A Complete Timeline Of Pete Davidson's Love Life

The following article discusses substance abuse and mental health.

Few "Saturday Night Live" stars in the modern era have become genuine tabloid sensations quite like Pete Davidson. The goofy comedian from Staten Island lost his firefighter father on 9/11, and his willingness to speak openly about his trauma, his borderline personality disorder diagnosis, and his struggles with substance use has endeared him to millions of fans. "I've been in and out of mental health facilities since I was 9," he told Variety, and he frequently shares updates on his sobriety (or lack thereof) on "Weekend Update."

However, there's something else about the funnyman that makes him fodder for gossip columnists and paparazzi... and no, we're not (just) talking about a certain body part that, we promise, will be discussed later on. Davidson's love life is the stuff of pop culture legend; the Daily Mail calls him "the world's most unlikely Lothario," while the New York Post compared him to the iconically-promiscuous actor Warren Beatty. Fans pore over details of Davidson's relationships with the bevy of beautiful women he's been linked to, speculating about what, exactly, he does to make them like him. "Please stop pretending that Pete Davidson isn't hot," begs The Daily Beast, while a viral tweet suggests that maybe he has "a nice personality."

Whatever his secret, it can be tough to keep straight all of the romances Davidson has made headlines for; fear not and read on for a complete timeline of Pete Davidson's love life.

His first celeb girlfriend was Carly Aquilino

Pete Davidson joined the cast of "SNL" in 2014, at the young age of 20. He received raves for his first appearance on the show, including from "Roots" drummer Questlove, who tweeted, "This Kid Is A Star." Questlove was correct: Davidson rocketed to instant fame on the show, and within months of joining the cast, he was dating a fellow celeb. He paired up with Carly Aquilino, a comedian who starred on MTV's "Girl Code," in 2015. Davidson made regular appearances on the corresponding show "Guy Code," so it's likely they met in that capacity. MTV proudly posted a roundup of Instagram photos of the couple... most of which have since been deleted, as one does after a breakup.

The two seem to have remained friends, even though they split in 2015. Years later, Aquilino had a part in "The King of Staten Island," which Davidson co-wrote with director Judd Apatow. She thanked him on Instagram for the opportunity and wrote that she was "very proud of everyone who worked so hard making [the film]. Thank you Pete & @juddapatow for letting me be apart [sic] of it."

In an interview with Charlamagne Tha God, Davidson reflected on some of his exes. He perked up at the mention of Aquilino, telling the host, "Oh, we love Carly! She's the best. We're cool friends. We actually hang out all the time. ... She's honestly one of the coolest chicks I think I've ever met."

Cazzie David's dad loved Pete

Pete Davidson's first truly high-profile relationship was with Cazzie David, daughter of comedian and actor Larry David. They dated for several years, and Davidson credited David with helping him stay sober. "I'm very lucky. She's very, very supportive," he told Entertainment Tonight. For her part, David told the outlet that her father liked that she was dating a comedian. "He loves it because he feels like the only people he can talk to are people who also make jokes," she said. "It worked out very well."

Davidson loved David's father back, telling People, "He's the sweetest man in the world; he's the coolest... I listen to everything he says very carefully because you want to retain it all."

Unfortunately, the relationship was not to last, and Davidson's next relationship would invite a heck of a lot of scrutiny about how his romance with David had ended. According to TMZ, they were "on a break" when Davidson found a new girlfriend: pop superstar Ariana Grande. At the time, in public, David seemed to have taken the news reasonably well, posting on Instagram, "Been in Africa, what'd I miss ??" However, in her 2020 essay collection "No One Asked For This," she revealed that she found herself "screaming in agony" over the situation.

Davidson, who covered up a tattoo he'd gotten during the relationship, told Insider that he was happy for the success of her book. "We're cool. I wish her nothing but the best," he said.

His whirlwind romance with Ariana Grande

Pete Davidson totally didn't cheat with Ariana Grande... they were on a break! Ditto Grande and her ex, rapper Mac Miller, whom she split from weeks before linking up with the "SNL" star. Everyone was obsessed with this surprising collision of late-night TV comedian and world-famous pop superstar, and the early days of this new couple dominated the headlines in 2018. Those first few weeks were a flurry of speculation and rumor, plus a ship name to rival the likes of Bennifer and Brangelina: GrandSon. Bustle noted that people on Twitter, as they often do, had a lot of feelings.

GrandSon was a bona fide media frenzy, with one particular photo of the couple going mega-viral. It depicted the duo out on a walk in New York City, with Grande in an oversized bright yellow hoodie, licking a lollipop as she stared up at her much-taller boyfriend, her trademark high pony on full display. Though — spoilers — the relationship wouldn't last until Halloween, this photo sparked a costume craze

In a sign of troubles ahead, a fan accused Grande of being responsible for Mac Miller's DUI charge shortly after she got with Davidson. She clapped back on Twitter. "how absurd that you minimize female self-respect and self-worth by saying someone should stay in a toxic relationship," she wrote in a NotesApp statement. "I am not a babysitter... I will continue to pray from the bottom of my heart that he figures it all out..."

