A Complete Timeline Of Pete Davidson's Love Life

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."

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..."

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."

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."

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).

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!

The back and forth between Pete Davidson and Kanye West intensified when text messages between the two stars went public. In their exchange, Davidson told the rapper to leave him and Kim Kardashian alone. However, after West asked the comedian where he was, Davidson shared a selfie and wrote (via Pop Crave), "In bed with your wife." 

Despite their nasty feud, Davidson and Kardashian seemed to be going forward with their romance. During an episode of "The Kardashians," the reality star opened up about how she made the first move on Davidson. After getting his number, she told the cameras, "I wasn't even thinking like, 'On my God, I'm gonna be in a relationship with him.' I was just thinking, 'Heard about this BDE, need to get out there.'" In June 2022, they vacationed in Tahiti, with Kardashian sharing several photos on Instagram of the pair enjoying their time on the beach. However, by August, the two had called it quits because of their hectic schedules. A month after their split, Kardashian had nothing but good things to say about her ex. Speaking with Interview Magazine, she said, "He's literally such a good person, they don't really make them like him anymore."

Meanwhile, West was up to his old ways when he shared an Instagram post seemingly celebrating the end of the couple. The rapper uploaded a faux New York Times newspaper with the headline, "Skete Davidson Dead at Age 28," per TMZ. 

Pete Davidson and Chase Sui Wonders were co-stars in the horror film, "Bodies, Bodies, Bodies," having worked together on the movie around May 2021. Though their hockey outing in December 2022 was reportedly on friendly terms, Davidson and Emily Ratajkowski's romance had run its course around the same time. By the start of the New Year, Davidson and Wonders were romantically linked when photographs showed the pair kissing on an escalator at Universal Studios in Los Angeles.

In late January, the couple took a PDA-filled trip to Hawaii and were seen on the island again in March. Unfortunately, their return home after their romantic getaway hit a rough patch when the couple was involved in a car crash. According to TMZ, Davidson was behind the wheel of his Mercedes with Wonders in the passenger seat when he lost control of his car. The vehicle ended up hopping a curb, hitting a fire hydrant, and smashing into the side of a house in Beverly Hills. It was reported that Davidson was driving at high speed. Thankfully, the stars weren't hurt, and no one in the home was injured. There were no arrests made, as police reported that there were no signs of alcohol or drug use.