Pete Davidson's Dating History: A Look Back

Alright guys, let's dive into the whirlwind that is Pete Davidson's dating life. It's no secret that the SNL comedian has a knack for capturing the hearts of some seriously high-profile women. We're talking about a roster of ex-girlfriends that reads like a celebrity gossip magazine's dream. If you've ever wondered who Pete Davidson's ex-girlfriends are, or how he manages to date such an impressive lineup, you've come to the right place. We're going to break down some of his most notable relationships, exploring the timelines, the public reactions, and what made each connection so interesting. It’s a fascinating journey through modern celebrity romance, and Pete Davidson is undoubtedly one of its most captivating figures. So, buckle up, grab your popcorn, and let's get into it!

Cazzie David: The College Sweetheart

Before the massive fame and Hollywood attention, there was Cazzie David. For many, she was Pete's first serious public girlfriend, and their relationship was a significant chapter in his life. They started dating back in 2016, meeting through mutual friends. Cazzie, the daughter of comedian Larry David, was already carving out her own path in comedy and writing. Their relationship seemed genuine and down-to-earth, with plenty of adorable public moments and supportive social media posts. They were together for about two years, and it appeared to be a really loving and stable partnership. Pete often spoke fondly of her, and she was seen as a grounding force for him during a time when his career was starting to explode. However, like many relationships, especially those under the intense glare of the spotlight, it eventually ran its course. The breakup in 2018 was reported as amicable, but it was still a tough moment for both of them, especially for Pete, who was grappling with his mental health at the time. Cazzie David represented a simpler, perhaps more innocent, phase of Pete's romantic life. She was a familiar face in his orbit, and their connection felt relatable to many fans who were watching him grow from a young comedian into a household name. Her presence in his life during those formative years was undeniable, and their story serves as a reminder that even amidst the chaos of fame, personal connections and heartbreaks are a universal experience. It's clear their relationship meant a lot to Pete, and he's often credited her as someone who truly understood him during a period of rapid personal and professional transformation. The impact of their time together, though over, undoubtedly shaped his experiences and his approach to relationships moving forward.

Ariana Grande: The Whirlwind Engagement

This is arguably the most talked-about relationship in Pete Davidson's dating history, and guys, it was fast. After his split from Cazzie David, Pete quickly moved on to Ariana Grande in the spring of 2018. And when I say quick, I mean lightning quick. They met on the set of SNL and sparks flew almost immediately. Within weeks, they were Instagram official, and before anyone could even process it, they were engaged. The whirlwind romance was plastered all over the tabloids and social media. They were inseparable, sporting matching outfits, getting numerous tattoos dedicated to each other, and Pete even got a cloud tattoo on his finger that was widely believed to be inspired by Ariana's love for clouds. Their public displays of affection were intense, and their engagement was a massive pop culture moment. Fans were captivated by their seemingly passionate and spontaneous love story. Pete was head-over-heels, and he was never shy about expressing his feelings for Ariana, even dedicating segments of his stand-up to her. Ariana, too, was smitten, and her album Sweetener featured songs that many believed were about Pete. However, the intense speed of their relationship also led to its rapid demise. The pop superstar tragically lost her ex-boyfriend, Mac Miller, in September 2018, and the immense grief and pressure that followed seemed to take a toll on their relationship. Just a few months after getting engaged, in October 2018, they announced their split. It was a heartbreaking end to a romance that had captured the world's attention. The Ariana Grande chapter of Pete's life was a testament to his ability to fall hard and fast, but also a stark reminder of how quickly things can change in the public eye. It was a period of intense joy and public fascination, followed by a swift and painful dissolution that left many fans stunned. Their story remains one of the most iconic, albeit brief, celebrity romances of the late 2010s, and it certainly cemented Pete Davidson's status as a celebrity magnet.

