Pete Davidson: The comedian with a tragic childhood who has dated show business’s most powerful women

The unconventionally attractive comic has been romantically involved with celebrities such as Ariana Grande, Kim Kardashian, Kaia Gerber and Emily Ratajkowski

Pete Davidson in 2020.
Pete Davidson in 2020.Dimitrios Kambouris (Getty Images)

A year ago, in response to the rumors that Pete Davidson and Kim Kardashian were dating, a Twitter user posed a question: “[sic] did u tell ur girl u love her today or does pete davidson have to do it?” Such queries about the comedian’s life and loves have appeared frequently on the internet. Indeed, he was one of last year’s most closely analyzed celebrities. Most of the articles about him focus on his love life; he started 2022 by dating with Kim Kardashian and ended the year with model Emily Ratajkowski. As of 2023, he is reportedly seeing Bodies Bodies Bodies co-star Chase Sui Wonders. But why are the internet and the media so obsessed with Pete Davidson?

Most people who are familiar with Davidson’s romantic life hardly know why he’s famous in the first place. In 2013, at just 20 years old, he joined Saturday Night Live, making him the wunderkind of American comedy. His childhood, which was shaped by the death of his father, a firefighter, in the September 11, 2001, terrorist attacks, also made headlines. Pete was only seven years old at the time of his father’s death. He has turned that tragedy into comedy, which has been therapeutic for him and off-putting for others. For example, on a Comedy Central special, he told Justin Bieber, “I always regretted growing up without a dad … until I met your dad, Justin. Now I’m glad mine’s dead.”

Pete Davidson and Ariana Grande at the 2018 MTV Video Music Awards gala.
Pete Davidson and Ariana Grande at the 2018 MTV Video Music Awards gala.Nicholas Hunt (Getty Images for MTV)

But it was in 2018 that he shot to stardom thanks to his relationship with singer Ariana Grande. At the time he met the singer, he was dating Cazzie David, comedian Larry David’s daughter. The internet informed David that her boyfriend was now seeing Ariana Grande. Twenty-four days later, Grande and Davidson were engaged. In the summer of 2018, the public was riveted by their loving messages on Instagram, photos of them kissing on the street, Davidson’s tattoo tributes to his girlfriend (which covered up Cazzie David’s face) and the little pig they adopted as a pet. Grande included a song titled Pete Davidson on her album Sweetener. But things went sour when, weeks later, the singer’s ex-boyfriend Mac Miller died of a drug overdose; Davidson’s and Grande’s Instagram pages were flooded with messages that blamed them for Miller’s death, and the couple broke off their engagement (which led to the biggest hit of Grande’s career, Thank U Next).

Days later, Davidson posted an alarming message on Instagram, stating: “I really don’t want to be on this Earth anymore.” The post alerted the New York Police Department and Grande, who went to her ex-boyfriend’s building and left him a public message on Instagram reading: “I’m downstairs.” The singer even responded to people who asked her why she didn’t call him on the phone directly (she explained that she didn’t have his number). That night, the internet was on tenterhooks over the possibility of a live-streamed suicide, but it ended up as one of the all-time greatest examples of exhibitionism in celebrity culture. The Washington Post published an article about the incident, headlined: “To understand culture in 2018, you must understand Ariana Grande and Pete Davidson.”

At a time when celebrities struggle to protect their privacy, Davidson brazenly puts his life on full display, treating the entire internet as if it were his Instagram feed. Each of his relationships with famous women has followed the same pattern: he French-kissed Kate Beckinsale at a basketball game; held hands with Margaret Qualley (Andie MacDowell’s daughter) at the Venice Film Festival; attended tennis matches with Phoebe Dynevor (from Bridgerton) where they wore pendants with each other’s initials; and posed at parties with Kaia Gerber, the daughter of model Cindy Crawford. But despite these public displays of affection, all these relationships ended within six months. With each new relationship, the mystery of Pete Davidson has deepened: he’s not conventionally handsome, and many wonder what is the secret to his success.

Pete Davidson shows off his many tattoos during a shoot in New York in 2019.
Pete Davidson shows off his many tattoos during a shoot in New York in 2019. Bobby Bank (GC Images)

Some claim that Pete Davidson is a millennial version of Casanova whose sexual prowess is irresistible to women who – according to the prejudices of a status-obsessed society – are out of his league. Or one might describe Davidson’s magic differently: one Twitter user coined the phrase “big dick energy” (BDE) to refer to people who are so self-assured that they are always relaxed and have nothing to prove. This is an attitude more than anything. For instance, Rihanna and Cate Blanchett have BDE. Cardi B has built a career based on it. And the consensus seems to be that Pete Davidson has BDE in spades. In his case, apparently, it’s not just a metaphor: Ariana Grande posted that he measured 10 inches (25 centimeters) in a tweet that she promptly deleted, but not before people took note.

Davidson brushed it off as a joke. “It’s just simply not true,” he explained. “[Ariana] has little tiny little hands. She has just very little hands. Everything’s fucking huge to her. She did that so that every girl that sees my dick for the rest of my life is disappointed.”

