Pete Davidson’s love life has had more twists, turns, surprises and shocking ends than most soap operas, and it is thrust into the spotlight every time the Saturday Night Live alum is spotted holding hands with someone new.
The so-called “secret” to Davidson’s magnetic charm has been debated and dissected by celebs, co-stars, friendly exes and nearly everyone on Twitter endlessly. It usually boils down to either “he’s super funny,” or “he’s super sweet” or a third, more personal and indiscreet option that everyone knows so we don’t need to mention here.
Regardless of the reasons behind his undeniable charisma and attractiveness, Davidson’s romances have stolen the spotlight time and again — from his engagement to Ariana Grande, to a long and seemingly serious romance with Kim Kardashian, to, most recently, his budding romance with Outer Banks star Madelyn Cline.
ET is taking a look back at Davidson’s dating history and going through each of his headline-grabbing romances over the past several years.
Davidson briefly dated fellow comedian Carly Aquilino in 2015. The 27-year-old Girl Code star appeared to have a reaction to his engagement to Ariana Grande in June 2018 when she took to her Instagram Stories after the news broke, sharing a pointed text message exchange she had with a friend who wrote, “I know I’m the 9 billionth person to text you about this but… I can’t.” Aquilino responded “HAHHAHAHAAH,” and wrote, “MY DAY IN A TEXT MESSAGE” over the screenshot before sharing it with her followers.
One of Davidson’s first long-term and serious celeb romances was sparked with Cazzie David — the daughter of comedian Larry David — in May 2016. ET caught up with Davidson in April 2017, at the Natural Resources Defense Council’s Stand Up For The Planet Benefit gala in Los Angeles, where the two walked the red carpet together. Davidson praised his then-girlfriend, telling ET, “She’s the most beautiful girl in the world, look how lucky I am. She’s so smart, look how smart she is. She is a very, very wonderful lady.”
The young sketch comic also credited David for helping him stay sober after a long struggle with substance abuse, explaining, “I’m very lucky. She’s very, very supportive.”
However, in May 2018, Davidson revealed that they’d split up during an interview with Complex’s Open Late with Peter Rosenberg. Davidson revealed, “We’re not together anymore,” but had nothing but kind words for his ex, telling Rosenberg, that she’s a “very talented girl” and that “she’ll do great, she’ll be fine.”
Davidson redefined “whirlwind romance” with his relationship with Ariana Grande. The pair began dating very shortly after his split with Cazzie David, and then revealed they’d gotten engaged just one month after they first started dating.
Their romance made headlines constantly, and the pair spent a lot of time in the spotlight. Grande even released a song called “Pete Davidson.” The comedian appeared in a “Weekend Update” segment on SNL, where he joked about their relationship being somewhat reckless. Then, in October, the pair actually did break up.
According to Davidson, a significant part of the reason for their split was the shocking and tragic death of Grande’s ex-boyfriend, Mac Miller, who died of a drug overdose in September 2018. Davidson explained to Charlamagne Tha God in February 2020 that Miller’s death had an immediate effect on their engagement. “I was like, ‘Listen, I get it, do whatever you’ve got to do, I’ll be here,'” Davidson recalled how he supported Grande as she mourned her ex. “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 and Kate Beckinsale began attracting paparazzi attention in January 2019, after first sparking romance rumors at a Golden Globes party. They were subsequently spotted locking lips in public — multiple times.
In March 2019, Beckinsale briefly addressed their whirlwind romance in an interview with the Los Angeles Times, where she commented on the media scrutiny that comes with dating someone like the Saturday Night Live star. “I’ve never been in this position before,” Beckinsale admitted. “Never dated anybody who comes with their own bag of mischief.”
The next month, the pair had moved on, but a source told ET at the time that they remained friends.
In one of Davidson’s quieter romances, the Meet Cute star was romantically linked to Once Upon a Time… in Hollywood actress Margaret Qualley for just a few, hand-holding months. Davidson and Qualley sparked romance rumors in August 2019 and were spotted together multiple times throughout September, and in different countries — namely, in Italy, where they attended the Venice Film Festival. However, the pair called it quits in mid-October.
Qualley — the daughter of actress Andie MacDowell — went on to marry Jack Antonoff in August 2023.
Rumors of Davidson’s next nepo baby romance, with Kaia Gerber — the daughter of iconic supermodel Cindy Crawford — began to swirl at almost the exact moment news broke that he and Qualley had called it quits. Their romance was confirmed in November 2019. They were spotted hanging out a few times, and Davidson even addressed the controversy generated by their relationship during an episode of SNL in December 2019.
Speaking to “Weekend Update” anchor Colin Jost — and referring to Jost’s engagement to Scarlett Johansson — Davidson quipped, “You get to date a famous woman and everyone’s delighted, but I do it and America wants to punch me in the throat.” Davidson went on to say he didn’t understand why people were so mad about it because he was about the best choice Gerber could have when it came to dating guys who look like him. “There’s a million guys who look like me and I’m the only one who has a job. It’s just me and Tyga.”