Kate Beckinsale: The Unexpected Pairing

Following the highly public breakup with Ariana Grande, Pete Davidson surprised everyone by getting together with Kate Beckinsale in early 2019. This pairing definitely raised eyebrows, not just because of the age difference—Kate is 20 years older than Pete—but also because it was so unexpected. Kate Beckinsale, a beloved actress known for her roles in Underworld and Pearl Harbor, seemed like she was in a completely different league from the young comedian. Their relationship, however, appeared to be genuine and filled with a lot of playful PDA. They were photographed holding hands, kissing, and generally looking smitten at various sporting events and after-parties. Pete seemed particularly drawn to Kate's sharp wit and mature demeanor, while Kate seemed amused and charmed by Pete's youthful energy and unfiltered personality. They didn't shy away from the attention, and their public appearances often had a sense of defiant fun about them, as if they were enjoying defying expectations. Despite the initial shock from the public, their connection seemed to have a certain spark and chemistry. They were together for about four months, and their relationship was relatively short-lived but incredibly memorable. The reason for their split was never explicitly stated, but it's believed that the demands of their careers and the constant media scrutiny might have played a role. The Kate Beckinsale chapter proved that Pete wasn't afraid to date outside the conventional norms and that his appeal extended across different age groups and industries. It was a relationship that highlighted his evolving public persona and his willingness to embrace connections that defied easy categorization. For a brief period, they were the most talked-about unlikely couple in Hollywood, and their story remains a quirky and fascinating footnote in Pete's extensive dating history.

Margaret Qualley: A Brief but Sweet Romance

In the fall of 2019, Pete Davidson was reportedly linked to actress Margaret Qualley. This relationship was far less public than some of his previous high-profile romances, offering a breath of fresh air for those who prefer celebrity couples to keep things a bit more low-key. Margaret Qualley, known for her roles in Once Upon a Time in Hollywood and the Netflix series Maid, is a talented actress in her own right. Their rumored romance was first sparked by sightings of them together at various events, including the Venice Film Festival, where they appeared quite affectionate. Photos emerged of them holding hands and smiling, suggesting a genuine connection. Unlike some of his past relationships that were in the spotlight 24/7, the relationship with Margaret seemed to have a more private and grounded feel. They were seen enjoying each other's company without the constant pressure of tabloid headlines. This allowed their connection to develop more naturally, away from the prying eyes of the public. However, the relationship didn't last very long, reportedly ending around October 2019, after only a few months together. While the exact reasons for the split remain unclear, it's common for busy actors with demanding schedules to find it challenging to maintain relationships. The Margaret Qualley chapter, though brief, showcased Pete's continued interest in dating women within the entertainment industry and his ability to form connections that, while not always lasting, appear to be sincere. It was a sweet, albeit short, interlude in his dating life, and it demonstrated that he could also navigate romance without making it a massive public spectacle.

Kaia Gerber: The Age-Appropriate Connection?

Moving into 2020, Pete Davidson was linked to another young starlet: Kaia Gerber. The daughter of supermodel Cindy Crawford, Kaia was just 18 years old when rumors of her relationship with Pete began to circulate. This pairing, like the one with Kate Beckinsale, sparked a lot of discussion, primarily due to the age difference. However, this time, Pete was dating someone closer to his own age, which seemed to resonate differently with the public. Their relationship was relatively low-key compared to some of his more explosive romances. They were photographed together on multiple occasions, often looking comfortable and affectionate. Pete was seen supporting Kaia at events, and they appeared to be enjoying their time together. The relationship seemed to be a more mature and stable connection for Pete, perhaps benefiting from the fact that both individuals were navigating similar stages of their young careers and lives. They were seen together in various cities, including New York and Miami, and their paparazzi photos often showed them smiling and relaxed. It was a chapter that suggested Pete might be seeking a more grounded and less chaotic romantic experience. Unfortunately, like many young relationships, theirs wasn't meant to last. They reportedly broke up around January 2021, after about a year together. The reasons for the split were not widely publicized, but it's plausible that the pressures of their careers and the public's intense interest in their relationship contributed to its end. The Kaia Gerber relationship was a notable period for Pete, showing him dating someone who was a peer in terms of age and burgeoning fame, offering a glimpse into a potentially more balanced romantic dynamic before he once again entered the headlines with other high-profile relationships.

Phoebe Dynevor: A Transatlantic Affair

In the spring of 2021, Pete Davidson found himself linked to British actress Phoebe Dynevor. Known for her breakout role in the Netflix series Bridgerton, Phoebe represented another high-profile celebrity who caught Pete's eye. This relationship was particularly interesting due to its transatlantic nature, with Pete often traveling to the UK to see Phoebe, and vice versa. Their romance was initially kept quite private, but eventually, they became more comfortable with being seen together. They were photographed holding hands in London and Manchester, and Pete even attended a football match in the UK to support Phoebe. Their public appearances, though not as frequent or as intense as some of his past relationships, suggested a genuine connection and mutual affection. Pete seemed charmed by Phoebe's talent and British sensibility, while Phoebe appeared to be drawn to Pete's humor and outgoing personality. The age difference was less of a talking point this time, and the focus was more on their burgeoning romance across continents. However, like many long-distance relationships, especially those involving demanding careers, it proved to be challenging. The relationship reportedly ended around August 2021, after about six months. The demands of their respective filming schedules and the geographical distance were likely significant factors in their breakup. The Phoebe Dynevor chapter was a testament to Pete's global appeal and his willingness to pursue relationships regardless of distance. It was a period where he was again in the public eye for his romantic life, but this time with a connection that seemed to have a more mature and understanding foundation, even if it ultimately couldn't withstand the pressures of fame and distance.

