Pete Davidson, the comedian and actor known for his wit and charm, has become as famous for his dating life as he is for his work on screen. Often linked with successful and captivating women, Davidson’s relationships have consistently captured public attention. Among his notable romances, his whirlwind engagement and subsequent relationship with pop superstar Ariana Grande remains one of the most talked-about. So, When Did Pete Davidson Date Ariana Grande, and what led to their highly publicized, yet brief, love story?
To understand the context of Pete Davidson’s relationship with Ariana Grande, it’s worth noting his pattern of dating within the spotlight. From actresses to models and reality TV stars, Davidson’s dating history is a roll call of prominent figures. Before and after Grande, he has been linked to names like Kate Beckinsale, Kaia Gerber, Kim Kardashian, and more recently, Madelyn Cline. This consistent presence in celebrity gossip columns underscores the public fascination with his personal life.
Davidson himself has addressed the intense scrutiny surrounding his dating choices. On the Real Ones With Jon Bernthal podcast, he humorously downplayed the number of people he’s dated, stating, “In 10 years, I’ve dated 12 people … I don’t think that’s that crazy.” He also attributed his dating success to simply meeting people through work, stating, “I worked at one of the five Hollywood epicentres of where you meet people and that’s how it happened.”
Currently, Pete Davidson is reportedly dating Outer Banks star Madelyn Cline, adding another chapter to his ever-evolving dating narrative. But before Cline, and before many others, there was Ariana Grande.
Now, let’s delve into the specifics of when Pete Davidson and Ariana Grande dated and explore the timeline of their relationship within his broader dating history.
Pete Davidson’s Dating History: A Detailed Look
To fully appreciate the Pete Davidson and Ariana Grande phenomenon, let’s examine the sequence of relationships that define his romantic journey.
1. Madelyn Cline
September 2023 – Present
Most recently, Pete Davidson has been linked to Madelyn Cline, the actress known for her roles in Outer Banks and Glass Onion: A Knives Out Mystery. Rumors began circulating in September 2023 after they were spotted spending time together. Sources indicated they were keeping things casual initially, but they seemingly confirmed their relationship by attending a Saturday Night Live after-party together, where they were photographed holding hands. This relationship marks Davidson’s latest foray into the dating world following his split from Chase Sui Wonders.
2. Chase Sui Wonders
January – August 2023
Earlier in 2023, Davidson dated Chase Sui Wonders, his co-star from the film Bupkis. They were first seen together in December 2022 and their relationship progressed through early 2023, with sightings at basketball games, enjoying dates in Brooklyn, and even vacationing in Hawaii. Wonders spoke positively about their relationship to Nylon, highlighting their openness and connection. However, their relationship concluded in August 2023, with reports suggesting it had simply “run its course” without any animosity.
3. Emily Ratajkowski
November – December 2022
A brief but surprising romance blossomed between Pete Davidson and model Emily Ratajkowski in late 2022. They were seen celebrating Davidson’s birthday and enjoying each other’s company at events. Ratajkowski even hinted at the non-exclusive nature of their relationship on TikTok. However, this fling was short-lived, ending after less than two months, with sources indicating they transitioned into the “friend zone.”
4. Kim Kardashian
October 2021 – August 2022
Pete Davidson’s relationship with Kim Kardashian was arguably his most high-profile to date. It began after Kardashian hosted SNL in October 2021, where she reportedly felt a “zing” during their on-screen kiss. Their romance quickly escalated, marked by public appearances, social media buzz, and even Davidson getting tattoos dedicated to Kardashian. They attended the Met Gala together and seemed deeply invested in the relationship. Despite the intensity, the relationship ended in August 2022 after nine months, attributed to long distance and demanding schedules.
5. Phoebe Dynevor
April – August 2021
Before Kim Kardashian, Pete Davidson was romantically involved with Bridgerton actress Phoebe Dynevor. Rumors of their relationship began in early 2021, and Davidson was even spotted visiting her in England. They confirmed their relationship with public displays of affection at Wimbledon. Like many of Davidson’s relationships, this one was also impacted by distance, and they split in August 2021 after a few months together.
6. Kaia Gerber
October 2019 – January 2020
In late 2019, Pete Davidson dated model Kaia Gerber, daughter of Cindy Crawford. They were seen together in Miami, and their relationship garnered significant media attention. However, Gerber’s parents were reportedly not thrilled about the pairing. The relationship concluded in January 2020, coinciding with Davidson seeking treatment for his mental health. He later mentioned the age difference and his personal struggles as factors in the breakup.
7. Margaret Qualley
August – October 2019
Prior to Kaia Gerber, Davidson had a brief summer romance with actress Margaret Qualley in 2019. They were seen holding hands in Venice during the Venice Film Festival. Qualley’s mother, Andie MacDowell, commented positively on their relationship. However, similar to other short-lived romances, distance was cited as a reason for their split in October 2019.
8. Kate Beckinsale
January – April 2019
Following his breakup with Ariana Grande, Pete Davidson began dating actress Kate Beckinsale in early 2019. Their relationship raised eyebrows due to the 20-year age gap. They were first seen flirting at a Golden Globes after-party and later photographed kissing at a hockey game. Despite the initial spark, the intense media attention reportedly contributed to their breakup in April 2019.
9. Ariana Grande
May – October 2018
The relationship that propelled Pete Davidson’s dating life into mainstream headlines was with pop sensation Ariana Grande. Pete Davidson and Ariana Grande dated from May to October 2018. Their romance began shortly after Davidson’s split from Cazzie David and Grande’s from Mac Miller. It was a whirlwind from the start. Within weeks of dating, they announced their engagement, fueling intense media and fan frenzy. Their relationship was characterized by public displays of affection, matching tattoos, and Grande even wrote a song titled “Pete Davidson” on her album Sweetener.
However, the intense pace and public pressure took their toll. Tragically, during their engagement, Ariana Grande’s ex-boyfriend Mac Miller passed away. This event deeply impacted Grande, and Davidson was supportive during this difficult time. Ultimately, the couple called off their engagement and ended their relationship in October 2018, just five months after it began. Davidson later suggested that Mac Miller’s death was a significant factor in their breakup, understanding Grande’s need to cope with the loss.
Longest Relationship
While Pete Davidson’s relationship with Ariana Grande was highly publicized, it was not his longest. His longest known relationship was with Cazzie David, with whom he was together for two years prior to his relationship with Grande. Following Cazzie David, his longest relationship was with Kim Kardashian, lasting nine months.
Conclusion
Pete Davidson’s dating history is a subject of constant public interest, marked by a series of relationships with prominent women. While his time with Ariana Grande was brief yet impactful, lasting from May to October 2018 and culminating in a whirlwind engagement, it is just one chapter in his ongoing romantic narrative. From short flings to more significant connections, Davidson’s dating life continues to intrigue and entertain, solidifying his status as a modern-day celebrity heartthrob.
