Pete Davidson's Relationship History: Who He's Dated

Alright guys, let's dive into the fascinating world of Pete Davidson's love life! This guy is known for a lot of things – his hilarious stand-up, his SNL gigs, and, of course, his incredibly high-profile relationships. It seems like everywhere Pete turns, he's linked to another incredible woman, and honestly, we're all a little bit curious, right? Today, we're going to unpack Pete Davidson's ex-girlfriends, looking at some of the most talked-about romances and what makes him such a magnet for some of Hollywood's brightest stars. It's a journey through a few years of dating headlines, and trust me, it's been a wild ride. We'll explore the timeline, the dynamics, and maybe even try to figure out what it is about Pete that captures these women's attention. So grab your popcorn, settle in, and let's get into it!

Early Romances and Rising Profile

Before Pete Davidson became a household name for his dating life, he was already making waves as a comedian. His early relationships, while perhaps less publicized, were instrumental in shaping his journey. One of the first high-profile relationships that really put his romantic life in the spotlight was with Cazzie David, daughter of comedian Larry David. They dated for about two years, from 2016 to 2018, and seemed like a pretty solid couple. Their breakup was amicable, and Pete even spoke kindly about her afterwards, showing a maturity that would become a recurring theme in how he handled public splits. It’s interesting to note how his fame grew alongside these relationships; as his profile on Saturday Night Live increased, so did the public's interest in his personal life. This period was crucial because it established a pattern: Pete, the relatable comedian, dating women who were often in the public eye, making his romances fodder for tabloids and fan speculation. It's this contrast – the down-to-earth comedian with a string of famous girlfriends – that makes his dating history so compelling. It’s not just about who he dated, but the narrative that built around it. His ability to maintain friendships and respect post-breakup, as seen with Cazzie, has often been highlighted, setting him apart from the typical celebrity drama. This early stage of his romantic journey was a proving ground, showing his capacity for genuine connection amidst the chaos of growing fame, and it laid the groundwork for the even more intense scrutiny that would follow.

The ARIANA GRANDE Era

Now, this is the one that took everyone by storm. In 2018, Pete Davidson and pop superstar Ariana Grande became one of the most talked-about couples in the world. Their whirlwind romance was insane. They started dating in May 2018, got engaged just a few weeks later in June, and even got matching tattoos. It was a classic case of love at first sight, or at least, that's how it seemed to the outside world. Pete, who had just come off his relationship with Cazzie David, seemed completely smitten, and Ariana, who had just ended her relationship with rapper Mac Miller, found solace and a new connection with the SNL comedian. Their engagement was a huge deal, plastered across every magazine and gossip site. Pete even got a portrait of Ariana tattooed on his thumb! Their relationship was a fascinating blend of public displays of affection and genuine vulnerability. Pete often incorporated aspects of their relationship into his comedy, and Ariana released songs that were seemingly inspired by him, like "Pete Davidson" on her album Sweetener. However, like many whirlwind romances, especially those under such intense public scrutiny, it couldn't last. By October 2018, just five months after getting engaged, they called it quits. The breakup was reportedly mutual and amicable, but it left fans stunned. This relationship, though brief, was monumental in defining Pete Davidson's public persona as a serial dater of A-list celebrities. It catapulted him into a new stratosphere of fame and gossip column inches. The speed and intensity of their romance, followed by the equally swift end, became a cultural moment, sparking countless memes and discussions about love, fame, and timing. It cemented his image as the guy who could capture the heart of a global pop icon, a narrative that would continue to follow him.

