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Pete Davidson is the human equivalent of a Rorschach test for the internet. Some people look at him and see a talented comedian who used Saturday Night Live as a springboard to movie stardom; others just see a guy with dark circles under his eyes who somehow manages to date every A-list woman in Hollywood. It’s a phenomenon. Seriously. If you’ve spent any time on social media over the last five years, you’ve probably asked yourself: who did Pete Davidson date, and more importantly, how?
The fascination isn't just about the names. It’s about the contrast. We’re talking about a guy who used to live in his mom’s basement in Staten Island suddenly appearing on the arm of pop royalty and billionaire entrepreneurs.
The Ariana Grande Era: The Spark That Started the Fire
Before 2018, Pete was a "cool if you know him" cast member on SNL. Then came Ariana Grande. This wasn't just a fling; it was a cultural reset. They met when she hosted the show, but things didn't kick off until they both ended long-term relationships—Pete with Cazzie David and Ariana with the late Mac Miller.
They moved fast. Like, light-speed fast.
Within weeks, they were engaged. Pete got her initials tattooed on his hand. Ariana released a song literally titled "pete davidson." It gave us the term "Big Dick Energy," or BDE, coined by fans to explain Pete’s inexplicable pull. But the bubble burst. Following the tragic death of Mac Miller and the overwhelming pressure of a public-facing whirlwind romance, the engagement ended in October 2018. It left Pete as a household name, though perhaps not for the reasons he originally intended.
The Cazzie David Complication
You can’t talk about Ariana without mentioning Cazzie David. The daughter of Larry David, Cazzie was Pete’s girlfriend for two and a half years. Her book of essays, No One Asked for This, paints a pretty raw picture of their breakup. She describes Pete breaking up with her via text just days before his relationship with Ariana went global. It’s a reminder that behind the "BDE" memes, there are real people and occasionally messy endings.
Why Pete Davidson’s Dating History Defies Logic
If you look at the list of women Pete has been linked to, there’s no "type." He’s dated supermodels, actresses twice his age, and reality TV titans.
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He’s the rebound king.
Or maybe he’s just a nice guy? Sources close to his exes often mention how "charming" and "vulnerable" he is. In a world of curated Instagram boyfriends, Pete is messy, honest about his mental health struggles (he’s been open about his Borderline Personality Disorder diagnosis), and doesn't take himself too seriously. That’s high-value currency in Hollywood.
The Ageless Charm of Kate Beckinsale
In early 2019, Pete shocked everyone again by dating Kate Beckinsale. She’s an iconic British actress, 20 years his senior, and seemingly from a different world. They were spotted making out at a Rangers game, looking like they didn't have a care in the world. It lasted about four months. When asked about the age gap, Pete famously joked on Weekend Update that people should be asking the same questions about older men dating younger women. Fair point, Pete.
Entering the High-Fashion World
After Kate, the caliber of fame just kept climbing. He dated Margaret Qualley (of Once Upon a Time in Hollywood fame) and then moved on to Kaia Gerber.
Kaia was only 18 at the time, and Pete was 26. This one drew a lot of heat. Her parents, Cindy Crawford and Rande Gerber, were reportedly concerned. Pete eventually addressed the split in a sit-down with Charlamagne tha God, admitting that he was going through a lot of personal "mental shifts" and it wasn't the right time for a serious relationship with someone so young.
- Margaret Qualley: A brief summer romance in Venice.
- Kaia Gerber: A few months of NYC walks and intense paparazzi scrutiny.
- Phoebe Dynevor: The Bridgerton star. They did the long-distance thing between NYC and the UK during the height of the show's popularity. They even wore matching "PD" necklaces.
The Kim Kardashian Chapter: Breaking the Internet (Again)
If Ariana Grande put Pete on the map, Kim Kardashian cemented him as a permanent fixture.
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They met when Kim hosted SNL in October 2021. They shared a kiss during an Aladdin-themed sketch. A few weeks later, they were holding hands on a rollercoaster at Knott's Scary Farm. The world lost its mind. This was Kim’s first major relationship after filing for divorce from Kanye West.