Kim Kardashian: The Mega-Star Romance

And then there was Kim Kardashian. This is, without a doubt, the most high-profile relationship Pete Davidson has ever been in, and it dominated headlines for well over a year. The pair first met when Kim hosted Saturday Night Live in October 2021. Their on-screen chemistry in a comedy sketch quickly translated into off-screen sparks. What started as a seemingly casual fling quickly escalated into a full-blown romance. Kim, one of the most famous women in the world, and Pete, the lovable goofball comedian, became an iconic duo. They were photographed everywhere – cozying up on red carpets, vacationing together, and attending major events like the Met Gala. Pete even got several tattoos dedicated to Kim and her children, including initials and cartoon characters. Their relationship was a huge cultural moment, merging two massive spheres of influence: reality television royalty and comedy's resident king of relatable charm. The public was fascinated by their dynamic, with many wondering how Kim, a mogul with a sprawling empire, and Pete, a comedian still finding his footing in Hollywood, could possibly make it work. Pete was incredibly supportive of Kim's endeavors and appeared to embrace her family life, even bonding with her children. However, the intense scrutiny and the sheer magnitude of their fame inevitably took a toll. The constant media attention, the pressures from Kim's ex-husband Kanye West, and their conflicting schedules likely contributed to the strain. In August 2022, after nearly a year together, news broke that Pete and Kim had decided to go their separate ways. The breakup sent shockwaves through the entertainment world. The Kim Kardashian chapter was a period of unprecedented media frenzy for Pete, showcasing his ability to capture the attention of global superstars and navigate complex, highly publicized relationships. It was a defining moment in his career and personal life, cementing his reputation as someone who attracts and engages with the highest echelon of celebrity.

Chase Sui Wonders: The Latest Chapter?

Following his high-profile split from Kim Kardashian, Pete Davidson was reportedly seen with actress Chase Sui Wonders. The pair first sparked dating rumors in late 2022, and they were photographed together on multiple occasions throughout 2023, often looking very comfortable and affectionate. Chase Sui Wonders, known for her roles in Generation and Bodies, Bodies, Bodies (a film in which Pete also appeared), seemed like a natural fit for Pete, as she also hails from the acting world and shares a similar sense of humor. Their interactions in paparazzi photos suggested a relaxed and genuine connection, with them often seen laughing and enjoying each other's company. Unlike some of Pete's earlier, more dramatic relationships, his connection with Chase appeared to be more low-key and grounded. They were seen engaging in everyday activities, from grocery shopping to attending sporting events, giving the impression of a relationship that was developing organically away from the intense spotlight. While they haven't officially confirmed their relationship status, their consistent public appearances and displays of affection have led many to believe they are indeed a couple. This latest chapter in Pete Davidson's dating life suggests a continued pattern of him forming relationships with women within the entertainment industry, and perhaps a preference for partners who understand the unique pressures of fame. Whether this relationship is long-term or another fascinating, yet temporary, chapter remains to be seen, but it certainly keeps fans intrigued about who Pete Davidson will date next.

The Pete Davidson Phenomenon

So, there you have it, guys. A journey through some of the most notable relationships of Pete Davidson. From college sweethearts to global superstars, Pete has certainly lived a full romantic life. What is it about Pete Davidson that makes him such a magnet for these incredible women? Is it his disarming humor, his open vulnerability about mental health, or just that undeniable charm? The truth is probably a combination of everything. He’s a genuinely funny guy who doesn't seem to take himself too seriously, yet he’s also shown immense depth and sensitivity. His willingness to be open about his struggles has resonated with many, creating a unique connection that goes beyond surface-level attraction. Each of his relationships, whether brief or long-lasting, has added another layer to his public persona and has kept us all talking. The mystery of Pete Davidson's dating life continues to fascinate, and honestly, we can't wait to see what the next chapter holds. One thing's for sure: Pete Davidson's ex-girlfriends list is impressive, and his dating history is one of the most talked-about in Hollywood for today's celebrity landscape.