Pete Davidson has been on a roll in terms of romance since circa 2016, and it’s safe to say he holds one of the finest dating résumés in Hollywood—one that also seems to be ever-growing.
Whether it’s his so-called “BDE” or genuine charm that has landed him some of today’s most famous leading ladies, Davidson’s dating history has become a pop culture phenomenon in recent years.
Among the famous beautiful women he’s been romantically involved with are those who found him after going through very public divorces or breakups (Kim Kardashian and Emily Ratajkowski), and because of that, some have deemed Davidson Hollywood’s “recovery boyfriend.”
Ahead, look back at the former Saturday Night Live star’s extensive romantic history, from his first long-term relationship, with Cazzie David, to his whirlwind engagement to Ariana Grande.
Emily Ratajkowski (November 2022–Present)
Davidson’s current romance with Ratajkowski—one of the most unexpected relationships of 2022—was first confirmed by sources in November after the two were spotted holding hands in Brooklyn. The pair have since been captured on various outings around New York, including dates at Davidson’s Brooklyn residence and an NBA game at Manhattan’s Madison Square Garden.
“Pete makes Emily laugh and he loves how intelligent she is,” an Us Weekly insider told the outlet. “Emily thinks Pete is a lot of fun to hang out with,” another source said, this one per E! News, adding, “Emily thinks Pete is charming and they have flirtatious chemistry right now.”
Even prior to their romance, Ratajkowski seemed to have had her sights set on the comedian. During an appearance on Late Night with Seth Meyers the previous November, Ratajkowski said she could understand Davidson’s appeal and why women are very attracted to him. “He seems super charming,” she said. “He’s vulnerable. He’s lovely. His fingernail polish is awesome. He looks good.”
Related article: All The Photos From Emily Ratajkowski And Pete Davidson’s Courtside Date
Kim Kardashian (October 2021–August 2022)
Perhaps Davidson’s most high-profile relationship yet, the comedian and the mogul were first linked following Kardashian’s Saturday Night Live appearance, where they shared a stage kiss during their “Jasmine and Aladdin” skit (Kardashian later revealed the kiss gave her the feels). Afterward, the two embarked on a nine-month relationship that brought out a refreshingly comfortable new side of Kardashian since her split from ex-husband Kanye West.
“Pete has got to be literally the best human being I’ve ever met, like the best heart,” she said of Davidson on Hulu’s The Kardashians. “People always say, ‘Oh, he’s so funny.’ … That’s like, fourth on my list of why I like him. Always wants the best for people, can handle anything, always does it with grace. He’s really, really thoughtful, and humble, and just so genuine. I would say the perfect word to describe Pete is genuine.”
According to an E! source, the mogul broke things off with Davidson in August due to their busy work schedules and long-distance relationship, but the two remain on amicable terms.
Phoebe Dynevor (April–August 2021)
Rumors of Davidson’s romance with the Bridgerton star first swirled around March 2021, though Davidson officially confirmed their relationship the following month in a Zoom interview, during which he said he was currently with his celebrity crush. The pair eventually called it quits after just five months, reportedly due to their long-distance circumstances of him living in New York and her in England.
Kaia Gerber (October 2019–January 2020)
The then 18-year-old model shared a light four-month romance with the SNL comedian that ultimately fizzled out due to less-than-fortunate circumstances and timing. According to Page Six, Davidson was struggling a lot with his mental health at the time and had to check into a rehab facility. “She’s very young, and I’m fucking going through a lot and it was before I went to rehab,” Davidson told Charlamagne tha God during a February 2020 conversation on YouTube. “It just wasn’t the right place or the right time at all.”
Margaret Qualley (August–October 2019)
The pair’s short-lived summer fling began with a romantic outing in Venice, where the actress was promoting her then upcoming film, Seberg, at the Venice Film Festival. At the time, Qualley’s mother, actress Andie MacDowell, expressed her approval of Davidson and their romance, calling the relationship “nice.”
“[Margaret] has a beautiful relationship with him but I don’t want to step on her relationship too much,” she said in an exclusive with People that September, adding, “They have a nice relationship.”
Related article: Pete Davidson Thinks The Reason Women Like Him Is Because He’s a “Diamond in the Trash“
Kate Beckinsale (January–April 2019)
Several months following his called-off engagement with Grande, the then 25-year-old comedian began seeing the 45-year-old actress in a brief fling that blossomed around the time of the Golden Globes, where the two were spotted flirting at an after-party.
They eventually called it quits several months later due to reported incompatibilities surrounding their commitment levels. “Even though Kate has been in Hollywood for a long time, she struggled with the attention on her relationship with Pete,” an insider reportedly said, per Page Six. “He lives his life with his heart on his sleeve.”
Ariana Grande (May–October 2018)
In the same month that he confirmed his split from Cazzie David, the comedian shocked the world with a passionate new romance with singer Ariana Grande that ended almost as quickly as it began. After just five months, Grande ultimately broke things off with Davidson for reasons speculated to have been related to the tragic death of her ex-boyfriend, rapper Mac Miller.
Still, the pair’s brief time together yielded a handful of significant things: an engagement after just weeks of dating, a neck tattoo dedicated to Grande (Davidson eventually got it covered after their split), and the iconic, Davidson-inspired coined term, big dick energy.
Cazzie David (May 2016–May 2018)
Davidson shared his first and longest serious relationship with Cazzie David—the daughter of Curb Your Enthusiasm‘s Larry David—whom he likely first met back in February 2016 when her father hosted an episode of Saturday Night Live.
Exactly two years later, Davidson officially confirmed their split during a video interview with Complex. “We’re not together anymore,” he simply said. “Very talented girl, she’ll be great and she’ll be fine. Yeah, I think she’ll be okay.”
Related article: Pete Davidson Is In “Trauma Therapy” After Being Harassed Online By Kanye West
In her 2020 collection of essays, No One Asked for This, David opened up about the mental health issues she and Davidson struggled with throughout their relationship, as well as how she found out he was seeing Grande just a day after he broke things off with her.
This article originally appeared on Harper’s BAZAAR US.