One Reddit thread discussing the mystery of Pete Davidson’s appeal drew 2,800 comments. People observed that “he seems like the kind of guy who isn’t afraid to hold a woman’s purse,” “he’s basically a golden retriever of men,” and “he’s like your weed dealer whom you feel safe around for some reason and when he starts cracking jokes, you realize you’d hook up with him.” Singer-songwriter Olivia Rodrigo, born in 1993, singled him out as her “celebrity crush.” Singer Dionne Warwick, born in 1940, tweeted that she would be “dating Pete Davidson next.” A year before she started dating him, Emily Ratajkowski offered her own theory on Late Night with Seth Meyers: “Pete – he’s got the height. Obviously women find him very attractive […] he seems super charming. He’s vulnerable. He’s lovely. His fingernail polish is awesome. He looks good! [And he has a] super great relationship with his mom.”

Pete Davidson receives a kiss from British actress Phoebe Dynevor in London in the summer of 2021.
Pete Davidson receives a kiss from British actress Phoebe Dynevor in London in the summer of 2021.Paul Edwards (WireImage)

Pete Davidson’s success has also been analyzed in terms of the new masculinity, that is, men who are in touch with their emotions and honest about their mental health. As actress Tommy Dorfman wrote in Paper magazine, “in the end…if I had to sum up [Davidson’s appeal] in one word it’d have to be heart: a massive – perhaps wounded – eagerly available heart inside the body of a boy I would’ve expected to beat me up in high school.” For the magazine feature, Davidson posed as a tattooed, penis-less Ken doll surrounded by antidepressants, parodying his public image.

Davidson’s personality also fits with the nice guy archetype, in which a man is kind to women until one rejects him, whereupon he unleashes his misogyny. In contrast, Pete Davidson genuinely likes women. “When I’m in a relationship […] I treat the person I’m with like a princess,” he explained. “But sometimes when you put so much on someone, it overwhelms them, and then they don’t know if they could come close to that.”

Christine Taylor, Ben Stiller, Pete Davidson, Emily Ratajkowski, Jordin Sparks and Dana Isaiah at a Memphis Grizzlies–New York Knicks basketball game at Madison Square Garden on Nov. 27. It was Davidson and Ratajkowski's first public appearance as a couple.
Christine Taylor, Ben Stiller, Pete Davidson, Emily Ratajkowski, Jordin Sparks and Dana Isaiah at a Memphis Grizzlies–New York Knicks basketball game at Madison Square Garden on Nov. 27. It was Davidson and Ratajkowski's first public appearance as a couple. Jamie Squire (Getty Images)

Despite his magnetism, the comedian has suffered a great deal. Davidson was diagnosed with multiple personality disorder. He attempted suicide when he was just nine years old and engaged in self-harming behavior (for example, he tore out all of his hair). A group of psychologists monitored him for years to study the aftermath of 9/11. The comedian was reluctant to reveal that he left Saturday Night Live after seven seasons because he felt the show was making fun of him. Everyone likes to side with an underdog, and Pete Davidson is the underdog who best represents the current decade.

The comedian and the influencer

Davidson and Kardashian first appeared together as a couple on a roller coaster at an amusement park in Staten Island, the New York borough where he grew up. His childlike enthusiasm won over many fans. It’s clear that fame appeals to him, but rather than being desperate to become a celebrity, he seems awed by the magnitude of fame and how it works. For example, he was impressed that when Grande wanted an unusual pet, she was able to get one right away. “[Ariana] was like, ‘I want a pig!’ And then an hour later, it was just there…You know what I mean? I’m still trying to get a Propecia refill ... [and] this girl got a pig in an hour,” he said. Now, Pete Davidson is a celebrity in his own right.

Pete Davidson and Kim Kardashian at the 2022 Met Gala.
Pete Davidson and Kim Kardashian at the 2022 Met Gala. Dimitrios Kambouris (Getty Images for The Met Museum/)

Most of Davidson’s partners had just endured traumatic breakups when they began dating him. Ariana Grande described her relationship with the comedian as “an amazing distraction. It was frivolous and fun and insane and highly unrealistic, and I loved him, and I didn’t know him.” In Vogue, journalist Emma Specter argued that Ratajkowski “deserves to have a little post-divorce fling.” In The Guardian, Arwa Mahdawi referred to Davidson as the “ultimate rebound guy,” and went on to note that “he perfectly understands his role. He’ll hang out with your kids! He’ll take you to dinner at his favourite place in Staten Island. He’ll provide lots of photo ops for your PR people! And then, when the relationship has run its course, he backs away without any drama. He’ll quietly get the tattoos removed. He won’t say anything nasty to the press. He’ll move on without any venom.”

Such unbalanced relationships cast Pete Davidson as something of a tragic figure. According to rumors, Davidson and Kardashian broke up because he wanted to start a family (his lifelong dream is to be a father) and she didn’t. A few months after they started dating, he got three tattoos dedicated to her: the names Jasmine and Aladdin next to the infinity symbol (they met while recording a Saturday Night Live sketch that parodied Aladdin), the initials of Kardashian’s four children with Kanye West and the phrase “my girlfriend is a lawyer,” referring to the law degree she earned in May last year. He described those tattoos as “scars.” It’s as if he was already anticipating the pain of a breakup. His body is a map of his traumas. If he ever forgets them, the internet will certainly be there to remind him.

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