It was a strange, fascinating nine months. Pete got several tattoos dedicated to Kim, including one that said "My girl is a lawyer" and a literal branding of her name on his chest. Think about that for a second. A brand. He hung out with her kids. He went to the Met Gala in a classic suit while she wore Marilyn Monroe’s dress.
But the "Kanye of it all" was heavy. The constant social media attacks from Kim’s ex-husband put a massive strain on the relationship. By August 2022, they called it quits, citing their demanding schedules and the difficulty of long distance while Pete was filming in Australia.
Who Did Pete Davidson Date Recently?
The post-Kim era hasn't been quiet. Pete has a way of moving on that makes your head spin.
- Emily Ratajkowski: A brief "vibe" that lasted a few weeks in late 2022. It was the ultimate "it girl" and "it boy" pairing.
- Chase Sui Wonders: His co-star from the movie Bodies Bodies Bodies. This felt more grounded. They were together for nearly a year, traveled together, and seemed genuinely happy until they split in mid-2023.
- Madelyn Cline: The Outer Banks star. They were linked throughout late 2023 and early 2024.
The "Pete Effect" Explained by Experts
Why do these high-profile women flock to him? It’s not just a meme. Dr. Jennifer Rhodes, a psychologist who has spoken on celebrity relationship dynamics, suggests that Pete offers "emotional safety." In a high-pressure environment like Hollywood, a guy who is funny, self-deprecating, and doesn't try to outshine his partner is incredibly attractive.
He’s also a "safe" rebellion. For someone like Kim Kardashian, who had spent a decade in a highly controlled, high-stress marriage, Pete was a breath of fresh Staten Island air. He’s the guy who will take you to get pizza in his pajamas.
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The Realities of Public Breakups
It’s not all fun and games. Every time Pete enters a new relationship, his past is excavated. The internet treats his dating life like a sport, but it takes a toll. Pete has deleted his Instagram multiple times due to harassment. He’s checked into wellness facilities to manage his BPD and PTSD.
When you ask who did Pete Davidson date, you’re looking at a timeline of a young man’s life played out under a microscope. Some of these women were "the one" for a moment, and others were likely just two people enjoying a night out who got caught by a long lens.
Lessons from the Davidson Dating Playbook
What can regular people learn from Pete? Honestly, a lot.
- Authenticity Wins: Pete doesn't pretend to be a polished Prince Charming. He’s open about his flaws, and that creates instant intimacy.
- Humor is a Superpower: You don’t need a six-pack if you can make someone laugh until they cry.
- Support Your Partner: In every relationship, Pete seems to be the "Instagram boyfriend," the cheerleader, and the one willing to step out of the spotlight to let his partner shine.
Moving Forward
As of 2026, Pete seems to be focusing more on his sobriety and his acting career. He’s moved back to the suburbs, away from the chaos of the city. He’s still a frequent topic of conversation, but the frantic pace of his dating life seems to have leveled out—at least for now.
If you're trying to keep track, don't get too attached to any one headline. Pete Davidson’s life moves fast. One day he’s at a Knicks game with a new co-star, and the next he’s disappeared from the public eye to work on a new stand-up special.
If you want to stay updated on Pete's latest moves without the tabloid fluff, keep an eye on his project announcements rather than the paparazzi shots. The best way to understand Pete isn't through who he's holding hands with, but through his comedy. That’s where he tells the truth.
To dig deeper into the "Pete Effect," look into the psychology of "rebound relationships" or the history of SNL cast members who became tabloid fixtures. You'll find that Pete is part of a long tradition of "funny guys" who captured the heart of the zeitgeist, even if he did it with a bit more Staten Island flair than the rest. Check out his 2023 special Turbo Fonzarelli for his own take on his reputation; it provides a much-needed perspective that the headlines usually miss. Take a look at his filmography, specifically The King of Staten Island, to see how much of his real-life dating trauma and family history he pours into his work.
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