Who Dated Pete Davidson: A Comprehensive Timeline of His High-Profile Relationships

Pete Davidson’s romantic life has long been a subject of intense public fascination, spanning high-profile relationships with pop superstars, critically acclaimed actresses, models, and socialites. Over the years, the comedian and former Saturday Night Live cast member has been linked to numerous prominent figures in the entertainment industry, establishing a pattern of high-visibility romances that frequently dominate entertainment news cycles.

Introduction to Pete Davidson's Dating History

The public fixation on who Pete Davidson has dated stems from a combination of his meteoric rise in comedy, his distinct personal style, and his frequent association with some of the most famous women in the world. While some relationships were brief, high-intensity public pairings, others lasted for longer stretches or remained relatively low-key. Understanding his dating history requires examining the chronological progression of his public relationships, the context surrounding each pairing, and the cultural fascination that follows his romantic life.

Early Career and First High-Profile Relationship: Cazzie David

Before becoming a household name across global tabloid media, Pete Davidson’s most prominent early relationship was with writer and actress Cazzie David, daughter of comedian Larry David.

The Dynamics of the Relationship

Davidson and David began dating in 2016 and were together for roughly two and a half years. During this period, Davidson was establishing his footing as a breakout cast member on Saturday Night Live. The couple frequently shared glimpses of their relationship on social media, presenting a relatively grounded image compared to his later relationships.

The Breakup and Aftermath

The couple parted ways in May 2018. The split gained renewed public attention later when David released her collection of essays, No One Asked for This, in which she candidly discussed the emotional aftermath of the breakup and Davidson's rapid transition into his next major relationship.

The Whirlwind Engagement: Ariana Grande

The most seismic shift in Pete Davidson's public profile occurred in the summer of 2018, when he began dating pop superstar Ariana Grande. This relationship transformed Davidson from a recognizable comedic actor into a primary fixture of global celebrity gossip.

Timeline of the Romance

• May 2018: Reports emerge that Davidson and Grande are dating, shortly after both end previous long-term relationships.
• June 2018: Davidson confirms they are engaged after a whirlwind romance of just a few weeks, accompanied by matching tattoos and a move into a luxury New York City apartment.
• October 2018: The engagement is officially called off, and the couple separates amicably amid personal challenges and shifting circumstances.

Cultural Impact

The relationship introduced Davidson to a new level of intense media scrutiny. Grande’s subsequent studio album, Thank U, Next, heavily referenced Davidson, cementing the romance in modern pop culture history. Despite the rapid end of the engagement, both parties consistently spoke of each other with mutual respect in later interviews.

Post-Grande Romances: Kate Beckinsale and Margaret Qualley

Following his high-profile split from Grande, Davidson experienced a series of shorter, highly scrutinized relationships with notable film and television actresses.

Kate Beckinsale

In early 2019, Davidson was linked to British actress Kate Beckinsale. The pair first sparked dating rumors at a Golden Globes afterparty and were later spotted publicly at a New York Rangers hockey game, where their affectionate displays drew massive media attention. The relationship lasted for a few months before concluding amicably in the spring of 2019.

Margaret Qualley

Later in 2019, Davidson entered a brief relationship with actress Margaret Qualley, daughter of Andie MacDowell. The couple was spotted together at the Venice Film Festival, where Qualley was promoting a film project. This romance was notably more private than his previous pairings and concluded after a few months.

High-Profile Relationships of 2020 to 2022

As Davidson's career expanded into feature films, including The King of Staten Island, his dating life continued to capture headlines through associations with supermodels and reality television icons.

Kaia Gerber

In late 2019 and early 2020, Davidson dated model Kaia Gerber, daughter of Cindy Crawford. The relationship drew significant attention from fashion and lifestyle media. Davidson later spoke publicly about how Gerber supported him during personal health struggles, noting that the relationship ultimately ended because he required time and space to focus on his well-being.

Phoebe Dynevor

In early 2021, romance rumors linked Davidson with Bridgerton star Phoebe Dynevor. The transatlantic relationship involved travel between the United Kingdom and the United States, but the demanding production schedules of both actors ultimately led to a mutual decision to part ways later that year.

Kim Kardashian

In late 2021, Davidson began dating reality television star and entrepreneur Kim Kardashian. The relationship developed rapidly following Kardashian’s hosting stint on Saturday Night Live, where the two shared an onscreen comedic kiss.

• Duration: Approximately nine months, from late 2021 to August 2022.
• Media Reception: The pairing generated unprecedented tabloid coverage, frequently referred to by media outlets as a defining pop-culture crossover of the era.
• Conclusion: The couple separated due to demanding long-distance work schedules and contrasting lifestyles, remaining on amicable terms.

Recent Romances: Emily Ratajkowski, Chase Sui Wonders, and Madelyn Cline

In the period following his relationship with Kardashian, Davidson maintained a consistent presence in entertainment news with several subsequent relationships.

Emily Ratajkowski

In late 2022, Davidson was briefly linked to model and author Emily Ratajkowski. The romance generated significant interest across lifestyle publications before transitioning into a platonic friendship after a few weeks of public dates.

Chase Sui Wonders

While starring in the thriller comedy film Bodies Bodies Bodies and the television series Bupkis, Davidson began dating co-star Chase Sui Wonders. The relationship lasted for several months through late 2022 and early 2023, characterized by low-key public appearances in New York City before concluding amicably.

Madelyn Cline

In late 2023, reports connected Davidson with actress Madelyn Cline, known for her role in Netflix’s Outer Banks. The pair were spotted at various public events and entertainment venues, maintaining a relatively low profile regarding their personal lives before parting ways in 2024.

Frequently Asked Questions

Who was Pete Davidson’s most famous girlfriend?

While fame is subjective, his engagement to pop superstar Ariana Grande in 2018 and his relationship with media mogul Kim Kardashian in 2021–2022 generated the highest volume of global media attention and public interest.

Were Pete Davidson and Ariana Grande engaged?

Yes. Davidson and Grande became engaged in June 2018 after dating for a few weeks. The engagement was called off in October 2018, and both parties went their separate ways.

How long did Pete Davidson and Kim Kardashian date?

Pete Davidson and Kim Kardashian dated for approximately nine months, beginning in late 2021 and concluding in August 2022, citing busy schedules and distance as primary factors in their amicable split.

Why does Pete Davidson’s dating life receive so much media attention?

Davidson’s relationships frequently involve high-profile icons across music, fashion, and film. Combined with his high-visibility career in comedy and television, his romantic pairings naturally attract substantial coverage from entertainment journalists and the public.

Conclusion and Final Observations

Pete Davidson’s dating history reflects a diverse cross-section of modern celebrity culture, ranging from early industry relationships to global-scale romances with some of the most recognizable figures in entertainment. While public fascination with his personal life remains high, his ability to maintain amicable relationships with many of his former partners highlights a consistent pattern of mutual respect amidst intense media scrutiny.