You’ve seen the memes. Pete Davidson, a guy who often describes himself as looking like he’s perpetually recovering from a mild flu, walking hand-in-hand with some of the most famous women on the planet. It's become a recurring internet phenomenon. Every few months, like clockwork, a new photo drops, and social media has a collective meltdown. How does he do it? Is it the BDE (Big Dick Energy) that Ariana Grande famously tweeted about? Or is it just that he’s actually, well, a nice guy?
Honestly, the obsession with Pete Davidson exes has reached a fever pitch that almost eclipses his actual career on Saturday Night Live or his stand-up specials. It’s a roster that feels like a curated VIP list for a Met Gala after-party. But if you look past the paparazzi shots and the TMZ headlines, there is a weirdly human story about a guy just trying to date in the most public, high-pressure environment imaginable.
The Whirlwind Years: From SNL to Ariana Grande
Before he was a household name for his dating life, Pete was just the "young kid" on SNL. His first major public relationship was with Carly Aquilino, the star of MTV’s Girl Code. They dated back in 2015. It was low-key. Normal. Then came Cazzie David, daughter of comedy legend Larry David. They were together for two and a half years, which is practically a lifetime in "Pete Years."
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Then, May 2018 happened.
The world shifted. Pete and Ariana Grande didn't just date; they detonated. Within weeks, they were engaged. They got matching tattoos. He bought a $16 million apartment for them. It was a manic, neon-colored fever dream that lasted exactly five months. When they split in October 2018—following the tragic death of Ariana's ex, Mac Miller—the internet didn't just move on. It became obsessed with Pete's "pull."
Why the Internet is Obsessed With His Roster
People love a mystery. And to many, Pete Davidson is a walking enigma. He’s been open about his struggles with Borderline Personality Disorder (BPD) and Crohn’s disease. He’s tatted from his neck to his toes. He once lived in his mom’s basement in Staten Island.
Yet, the list of Pete Davidson exes kept growing:
- Kate Beckinsale: The 20-year age gap make-out session at a Rangers game that launched a thousand memes.
- Margaret Qualley: A brief, chic romance that took them to the Venice Film Festival.
- Kaia Gerber: Cindy Crawford’s daughter. This one ended when Pete checked into rehab, showing that even amidst the glitz, his real-life struggles were always present.
- Phoebe Dynevor: The Bridgerton star. They were the "it" couple of the 2021 Wimbledon season.
The Kim Kardashian Era
If Ariana was the explosion, Kim Kardashian was the tectonic shift. When they kissed during an Aladdin sketch on SNL in October 2021, nobody thought it was real. But then came the Staten Island pizza dates. Then the Met Gala, where Pete stood back while Kim navigated the stairs in Marilyn Monroe’s dress.
It lasted nine months. It involved a very public, very strange feud with Kanye West. It was the moment Pete Davidson stopped being "that guy from SNL" and became a global protagonist in the Kardashian cinematic universe.
The Reality of "The Pete Davidson Effect"
Emily Ratajkowski (who also had a brief fling with him in late 2022) probably explained it best. She basically said that men are the only ones confused by his appeal. To women, it's simple: He's tall. He's funny. He's vulnerable. He’s "comfortably charming."
In a 2025 interview, Pete admitted that the attention on his dating life felt like a "living hell." He hates that people think he's just "the guy who dates people." He told Complex that in 12 years, he’s dated maybe 10 people. In the real world? That’s just a normal 20-something trying to find a connection. In Hollywood? It's a "roster."
Where is he now?
As of early 2026, the narrative has shifted again. Pete has been in a serious relationship with model Elsie Hewitt since March 2025. They even announced they are expecting their first child together. It feels like the "chaos" era might finally be settling into something more permanent.
Lessons From the Pete Davidson Timeline
What can we actually learn from all this? First, stop over-analyzing. Sometimes a guy is just fun to be around. Second, vulnerability is a magnet. Pete doesn't hide his mess; he talks about it in his sets.
If you're following the Pete Davidson exes saga for the drama, you're missing the point. The "mystery" isn't about what he "has" on these women. It’s about the fact that in a world of curated, plastic perfection, a guy who is honest about being a bit of a disaster is actually the most refreshing thing in the room.
How to Navigate Your Own Dating Life Like an Adult
- Be Upfront: Like Pete, don't hide your baggage. It’s going to come out anyway.
- Focus on Humor: You don't need a $16 million condo if you can make someone genuinely belly-laugh.
- Respect the End: Most of Pete’s exes still speak relatively well of him. Avoid the "scortched earth" breakup.
- Ignore the Gallery: Whether it's 10 million followers or just your nosy aunt, people will always have opinions. Let them.
The best way to stay updated on Pete's journey isn't through gossip sites, but by watching his actual work. His latest stand-up and film projects often provide the context that the paparazzi photos leave out. Check out his 2024-2025 comedy specials for a more nuanced look at how he views his own fame and relationships.