There are very few celebrities whose love lives generate as much consistent headlines as Pete Davidson. The comedian, actor, and former Saturday Night Live star has built a romantic resume that reads like a Hollywood guest list — supermodels, pop icons, reality TV royalty, and acclaimed actresses. And somehow, every single relationship ends up fascinating the internet in a completely different way.
So how did a guy from Staten Island become one of the most talked-about daters in pop culture? Let’s go through every relationship, in order, and find out.
Cazzie David (2016–2018)
Before the A-list era began, Pete Davidson dated writer and actress Cazzie David — daughter of Seinfeld creator Larry David — for about two years. It was a relatively low-key relationship by Davidson standards, though the breakup was anything but. Just days before confirming his relationship with Ariana Grande, Davidson announced his split from Cazzie David — a detail that made the next chapter feel even more chaotic.
Ariana Grande (May–October 2018)
This is the one that made the internet stop scrolling. Davidson and Grande were first spotted hanging out in May 2018 at a Saturday Night Live after-party. In true whirlwind fashion, he reportedly introduced Ariana to his mum days before confirming their engagement — just four weeks after they started dating. Two sets of matching tattoos and one very public emotional rollercoaster later, the flash-in-the-pan partnership was over by October 2018.
The engagement, the tattoos, the breakup — it was five months of tabloid content compressed into what felt like five weeks. Grande later channeled the relationship into her Thank U, Next era. Davidson channeled it into stand-up material. The internet turned it into a permanent cultural moment.
Kate Beckinsale (January–April 2019)
Shortly after the Grande split, Davidson was spotted getting cozy with actress Kate Beckinsale — a pairing that genuinely confused and delighted everyone in equal measure. The two were photographed together at a Golden Globes afterparty and were briefly an item through early 2019 before quietly parting ways.
Margaret Qualley (August–October 2019)
Next came actress Margaret Qualley, daughter of Andie MacDowell. The two were seen together at the 2019 Venice Film Festival, but the relationship lasted only a few months before ending.
Kaia Gerber (October 2019–January 2020)
Davidson began dating model Kaia Gerber — daughter of supermodel Cindy Crawford and businessman Rande Gerber — in late 2019. Their relationship ended after just a few months. Davidson later reflected warmly on the split, noting: “It just wasn’t the right place or the right time at all,” and praised her parents as “really helpful and stuff.”
Phoebe Dynevor (March–August 2021)
Fresh off Bridgerton‘s explosive debut on Netflix, Phoebe Dynevor became the next name in the Davidson dating timeline. Davidson was spotted in Manchester, England, and the pair even enjoyed a very public courtside date at Wimbledon. The long-distance relationship, however, didn’t survive the conflicting time zones, ending after just five months.
Kim Kardashian (October 2021–August 2022)
If the Ariana Grande chapter was a five-month tabloid story, the Kim Kardashian era was a full season of television. It all started with some confusing pictures at Knott’s Scary Farm, then evolved into a full-blown love affair that became his second-longest relationship ever.
The two went public after Kardashian’s SNL hosting appearance in October 2021 — they shared an on-screen kiss during a sketch and the rest, as they say, is gossip history. They dated for roughly nine months before splitting in August 2022, just as Kardashian’s divorce from Kanye West was being finalized. The relationship was scrutinized from every angle, but by all accounts it was real, and it put Davidson in a level of the spotlight he’d never quite experienced before.
Emily Ratajkowski (November 2022)
The model and actress was linked to Davidson soon after his split with Kim Kardashian, with rumors flying after the two were spotted at a Knicks game together in November 2022. Ratajkowski later addressed the public intrigue around the pairing, saying she appreciated that Davidson was simply respectful and easy to spend time with. The relationship appeared brief and was never officially confirmed.
Chase Sui Wonders (December 2022–August 2023)
Chase Sui Wonders and Pete Davidson were first linked together when they appeared alongside each other in the 2022 horror hit Bodies Bodies Bodies. The couple later played romantic partners again in Davidson’s Peacock series Bupkis. Their real-life romance lasted roughly eight months before an amicable split.
Madelyn Cline (Late 2023–July 2024)
One month after his split from Chase Sui Wonders, Davidson was reportedly dating Outer Banks star Madelyn Cline. The two were seen on low-key dates together, but by July 2024 they called it quits in what was described as an “amicable” breakup.
Maria Georgas (Brief, 2024)
The Bachelor‘s Maria Georgas and Davidson may have been an item briefly in 2024 after his breakup with Madelyn Cline. Their romance reportedly lasted only a couple of months.
Mohit Swami is the Head of Content at GYANTV, overseeing content strategy, editorial planning, and quality control across the platform. With experience in managing digital content workflows, he ensures that every article aligns with accuracy standards, audience relevance, and ethical publishing practices. His work focuses on building trustworthy, engaging, and reader-first content in health, lifestyle, and trending news categories.