Bridging the Gap: Kaia Gerber and Others

Following the very public and very high-profile breakup with Ariana Grande, Pete Davidson took a brief step back from the intense celebrity dating scene, or at least, the media's focus shifted slightly. He was linked to actress Kate Beckinsale in early 2019. Their relationship, though relatively short-lived, garnered significant attention due to their age difference – Beckinsale is 20 years older than Davidson. They were photographed together at various events, including a hockey game, sparking widespread discussion about their unconventional pairing. While it didn't last, it showed Pete's continued attraction to women who were established in their careers and often older than him. This was followed by a rumored, though never officially confirmed, relationship with actress Margaret Qualley in late 2019. Then came a more significant chapter: his relationship with model Kaia Gerber. They were first linked in late 2019 and dated for a few months into early 2020. This relationship seemed more serious than some of his previous ones, with Pete accompanying Kaia to family events and showing a more settled side. Gerber’s parents, supermodel Cindy Crawford and businessman Rande Gerber, seemed to approve, which added another layer to the public perception of their relationship. Despite the apparent connection, they ultimately went their separate ways, with reports suggesting the pressures of Pete's public life and Kaia's demanding career played a role. These relationships, while not reaching the fever pitch of the Ariana Grande engagement, were crucial in showing that Pete wasn't just a flash in the pan; he was forming genuine connections, albeit ones that often struggled under the weight of public interest and demanding schedules. They demonstrated a pattern of attraction to talented, independent women, further solidifying his reputation as a man with a discerning, albeit high-profile, taste in partners.

The Kim Kardashian Phenomenon

In late 2021, the internet nearly broke when rumors began to surface linking Pete Davidson to reality TV mogul Kim Kardashian. After her highly publicized split from Kanye West, Kim made a guest appearance on Saturday Night Live, and sparks apparently flew. What started as whispers quickly escalated into full-blown dating news. They were photographed holding hands on a roller coaster, dining out, and generally appearing very much like a couple. This relationship was arguably Pete's most scrutinized to date, given Kim's global superstardom and the ongoing, often dramatic, fallout from her divorce. Their relationship brought Pete Davidson into even greater mainstream focus, positioning him alongside one of the most famous women on the planet. For months, they were a constant fixture in the tabloids, with paparazzi trailing their every move. Pete seemed to embrace the attention, even referencing Kim in his stand-up routines. The relationship appeared to be serious, with Pete even spending time with Kim's children and accompanying her to major events like the White House Correspondents' Dinner. The public fascination with their pairing was immense; it was a collision of two massive cultural figures from vastly different worlds. However, in August 2022, after about nine months together, news broke that Kim and Pete had called it quits. Sources cited the strain of their long-distance relationship and their demanding careers as primary reasons. While the breakup was reported as amicable, it once again left fans and media buzzing. The Kim Kardashian chapter solidified Pete's status as a major celebrity magnet and proved that his appeal wasn't limited to the music or comedy worlds. It was a testament to his charisma and ability to connect with women from all walks of life, regardless of their fame or background. This romance, more than any other, underscored the unique intersection of celebrity, public perception, and personal relationships in the digital age.

Beyond the Headlines: What's the Appeal?

So, guys, we've covered a lot of ground, from Cazzie David to Kim Kardashian, and it’s clear Pete Davidson has a type: successful, independent, and incredibly famous women. But what is it about Pete that draws these women to him? It’s a question that has baffled many, but when you look closer, a few things stand out. Firstly, there's his undeniable charisma and sense of humor. Pete has a way of making people laugh, and that's always an attractive quality. He's often described as being down-to-earth, genuine, and incredibly sweet, qualities that can be rare in the glitzy world of Hollywood. His vulnerability is also a key factor. Pete has been open about his struggles with mental health and his past substance abuse, and this honesty creates a sense of realness that resonates with people. Many of the women he's dated have spoken about his kindness and how he makes them feel comfortable and understood. Secondly, there's the narrative itself. Pete Davidson’s dating history has become a sort of modern-day fairy tale, albeit one with a lot of headlines. He’s the relatable guy who somehow ends up with the supermodel or the pop star. This narrative is inherently captivating. Furthermore, his public persona often downplays his own fame, making him seem more accessible and less intimidating than one might expect from someone who has been in the public eye for so long. He seems unfazed by the spotlight, often joking about the chaos surrounding his relationships, which can be disarming. While the intense media scrutiny can be a challenge, Pete has navigated it with a surprising amount of grace and humor. His ability to connect with these women on a personal level, beyond the superficialities of fame, seems to be the real secret sauce. It’s this combination of humor, vulnerability, kindness, and a genuine ability to connect that likely explains his string of high-profile relationships. He’s more than just a tabloid headline; he’s a guy who seems to genuinely value connection and isn’t afraid to show his true self, and that’s pretty darn attractive.