A Recap of Pete Davidson's Romantic History: From Cazzie David to Emily Ratajkowski

pete davidson at knicks game
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ET is taking a look back at the comic's complex and high-profile love life.

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 -- most recently with a high-profile dalliance with Emily Ratajkowski following a long and seemingly serious romance with Kim Kardashian.

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.

Cazzie David -- May 2016 - May 2018

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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."

Ariana Grande -- May 2018 - October 2018

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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 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."

Kate Beckinsale -- Jan. 2019 - Apr. 2019

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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.

Margaret Qualley -- Aug. 2019 - Oct. 2019

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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. 

Kaia Gerber -- Nov. 2019 - Jan. 2020


Rumors of Davidson's 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."

Davidson went on to say that he was planning on going to rehab during the show's Christmas break. Shortly after, rumors surfaced that Davidson and Gerber had quietly split up.

Phoebe Dynevor -- March 2021 - August 2021

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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.

Kim Kardashian -- Nov. 2021 - Sept. 2022

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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 -- Nov. 2022 - Dec. 2022

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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."

For more on Davidson's high-profile dating history, check out the video below.