Pete Davidson’s Dating Rollercoaster: A Look at Kim Kardashian and Other A-Listers in His Love Story

Pete Davidson Dating

If you’ve paid even a little attention to celebrity gossip over the past few years, you’ll know that Pete Davidson has had an epic dating life full of high highs and low lows. I’ve been fascinated by Pete’s romantic adventures, breakups, and all the drama in between. Come with me on a rollercoaster ride through his star-studded relationship history – from Ariana to Kim Kardashian and more!

First Stop: Young Love

Long before he was linked to household names, Pete had some early relationships with up-and-coming actresses and comedians. Back in 2015, he dated Carly Aquilino, an MTV Girl Code star who he met through the standup comedy scene. It seemed like a typical young Hollywood romance that ultimately fizzled out after a few months.

Next, things started getting more serious when Pete fell for Cazzie David – comedian Larry David’s daughter. They dated for over two years from 2016 to 2018, attending glitzy events arm in arm. Pete even got two tattoos dedicated to Cazzie! But this young love ran its course too. Little did we know, Pete’s rollercoaster ride was just getting started.

Engagement to Ariana Grande

In a shocking turn, Pete was quickly linked to pop superstar Ariana Grande soon after his split from Cazzie. And their relationship moved FAST! Mere weeks after they started dating, the new couple got multiple couple tattoos and Pete proposed to Ariana with a $100k ring. I remember my jaw dropping when I heard the engagement news – it seemed too good to be true!

The tabloids went wild over “Petiana,” splashing the giddy pair all over magazine covers and fueling rumors about their upcoming wedding. But sadly, this whirlwind romance came crashing down. The engagement was called off after only 5 months and both stars covered up their dedication tattoos. It was a harsh return to reality for Pete after reaching such exciting heights with Ariana.

Brief Romantic Interludes

On the rebound from his broken engagement, Pete had a string of brief dalliances with various stars to help get over the pain of his split from Ariana. First, he raised eyebrows by cozying up to Kate Beckinsale, an actress twenty years older than Pete! Their fling fizzled out after a few weeks of hand-holding at hockey games.

He moved on quickly, having a summer love affair with actress Margaret Qualley. They never officially confirmed it but were spotted cuddling around New York City. But after a tropical vacation to Italy, this relationship also dissolved. Pete closed out 2019 with a very short-term romance with model Kaia Gerber, daughter of Cindy Crawford. They were spotted holding hands but called it quits after just two months.

These whirlwind relationships showed Pete’s tendency for intense, passion-filled bonds that burn bright but fizzle quickly. It seemed he was searching for something meaningful through these romances.

Focusing Inward

In 2020, with a string of failed relationships under his belt, Pete took a step back from the dating scene to focus on his mental health and thriving comedy career. This was a mature move from Pete, showing his growth. He spoke candidly about his struggles with borderline personality disorder and past suicidal thoughts.

Pete also further cemented his star status by co-writing and starring in the semi-autobiographical movie The King of Staten Island. He had finally found stability as a Hollywood A-lister. But of course, it wouldn’t be long before Pete got back on the rollercoaster of love!

Bridgerton’s Leading Lady

In 2021, Pete was ready to test the dating waters again. This time with Phoebe Dynevor, the breakout star of Netflix hit Bridgerton. Pete fell for the glamorous British actress and they were spotted wearing matching necklaces. Fans were overjoyed to see Pete with a mature, stabilizing partner.

Unfortunately, long distance got in the way and they split after 5 months. But this relationship seemed like a turning point, with Pete describing it as “beautiful” and powered by meaningful conversations. He was clearly yearning for a deeper connection. Little did we know what – or who – was around the corner…

Kim Kardashian Changes Everything

In October 2021, rumors started bubbling that Pete was potentially dating THE Kim Kardashian. And not long after, they were spotted publicly holding hands at Knott’s Berry Farm. It was official – Pete Davidson was dating one of the most famous women in the world!

Kim and Pete’s nine-month relationship was a rollercoaster itself, full of extravagant vacations, family outings, Pete’s branded “my girl is a lawyer” merchandise, and their racy photo shoot for Kim’s shapewear line. Their mega-famous coupledom dominated headlines. Pete even got multiple Kim-inspired tattoos including her name branded on his chest.

I was totally invested in this soap opera romance between a reality icon and the comedy hunk. They seemed so in love and comfortable with each other. But of course, it couldn’t last forever. In August 2022, the couple split up amicably citing demanding work schedules.

It was the end of an era! Kimye was no more. While Pete’s time with Kim K cemented his reputation as a hopeless romantic dating the unattainable, it also showed how much he has matured and his desire for a lifelong partner.

The Rollercoaster Continues

So that brings us to today. As of late 2022, Pete Davidson is a single man again after his breakup with Kim Kardashian. His dating history reads like a tabloid fever dream! Short flings, intense connections, a failed engagement, and his zenith with a world-famous reality star.

After following his relationship ups and downs for years, I’m genuinely rooting for Pete to find happiness and stability. But I have a feeling this dating rollercoaster still has some wild turns left. We’re all waiting with bated breath to see who Pete will be linked to next!


One thing’s for sure – Pete Davidson’s love life has been a nonstop thrill ride full of drama. But underneath the tabloid gossip, I think Pete shows a sensitive heart, a longing for acceptance, and a maturity that’s grown with each relationship.

Maybe his soulmate is still out there. Could his epic dating adventures and star-studded list of exes lead him to “the one” someday? As a longtime Pete fan, I’m hoping he finally finds lasting love. But the entertainment of following his relationship rollercoaster sure has been a wild ride!

Luke is a content writer based in Los Angeles, California. He graduated from UCLA in 2018 with a degree in English and minor in Marketing. Shortly after graduating, Luke landed his first content writing role at a small LA marketing agency.

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