Pete and Ari got engaged quickly

Mere weeks after they officially got together, Pete Davidson and Ariana Grande made GrandSon official with a reported $93K engagement ring. Pete confirmed the rumors on The Tonight Show with Jimmy Fallon, glowing as he talked about how lucky he felt. "I feel like I won a contest. It's f***ing lit, Jimmy," he told his fellow "SNL" alum. "It's so funny walking down the street, because dudes are walking by and they [tip their hats]."

The twosome got a number of tattoos to mark their relationship. Among others, Davidson inked Grande's "Dangerous Woman"-era bunny ears on his neck; Grande got "pete" on her ring finger; and she added an "8418" tattoo to match his, "commemorating his late father's FDNY badge number," per People.

The "Positions" singer repeatedly defended her fiance against trolls, speaking out in his defense after a Barstool Sports blogger said Davidson had "butthole eyes." In a reference to the fact that Davidson has Crohn's disease, Grande replied (via BuzzFeed), "y'all do kno this man has an auto immune disease ...... right?" She also included an interlude called "pete davidson" on her album "Sweetener," released a few months into the relationship. The refrain of the song sees Grande repeating to herself contentedly, "I'ma be happy, happy." When fans questioned the wisdom of naming a song after someone she'd only been with a few months, she clapped back, tweeting, "life's too short to be cryptic n s**t about something as beautiful as this love I'm in."

Pete Davidson's 'BDE' sparked a cultural movement

GrandSon's longest-lasting contribution to pop culture is undoubtedly the fallout from a tweet Ariana Grande penned about Pete Davidson's, um, endowment. Deep in love, Grande replied to a fan who had asked how long the "pete davidson" interlude on "Sweetener" would be. Grande talked about a different length entirely, teasing (via The Verge), "like 10 inches?" before acknowledging the interlude.

The tweet found itself at the center of a perfect storm of pop culture. Several weeks earlier, a viral tweet had mentioned late chef Anthony Bourdain's "big dick energy." After someone else on Twitter picked up the term and applied it to Davidson, writing (via The Cut), "Pete davidson is 6'3 with dark circles, exudes big dick energy, looks evil but apparently is an angel, and loves his girl publicly," Big Dick Energy — BDE for short — was suddenly everywhere. The phrase spawned think pieces, explainers about the psychology of the phenomenon, a GQ style guide to help you look like you have BDE, and even a spin-off meme about girls with Horse Girl Energy.

After their eventual breakup, Grande doubled down in the music video for "thank u, next," writing "HUUUUUGE!" next to Davidson's pic. He wasn't a fan. In a stand-up set the following year, he said (via Elle), "I don't like that she talked all that s**t for my penis. ... Why would she tell everyone that I have a huge penis? So that every girl who sees my dick for the rest of my life is disappointed."

Mac Miller's death led to the end of GrandSon

In September 2018, Ariana Grande's ex, rapper Mac Miller, passed away from an accidental overdose. Grande was still with Pete Davidson at the time, but Davidson later said in an interview with Charlamagne tha God that he knew then that the engagement was over. "I was like, 'Listen, I get it, do whatever you've got to do, I'll be here,'" he recalled. "I think I said, 'I'll be here until you don't want me to be here.' I pretty much knew it was around over after that." Davidson clarified that Grande's public grieving around the time was genuine, insisting, "All I do know is, is that she really loved the s**t out of him, and she wasn't putting on a show or anything."

GrandSon ended their five-month whirlwind relationship in October 2018, via People. A source in Grande's camp confirmed what much of the world had been thinking: "It was way too much too soon." Shortly after they ended things, Grande released "thank u, next," a song that calls out her exes by name and rattles off the things she learned from each one. "I almost got married, and for Pete I'm so thankful," she sang.

Around that time, Davidson found himself embroiled in controversy after he mocked Rep. Dan Crenshaw on "SNL" for wearing an eyepatch. The Congressman joined Davidson on "Weekend Update" so that Davidson could apologize; during the segment, the Congressman's phone rang, playing Grande's song "breathin" (via ET Canada).

Pete packed on the PDA with Kate Beckinsale

After the dissolution of his engagement with Ariana Grande, Pete Davidson soon rebounded with "Underworld" star Kate Beckinsale, twenty years his senior. The two were spotted making out at a Rangers game while "Queer Eye's" Antoni Porowski looked on uncomfortably, sparking a wave of internet jokes about what he must have thought of the PDA during the awkward paparazzi shots. Shortly thereafter, Davidson confirmed the relationship on "SNL," making fun of people who are interested in their age gap — while they were together, Davidson was 25 and Beckinsale was 45. "Apparently people have a crazy fascination with our age difference. But it doesn't really bother us," he said before rattling off a list of other famous people who have dated younger, including Leonardo Di Caprio and then-president Donald Trump.

Beckinsale also spoke about their relationship without mentioning him by name, describing what a difference their coupling was for her in a Los Angeles Times interview. "I've never been in this position before — never dated anybody who comes with their own bag of mischief," she said. She clarified that she didn't like having people staking out her house to spy on her relationship, calling it "old-fashioned" and "a little bit tired."

