Over the years, Pete Davidson has gone from the youngest current cast member on Saturday Night Live to Hollywood’s most eligible bachelor. At least, that’s how it seems considering his relationships with a slew of beloved stars. Davidson’s most significant relationship to date — his engagement to Ariana Grande, which ended just months after it was announced in 2018 — has made fans wonder whether he’ll find love that’s as obsessed over by the masses in the future.
We don’t have a crystal ball to find out if Davidson’s next girlfriend will be his last, but we can walk through the comedian’s romantic past, from his earliest known romances to his most recent “hang out” with a supermodel’s daughter.
Carly Aquilino, 2015
The Girl Code comedian reportedly dated Davidson around 2015. Three years later, when word broke of Davidson’s engagement to Grande, Aquilino seemingly hinted that she was well aware of the proposal in an Instagram story.
Years after their reported romantic relationship, Aquilino and Davidson were spotted hanging out again in February of 2019 at a comedy show on Long Island, but it seemed that the interaction was strictly platonic.
Cazzie David, 2016 to 2018
Actress, writer, and producer David — who also happens to be the daughter of Curb Your Enthusiasm’s Larry David — dated Davidson for two years, and their relationship ended shortly before his whirlwind romance with Grande began. (David was in Africa at the time and asked her Instagram followers what she “missed” while she was away.) As Davidson predicted in speaking about their breakup, “[Cazzie] will be fine.” Not long after the split, David scored a pilot order for her series Half-Empty.
Ariana Grande, May 2018 to October 2018
Shortly after Davidson publicly stated he and David were no longer dating, reports that he is “casually” dating pop star Grande broke. (If you’re a Pariana truther, you can adjust the timeline accordingly.)
The couple was spotted on Instagram in corresponding Harry Potter sweatshirts, and got matching tattoos before they revealed their engagement in June. However, in October of 2018 — after the death of Grande’s ex-boyfriend Mac Miller — Grande and Davidson split up, and sources claimed the whole relationship was simply too much, too fast. Pariana fans mourned, and in February of 2019, Grande released her ex appreciation song “thank u, next,” which named Davidson.
Kate Beckinsale, January 2019 to April 2019
After Davidson and Beckinsale flirted at a Golden Globes after-party in January of 2019, the two were spotted canoodling all over New York City. They even made out at a hockey game at Madison Square Garden. To further solidify their relationship, Davidson went on SNL’s "Weekend Update" to shut down haters who took issue with the couple’s 20-year age difference. Alas, by April of 2019, the two were done, with sources blaming the “long distance” for driving them apart.
Margaret Qualley, August 2019 to October 2019
In August, reports insisted that Qualley and Davidson had been seeing each other for a few months, and that the Once Upon a Time in Hollywood actress was “excited” about her new boo. A month later, Andie MacDowell, Qualley’s mom, confirmed to People that the two have a “beautiful” and “nice” relationship. By October, though, that beautiful and nice relationship was apparently over, and a source for Us Weekly claimed they would “remain friends.”
Kaia Gerber, October 2019-?
Right now, the only thing that Davidson and 18-year-old model Gerber are doing is “hanging out,” according to a source for Page Six, after paparazzi pics caught Davidson leaving her apartment. Gerber likely met Davidson at the Alexander Wang fashion show, where Gerber walked and Davidson made his runway debut.