The biggest celebrity news of the long Thanksgiving weekend was the apparent confirmation of the rumor that comedian Pete Davidson is dating Kaia Gerber, Cindy Crawford’s 18-year-old daughter. They’ve been spotted kissing in Miami, holding hands at a grocery store in New York, and getting sushi in Malibu. Somehow, against all odds, Pete Davidson has managed to seduce one of the world’s most symmetrical women yet again.
For Davidson’s critics, who are legion, the hookup is baffling, even infuriating. Kaia Gerber looks exactly like her mother, the most famous supermodel of all time. Meanwhile, Davidson has said, accurately, “I look like I make vape juice in a bathtub.” It’s the kind of romantic mismatch that has bedeviled tabloid consumers for years now. And for a long time, I will confess, it bedeviled me too.
Davidson’s dating life first started inspiring tabloid news cycles when he dated Larry David’s daughter Cazzie, who once inspired a riff on the Cut headlined “I Wish I Were Larry David’s Cool Daughter.” I remember idly clicking through photos of those two, in which Davidson—as he would surely say about himself—looked a bit like he had wandered in from a Tampa parking lot or was playing a murderer on Law and Order: SVU. “That’s a guy,” I thought.
Then last year, when his brief engagement to Ariana Grande was the celebrity romance of the summer, I peeped the paparazzi shot of Davidson and Grande strolling down a city street during their summer of love. Grande is wearing an oversize yellow hoodie, thigh-high boots, and a miniature Louis Vuitton bag. With her waist-length glossy ponytail and doll-like features, she is unmistakably someone. So it’s striking to see her gazing up with total adoration at Davidson, a hood drooping over his eyes. They’re both sucking on lollipops, but Grande is licking hers flirtatiously—it looks like work, like a pose—while Davidson has his tucked casually in his cheek like he’s barely thinking about it. He looks cool, I suddenly realized, and maybe even cute, if you were into that sort of thing. He’s … kind of rangy.
He has since dated Andie MacDowell’s stunning actress daughter, Margaret Qualley. And somewhere in there, he apparently had a fling with Kate Beckinsale, too, suggesting a pleasingly catholic sexual appetite. (She’s 46.) I eyed the photo of the two of them sitting courtside at some sporting event, making out with such slobbery panache that it could only have been performed for the benefit of the cameras. And I thought: gross. But also: huh. And then came Kaia Gerber. (By the way, yes, Gerber is just 18. But Davidson himself just turned 26. Mathematically, it is creepier for me to write this post.)
Davidson is funny, obviously, but to my eye he also looks like he is having fun being a famous person. “It’s fuckin’ lit, Jimmy!” he exclaimed to Jimmy Fallon of his short-lived engagement last year. Lit, you say! Fun! Indeed, a key part of the Davidson charisma is that he seems to have a consistently great time cartoonishly telegraphing his love. He’s game to kiss for the kiss cam and to walk red carpets, and paparazzi photographers magically keep finding him and his girlfriends on the street. He projects a nicely calibrated awareness of how bizarre his life has become. He’s obviously pursuing fame, but he holds it lightly and claims to view it skeptically. (“It’s all bullshit,” he told GQ. “GQ wouldn’t hit me up if I didn’t recently get engaged to a super famous person.”) Last year, he said he was living with his mother. That combination of easy confidence and self-deprecating humor is romantic kryptonite to a certain kind of woman (me). Davidson is the guy you date in high school because he’s got an IDGAF stoner vibe, except he’s actually got a good job.
Yes, Davidson has unmistakable “BDE,” a term captured by Cut writer Allison P. Davis last year to try to explain the comedian’s spirited self-assurance. But he’s not just a schmoozy Don Juan. His father was a New York City firefighter who was killed on Sept. 11, 2001, and Davidson speaks openly about his ongoing grief. His angst seems relentlessly directed inward. He really likes his parents. He’s open and self-aware. He’s a large, goofy, confident man who loves being in love. Despite his hapless shtick, he’s got a real handle on his public image. Obviously his appeal is not so mysterious at this point if Cindy Crawford’s daughter is into it. But still, amid a sea of skeptics, it feels good to unburden myself: Pete Davidson, I finally get it.