They broke up in May 2019 after four months of dating, a source confirmed to Us Weekly. Over two years later, Beckinsale liked a tweet (via InStyle) suggesting the way Pete dates beautiful women is thanks to his "nice personality."

Pete and Margaret Qualley had 'a beautiful relationship'

Pete Davidson had a busy 2019 after breaking up with Kate Beckinsale. A few months later, in August of that year, Us Weekly confirmed that Davidson was in a new relationship with "Once Upon a Time... in Hollywood" star Margaret Qualley. They were spotted during the Venice Film Festival, going on dates around town and attending screenings together, as Qualley was there for the premiere of her film "Seberg," which starred Kristen Stewart.

Qualley's mother, actor Andie MacDowell, told People that she had not met the "SNL" star yet, but that she very much approved of their union. After appearing to mix up the difference between FaceTiming and sending a video — stars' parents... they're just like ours! — MacDowell explained that she didn't want to be pushy with her daughter. "She has a beautiful relationship with him," she said, "but I don't want to step on her relationship too much."

As quickly as the romance began, it was over. Qualley and Davidson split after two months together, with a source telling Us Weekly that although they had ended the relationship, "They remain friends." Davidson told Charlamagne tha God that Qualley was a "beautiful soul," adding, "She'll win an Oscar. She's gonna win an Oscar for sure. She's so talented."

Pete Davidson and Kaia Gerber both regret dating

In the last few months of 2019, Pete Davidson found himself on the other side of an age-gap relationship when he dated Kaia Gerber, model daughter of Cindy Crawford, who was newly 18 at the time. "Kaia expressed she loved Pete's personality. She thinks he is charming and is very intrigued," an insider told E! News as word of their budding romance spread online.

In his sit-down with Charlamagne tha God, Davidson recalled that the relationship was a bad idea. "We were dating for a few months, and she's very young, and I'm f***ing going through a lot," he reflected. "She should be having fun and s**t. She shouldn't have to worry about some dude that just, like, has issues and s**t." ​

It seems that Gerber agrees that the couple wasn't right. "I tended to date older people because those were the people I was around," she told Vogue a few years later, evidently referring to Davidson. "And I got put in situations where one day I'd wake up and be like, 'How did I get here? I have no idea what I'm doing, and I need help.'"

Shortly after splitting, Davidson spent some time in rehab. He joked on "SNL" that he was taking "the kind of vacation where, like, insurance pays for some of it, and they take your phone and shoelaces," and then he confirmed his stay in a stand-up set a few months later.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

His long-distance relationship with Phoebe Dynevor didn't last

After things fell apart with Kaia Gerber, Pete Davidson took some time off from dating. In April 2021, Davidson said in a virtual college Q&A that he was with his celebrity crush (via ET), not naming her specifically but seeming to confirm rumors that he was seeing someone new. That someone turned out to be "Bridgerton" star Phoebe Dynevor; fans caught on to the fact that the identically-initialed stars wore similar necklaces bearing their monogram (per People). Davidson flew out to the U.K. to visit her, and an Us Weekly source confirmed that they were dating long-distance after having met in New York. 

Their first public appearance came a few months later, when the "Big Time Adolescence" actor took a page out of his own playbook and showed off some PDA with his new girl at a sports game. In this case, cameras captured the two cuddled up at Wimbledon (via Insider). Davidson kissed her on the forehead, and she returned the affection with a kiss on his cheek.

The Sun confirmed their split in August 2021, after about five months together, due to separate work commitments — for him, a movie and a new season of "Saturday Night Live" in New York; for her, the next season of "Bridgerton" in the U.K.

Pete Davidson and Kim K confirmed their relationship

Though Page Six reported that Kim Kardashian's estranged husband Kanye West was in attendance when she hosted "SNL" in October 2021, it seems that someone else in the room at 30 Rock caught her eye: Pete Davidson. During one of the show's highlights, Kardashian played Jasmine to Davidson's hapless Aladdin, and they kissed.

Shortly thereafter, the twosome were spotted holding hands at a Halloween event at Knott's Berry Farm, a theme park outside L.A. Pictures of the couple riding a rollercoaster went viral instantly, because, what a pair! However, a source told ET that they were simply friends, running in similar circles because of Davidson's friendship with Travis Barker, who became engaged to Kim's sister Kourtney.

Soon, though, news broke on TMZ that they had attended a secret dinner in Davidson's hometown on Staten Island, and they were spotted around NYC several times more. Finally, in November 2021, they appeared to confirm their relationship on a public stroll in Palm Springs, near Kris Jenner's home. In photos published in the Daily Mail, Pete was spotted wearing Skims loungewear, Kim's brand, while they held hands. Ye was reportedly upset with the news; a source told HollywoodLife he was particularly insulted that Davidson was invited to Jenner's house. Davidson had previously addressed Kanye on "SNL," saying that he wished he'd told the rapper not to wear a MAGA hat on the show because it might upset Kim. Seems like they're even!