last October.
“Ariana made the final decision," a source told ET about their breakup at the time. "It was time to realize this wasn’t the right time for them and Pete is incredibly heartbroken. Pete is still so in love with her. He wanted his whole world to revolve around her but she was emotionally unavailable. He realizes she was at her limit with pressure from everyone and everything around her. There were days she just wanted to run away from the world just to get some peace and quiet and peace of mind. Pete had to give her that space out of love."
Although Grande has spoken kindly about Davidson after their split -- saying she was "thankful" to him in her hit song, "Thank U, Next," and referring to his ahem, "energy" -- in July, she admitted meeting Davidson was a "distraction" after breaking up with Miller in an interview with Vogue.
"My friends were like, 'Come! We're gonna have a fun summer,'" she recalled of moving out of Los Angeles and to New York last year. "And then I met Pete, and it was an amazing distraction. It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn't know him."
2019: Kate Beckinsale
Davidson moved on from Grande with yet another A-lister, 46-year-old actress Kate Beckinsale. The two were first linked together in January when an eyewitness told ET they were being "super flirty" at a Golden Globe Awards after-party, and later, they weren't shy about showing plenty of PDA.
Beckinsale acknowledged their romance in an interview with The New York Times in March.
"I've never been in this position before -- never dated anybody who comes with their own bag of mischief," she said. "It’s all quite shocking, and something to get used to."
"I think if you liked the person less, you would bow out of it," she continued. "If that were the main thrust of the relationship, there would be a problem. But it’s not."
But their surprising romance fizzled after four months. A source told ET in April that they were no longer dating, but still remained on friendly terms.
2019: Margaret Qualley
Us Weekly reported that Davidson was dating Once Upon a Time in Hollywood star Margaret Qualley in August. Shortly after, the Saturday Night Live star was spotted attending 25-year-old Qualley's Seberg movie premiere at the Venice Film Festival, and they were snapped holding hands while strolling through Venice, Italy.
However, it turned out to be another short-lived romance for Davidson. According to multiple outlets, he and Qualley -- the daughter of actress Andie MacDowell -- split earlier this month after two months of dating.
For more on Davidson and Qualley's relationship, watch the video below: