Pete Davidson's Ex-Girlfriends: A Dating History

Let's dive into the whirlwind dating life of Pete Davidson. You know, the guy who's been linked to some of the biggest names in Hollywood? It's like, who hasn't he dated? From pop stars to actresses, Pete's relationship history is definitely something to talk about. We're going to break it all down, giving you the lowdown on each relationship, how long they lasted, and what made them so buzzworthy. So, buckle up, because this is going to be a wild ride through Pete's past romances!

Ariana Grande: The whirlwind romance and Grande Engagement

Ah, Ariana Grande, where do we even begin? This was the relationship that truly catapulted Pete Davidson into the stratosphere of celebrity dating. I mean, everyone was talking about it. It all started in the spring of 2018, and things moved fast. Like, blink-and-you'll-miss-it fast. They started dating in May, and by June, they were engaged. Seriously, it felt like they were trying to break a record for the quickest celebrity engagement ever. The world watched in fascination as they plastered their Instagram feeds with loved-up photos, gushing about each other in interviews, and generally just being all-around adorable (and a little bit nauseating, if we're being honest).

What made this relationship so captivating? Well, for starters, Ariana was at the peak of her pop stardom, and Pete was the quirky, funny guy from Saturday Night Live. It was an unexpected pairing, like mixing oil and water, but somehow, it worked—at least for a little while. They seemed genuinely smitten, and their whirlwind romance was like something out of a movie. Remember that time Pete got not one, but two Ariana-related tattoos? That's commitment, folks! Or maybe just a little bit crazy. Either way, it was clear they were head over heels for each other.

But, as we all know, the fairytale didn't last. In October 2018, just a few months after their engagement, they called it quits. The breakup came as a shock to many, especially given how public and intense their relationship had been. There were rumors and speculation, of course, but ultimately, it seemed like the pressure of fame and the intensity of their whirlwind romance had simply taken its toll. Ariana later alluded to the relationship being a rebound after her split from Mac Miller, which added another layer of complexity to the whole situation. Regardless of the reasons, the Ariana Grande-Pete Davidson saga will forever be etched in the annals of celebrity dating history. It was a wild, crazy, and ultimately short-lived chapter, but one that we won't soon forget. And let's be real, it definitely put Pete Davidson on the map as a major player in the celebrity dating game.

Kate Beckinsale: The Age-Defying Romance

After his high-profile split from Ariana Grande, Pete Davidson surprised everyone by getting cozy with Kate Beckinsale. Yes, that Kate Beckinsale. The one who seems to defy the laws of aging and looks like she stepped straight out of a movie. This relationship raised eyebrows for a couple of reasons, not least of which was the age difference. Kate is, shall we say, a bit older than Pete. But hey, age is just a number, right? And these two seemed to be having a blast together.

They were first spotted together at a Golden Globes after-party in January 2019, and the internet went wild. Pictures of them looking very cozy quickly circulated, and everyone was wondering if this was the real deal. Turns out, it was! They were seen on dates, holding hands, and generally looking like a couple in love. What was so intriguing about this pairing was how different they seemed. Kate is known for her sophisticated, elegant style, while Pete is, well, Pete. He's the king of casual, with his hoodies, sneakers, and devil-may-care attitude. But opposites attract, as they say, and these two certainly seemed to be drawn to each other.

Their relationship lasted for a few months, and they weren't shy about showing off their affection in public. There were paparazzi shots of them making out at hockey games, holding hands in New York City, and generally just enjoying each other's company. But, like many of Pete's relationships, this one eventually fizzled out. By April 2019, they had reportedly called it quits. Sources said that the distance and their busy schedules were to blame. Kate lives primarily in Los Angeles, while Pete is based in New York for SNL. Maintaining a long-distance relationship is tough, especially when you're both in the public eye. While it lasted, the Kate Beckinsale-Pete Davidson romance was definitely one for the books. It was unexpected, a little bit scandalous, and proof that love can be found in the most unlikely of places.

Margaret Qualley: A Low-Key Fling

Next up on Pete Davidson's dating roster is Margaret Qualley. This relationship was a bit more low-key compared to his romances with Ariana Grande and Kate Beckinsale. Margaret, the daughter of actress Andie MacDowell, is a talented actress in her own right, known for her roles in movies like Once Upon a Time in Hollywood and the series The Leftovers. Their relationship was first reported in August 2019, when they were spotted together in Venice, Italy. How romantic!

Unlike his previous relationships, Pete and Margaret kept things relatively private. There weren't as many paparazzi photos or gushy Instagram posts. They seemed to prefer a more low-profile approach, which is understandable given the intense scrutiny Pete had faced in his previous relationships. They were seen holding hands and looking affectionate, but they generally avoided the spotlight. This relationship felt more like a casual fling than a serious commitment. They were both young, successful, and probably just enjoying each other's company without the pressure of a long-term relationship.

By October 2019, it was reported that they had broken up. The split seemed amicable, and there was no drama involved. It simply ran its course. Some sources said that their busy schedules and different lifestyles made it difficult to maintain the relationship. Margaret was focused on her acting career, while Pete was busy with SNL and other projects. It was a brief but seemingly pleasant chapter in Pete Davidson's dating history. While it didn't last, it showed a different side of Pete – one that was capable of a more relaxed and private relationship.

Kaia Gerber: The Model Romance

In late 2019, Pete Davidson was linked to yet another famous face: Kaia Gerber. Yes, the daughter of supermodel Cindy Crawford. Talk about a pedigree! This relationship definitely turned heads, and it seemed like a match made in celebrity heaven. Kaia is a successful model, known for her striking looks and effortless style. She and Pete made a stylish couple, and their relationship was closely watched by the media.

