Pete Davidson's Revolving Door: A Decade of Whirlwind Romances

When you think of Pete Davidson’s dating life, the word“stability”probably doesn’t come to mind. The comedian has spent the last decade cycling through relationships at a pace that would make anyone’s head spin—from brief flings to whirlwind engagements, each romance seemingly more high-profile than the last.

Davidson’s journey through celebrity dating began in earnest with Cazzie David, the Eighty-Sixed creator, whom he dated on and off from May 2016 until early 2018. Things ramped up considerably when he got engaged to Ariana Grande just weeks after they started dating in 2018, only to call it quits that same October. That pattern—moving fast, burning bright, fizzling out—would become the defining rhythm of his romantic life.

What’s striking isn’t just the frequency of these relationships, but the caliber of people involved. After Grande came Kate Beckinsale, Margaret Qualley, and model Kaia Gerber, followed by Bridgerton star Phoebe Dynevor. Then came the heavyweight matchup that actually grabbed mainstream attention: his nine-month stint with Kim Kardashian, which began in October 2021 after they worked together on Saturday Night Live. A source told Us Weekly at the time that Kardashian was“falling for”Davidson, noting that“he makes her laugh”and“feel good.”But even that high-profile pairing fizzled by August 2022.

The years that followed saw Davidson paired with Emily Ratajkowski, Bodies Bodies Bodies costar Chase Sui Wonders, Outer Banks actress Madelyn Cline, and most recently Elsie Hewitt. That last relationship appeared to be heading somewhere—they made their red carpet debut in May 2025 and were even expecting a baby together by July. Yet by December 2025, the couple had already split.

What makes Davidson’s pattern fascinating isn’t judgment about commitment—it’s the consistency of the pattern itself. These aren’t relationships that develop slowly or privately before becoming public. They’re intense, visible, and brief. Whether that speaks to incompatibility, changing circumstances, or simply the friction of dating in the public eye remains an open question. But one thing’s clear: if Pete Davidson ever does find something that sticks, the world will definitely be watching.