The pair were last publicly seen together in Miami, Florida, for a friend’s wedding and had reportedly split by January 2020. Gerber went on to date Austin Butler, and was on his arm the night he won the Best Actor Academy Award for his titular role in Elvis.
Rumors that Bridgerton star Phoebe Dynevor and Davidson were dating first started swirling in March 2021, when an eyewitness told ET that the pair was allegedly holding hands while in the United Kingdom together. That same month, a source told ET that Davidson and Dynevor “really hit it off” after meeting at a New York City gathering. The source added that Davidson and Dynevor “traveled between New York City and England to spend time with one another while also working.”
In July 2021, the cute stars looked totally smitten with each other while attending day six of the Wimbledon Tennis Championships at the All England Lawn Tennis and Croquet Club, in one of their most public outings together. However, by mid-August, ET learned that they had gone their separate ways due to their hectic shooting schedules in different parts of the world.
In a September 2023 interview with Elle, Dynevor said she felt she was “naive” about the public attention her relationship with Davidson would receive.
“I didn’t think anyone would care,” she admitted. “I was just being a young woman and dating and somehow that provokes a conversation. There were lots of hard lessons I had to learn through basically just having a personal life. You realize, ‘Oh, I can’t live my life in the way that I used to. I have to keep my cards slightly closer to my chest.’ There was a time, for example, when I’d post anything on my Instagram, and now I’m very, very careful about what I put out into the world.”
In the romance that would finally overshadow Davidson’s brief engagement to Ariana Grande, the comic began dating Kim Kardashian in October 2021 — following news that she’d split from husband Kanye “Ye” West, and after Kardashian and Davidson shared an on-screen kiss during the reality star’s SNL hosting debut.
Every single aspect of their romance was covered by the press and obsessed over by fans — and this reached a fever pitch when West began feuding with Davidson on social media, insulting, harassing and threatening him routinely for weeks. Davidson did his best to largely ignore the jabs and kept his relationship largely private. The pair even attended the Met Gala together in one of the largest public displays of their romance.
When The Kardashians premiered on Hulu in April 2022, fans got more insight into the couple’s romance, as Kardashian revealed she’d made the first move with Davidson, and hinted that she’s had the best sex of her life with the comedian. However, the pair ended up splitting in September 2022. A source told ET at the time that “the distance has been hard and things were starting to fizzle out.”
Emily Ratajkowski and Davidson were first linked in November, two months after she filed for divorce from her ex, Sebastian Bear-McClard and three months after Davidson’s split from Kardashian. After a source confirmed the romance to ET, the duo was photographed together for the first time shortly after and went on to have a public date night. That all happened around the same time that a source told ET that the model found the SNL alum to be “super charismatic, funny, and a good rebound.”
However, things seemed to come to an end before they really started. A source told ET on Dec. 27, that the model and the comedian “have been doing their own things and were never serious.” The source added, “Emily finds Pete hysterical, and he thinks she’s smoking hot, but they’ve both been living their lives and not putting any pressure on anything.”
Davidson and Wonders initially met on the set of Bodies Bodies Bodies in 2021, in which she plays his love interest. They were first linked together in December 2022, when they hit up a New York Rangers game at Madison Square Garden, and they confirmed their romance with a kiss the following month while at Universal Studios Hollywood.
In April 2023, Davidson gushed over Wonders at his Bupkis premiere — in which she also co-starred — in New York City, telling ET she’s “the best.”
Wonders returned the favor in May while offering a rare look at their relationship, telling Nylon magazine that their partnership was a “sacred” one.
After about nine months, however, a source confirmed their split to ET in August 2023, not long after ET confirmed that Davison had entered rehab just weeks after being charged with misdemeanor reckless driving following a March car crash. A source told ET that the Saturday Night Live alum was in rehab for mental health issues and is working to “get back on track.”
Us Weekly was first to report Davidson’s rumored romance with Outer Banks star Madelyn Cline in September 2023, sharing that the pair “spent the night together at the Beverly Hills Hotel and then had a breakfast together there the next morning.”
According to the outlet, Davidson and Cline were “really low-key and kept things casual, wearing baseball hats.”
A source told ET that same month that the couple were in fact dating and had recently spent a whirlwind 24 hours together in Las Vegas. “They have been hanging out and spending time together when they can and really like each other,” the source said.
As for their Vegas getaway, the source added, “They traveled with a group of friends to Vegas, but enjoyed alone time together too. The two of them stayed in the Crockfords Entertainment Suite at Resorts World, while their friends stayed in another suite. During their visit, Pete and Madelyn hung out at the resorts’ Alle Lounge on 66 just the two of them, while the rest of their group went off to gamble. Everyone had a great time.”
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