They were first spotted together in October 2019, and they quickly became inseparable. They were seen on dates in New York City, holding hands and looking very much in love. Pete even met Kaia's parents, which is usually a sign that things are getting serious. Their relationship was characterized by a youthful energy and a sense of fun. They seemed to enjoy each other's company, and they weren't afraid to show it. However, this relationship also faced its share of challenges.

By January 2020, it was reported that they had broken up. The split was reportedly due to Pete's mental health struggles. He has been open about his battle with borderline personality disorder, and it seems that his mental health issues put a strain on the relationship. Kaia was reportedly supportive, but ultimately, it was too much for her to handle. Pete later admitted that he was not in the right place to be in a relationship at the time. The Kaia Gerber-Pete Davidson romance was a glamorous and exciting chapter, but it ultimately ended due to circumstances beyond their control. It was a reminder that even in the world of celebrity dating, mental health is a serious issue that can impact relationships.

Olivia O’Brien: The 'leaked' fling

In 2020, a rumor surfaced linking Pete Davidson to singer Olivia O'Brien. This one is a bit murky, as it's largely based on a leaked conversation and hasn't been officially confirmed by either party. According to the rumor mill, Olivia claimed that she and Pete had a brief fling before he started dating Phoebe Dynevor. The details are hazy, and it's hard to know exactly what happened. Olivia reportedly said that Pete ended things with her via text message, which, if true, isn't the most romantic way to break up with someone.

Pete's camp has denied the allegations, so it's difficult to say for sure whether or not there was any truth to the rumors. It's possible that it was just a case of miscommunication or wishful thinking on someone's part. Or maybe there was a brief encounter that never really developed into anything serious. Whatever the case, the Olivia O'Brien rumor remains a footnote in Pete Davidson's dating history. It's a reminder that not every rumored relationship is true, and that sometimes, things are more complicated than they seem.

Phoebe Dynevor: The Bridgerton Connection

In early 2021, Pete Davidson sparked dating rumors with Phoebe Dynevor, the star of the hit Netflix series Bridgerton. This was another unexpected pairing, and fans were intrigued to see what these two had in common. Phoebe is a British actress, known for her elegant style and poised demeanor. Pete, on the other hand, is, well, Pete. But opposites attract, right?

They were first linked in March 2021, when Pete was spotted in England, where Phoebe was filming Bridgerton. They were seen holding hands and looking cozy, and the internet went wild. Their relationship was characterized by a transatlantic romance, with Pete traveling back and forth between the US and the UK to see Phoebe. They seemed to be making it work, despite the distance. However, the challenges of a long-distance relationship eventually took their toll.

By August 2021, it was reported that they had broken up. The split was reportedly due to the distance and their busy schedules. Phoebe was filming in the UK, while Pete was based in New York for SNL. Maintaining a relationship across the Atlantic is tough, especially when you're both in the public eye. The Phoebe Dynevor-Pete Davidson romance was a charming and unexpected chapter, but ultimately, the distance proved to be too much to overcome. It was a reminder that even in the age of FaceTime and Zoom, long-distance relationships can be difficult to sustain.

Kim Kardashian: The ultimate power couple

And now we arrive at one of Pete Davidson's most high-profile relationships to date: Kim Kardashian. This pairing was truly a shock to the system, and it seemed to come out of nowhere. Kim, the reality TV queen and businesswoman, and Pete, the SNL comedian, seemed like an unlikely match. But somehow, they made it work—at least for a little while.

Their romance began in October 2021, after Kim hosted Saturday Night Live. They shared an on-screen kiss during a skit, and sparks apparently flew. They were soon spotted holding hands and going on dates, and the internet went into meltdown. The world watched in fascination as Kim and Pete became one of the most talked-about couples in Hollywood. Their relationship was characterized by PDA, lavish dates, and a seemingly genuine connection. Pete even got several tattoos dedicated to Kim, which is his way of showing commitment, I guess.

However, their relationship also faced its share of challenges. Kim was still dealing with her divorce from Kanye West, which created a lot of drama and tension. Pete was also subjected to online harassment from Kanye, which must have been incredibly stressful. Despite the challenges, Kim and Pete seemed determined to make it work. But in August 2022, it was reported that they had broken up. The split was reportedly due to the distance and their busy schedules. Kim is based in Los Angeles, while Pete was filming a movie in Australia. Maintaining a long-distance relationship is tough, especially when you're both juggling demanding careers and public scrutiny. The Kim Kardashian-Pete Davidson romance was a wild ride, and it proved that love can be found in the most unexpected places. But ultimately, the challenges of their relationship proved to be too much to overcome.

Chase Sui Wonders: The rebound romance

Most recently, Pete Davidson has been linked to Chase Sui Wonders. This relationship seemed to start as a rebound after his breakup with Kim Kardashian. Chase is an actress known for her roles in Generation and Bodies Bodies Bodies. She and Pete were first spotted together in December 2022, and they quickly became a regular fixture in the tabloids. Their relationship seemed to be a more low-key affair compared to his romance with Kim Kardashian.

They were seen on dates and holding hands, but they generally avoided the spotlight. Their relationship seemed to be a casual and fun distraction from the drama of his previous relationship. However, in August 2023, it was reported that they had broken up. The split was reportedly amicable, and there was no drama involved. It simply ran its course. The Chase Sui Wonders-Pete Davidson romance was a brief and relatively quiet chapter in his dating history. It was a reminder that sometimes, a rebound relationship is just what you need to move on from a previous heartbreak.

So, there you have it, a complete rundown of Pete Davidson's ex-girlfriends. It's been a wild ride, filled with unexpected pairings, whirlwind romances, and plenty of drama. Who will he date next? Only time will tell. But one thing's for sure: Pete Davidson's dating life will continue to be a source of fascination for us all.