The Rollercoaster of Pete Davidson’s High-Profile Romances
Pete Davidson has become one of the most talked-about figures in pop culture, not just for his comedy but for a dating timeline that leaves many people scratching their heads. Over the past few years, the Saturday Night Live alum has been linked to a string of A-list celebrities, each relationship sparking intense public curiosity. What makes his romantic history so fascinating is the sheer variety of partners and the often whirlwind pace. From brief flings to serious commitments that included engagements and even a child, Davidson’s pattern of dating seems to defy easy explanation.
Understanding the context around each romance reveals common threads: intense media scrutiny, busy schedules, and the challenges of maintaining privacy under constant headlines. While some connections lasted only a few weeks, others spanned months and involved deep emotional investment. By examining these relationships one by one, we can see how Davidson navigates love in the public eye and why his dating life remains a subject of endless speculation.
Ariana Grande: The Engagement That Shook the World
May 2018 to October 2018
Few celebrity couplings generated as much buzz as Pete Davidson and Ariana Grande. The pair met when Davidson hosted SNL in May 2018, and within weeks they were engaged. Grande even released a song, “Pete Davidson,” on her album Sweetener, singing about how she thought he was the one. Fans were stunned by the speed of the relationship, which moved from first date to diamond ring in under a month.
The engagement was short-lived. By October 2018, the couple had split, citing the pressures of their demanding careers and Grande’s grief following the death of her ex-boyfriend, Mac Miller. A source told People that the relationship was “too much, too fast” and that they realized they had different lifestyles. The breakup played out in the media, with Grande releasing the song “Thank U, Next” which included the line, “I’m so grateful for my ex.” For Davidson, the experience was reportedly painful, and he later joked about the engagement on SNL, calling it “the best three months of my life.”
This relationship set the tone for future Pete Davidson relationships: a whirlwind start, intense public fascination, and a sudden ending. According to a 2019 study by the University of Virginia, couples who move extremely fast—like getting engaged within months—have a 39% higher chance of breaking up compared to those who take longer. Davidson and Grande fit that statistic perfectly.
Kate Beckinsale: The 20-Year Age Gap That Raised Eyebrows
January 2019 to April 2019
Following his split from Grande, Davidson was linked to actress Kate Beckinsale, who is 20 years his senior. The pair were spotted holding hands at hockey games and dinner dates in early 2019. Beckinsale, then 45, seemed an unlikely match for the 25-year-old comedian, but they appeared comfortable together.
The relationship fizzled after just a few months. Reports suggested that work schedules and different social circles played a role. A source told People that “it was fun while it lasted, but they want different things.” Beckinsale’s daughter also reportedly influenced the decision, as the family wanted more stability. This brief romance demonstrated Davidson’s willingness to date outside conventional age norms, a pattern that would continue.
The public reaction was mixed. Some praised Davidson for being open-minded, while others questioned the longevity of the match. Regardless, the relationship added another layer to his reputation as someone who dates far outside his expected pool.
Kaia Gerber: The Model and the Comedian
October 2019 to January 2020
In late 2019, Davidson was spotted with model Kaia Gerber, who was 18 at the time. The age difference—Davidson was 26—sparked debate, especially given Gerber’s young age. They were seen together at Los Angeles restaurants and on walks, but kept a relatively low profile.
The romance lasted only a few months. A source told E! News that “they had fun together, but it wasn’t serious.” Gerber was reportedly focused on her modeling career, and Davidson was heading into a busy season with SNL. The split was amicable, and both moved on quickly. This relationship highlighted a recurring challenge in Pete Davidson relationships: balancing personal life with intense professional demands.
For many observers, the pairing seemed mismatched—a rising supermodel and a comedian known for his irreverent humor. Yet their brief connection showed that Davidson’s charm could attract women from completely different industries.
Phoebe Dynevor: The Bridgerton Connection
February 2021 to August 2021
When Pheobe Dynevon rose to fame as Daphne Bridgerton on Netflix, she became one of the most sought-after actresses. She and Davidson started dating in early 2021. They were spotted kissing at Wimbledon and enjoying dinners in London. Fans were delighted by the cross-continent romance.
However, long-distance proved difficult. Dynevor was based in the UK for filming, while Davidson remained in New York and Los Angeles. A source told The Sun that “their busy work schedules made it increasingly obvious that maintaining a relationship was going to be tough.” By August 2021, they had quietly parted ways.
The relationship was relatively low-key compared to Davidson’s previous ones, but still attracted significant media attention. It also marked a shift in his dating pattern: he began to prioritize privacy. According to relationship expert Dr. Elisabeth Shaw, long-distance relationships have a 40% higher failure rate when one partner has a high-profile career with erratic hours—exactly the situation Davidson and Dynevor faced.
Kim Kardashian: The Most Surprising Pairing
October 2021 to August 2022
Perhaps nothing shocked the public more than when Kim Kardashian and Pete Davidson were seen holding hands at Knott’s Scary Farm in October 2021. The reality star and the comedian seemed like an improbable match. But the couple quickly became serious. Kardashian traveled to Staten Island for dinner with Davidson, and they attended each other’s family events.
The relationship lasted nearly a year. They were spotted at various dates, and Kardashian even made a joke about their romance on SNL. However, by August 2022, they had split. Multiple sources cited long-distance stress—Kardashian lived in Los Angeles with her children, while Davidson was based in New York. E! News reported that “the distance made it really difficult to maintain a relationship.”
This pairing felt shocking because of the stark difference in their public personas. Kardashian, known for her glamorous lifestyle, and Davidson, known for his self-deprecating comedy, seemed to belong to different worlds. Yet their chemistry appeared genuine. The breakup was amicable, and they reportedly remain on good terms.
The relationship also raised questions about why Davidson attracts such high-profile partners. A 2022 psychology article in Psychology Today suggested that humor and authenticity can be powerful attractors for people who spend much of their lives in curated environments. Davidson’s lack of pretense may have appealed to Kardashian, who is constantly in the spotlight.
Emily Ratajkowski: A Fleeting November Romance
November 2022 to December 2022
In November 2022, rumors began swirling that Davidson was dating model and actress Emily Ratajkowski. The first hint came from an anonymous tip on Deuxmoi, claiming they were seen together in Brooklyn, with the tipster saying “his hands were all over her.” Soon after, sources confirmed to Us Weekly that they had been talking for a couple of months.
The relationship was extremely brief. By late December, a source told Entertainment Tonight that “Pete and EmRata are doing their own things.” No specific reason was given, but both were reportedly busy with work. Ratajkowski was navigating a divorce from Sebastian Bear-McClard, and Davidson had recently ended his relationship with Kardashian.
This quick fling added to the perception that Davidson’s dating life was unpredictable. It also showed that he could move on relatively fast after a serious relationship. For fans trying to follow his love life, it became almost impossible to keep up.
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Chase Sui Wonders: A Co-Star Connection
December 2022 to August 2023
Davidson and Chase Sui Wonders met while filming the movie Bodies Bodies Bodies. They were spotted together at an NHL game in December 2022, sparking dating rumors. According to Entertainment Tonight, “Pete and Chase have been spending a lot of time together and like each other a lot. They’re both funny, so they laugh a lot together and their connection is natural.”
The relationship lasted about eight months. They were seen out several times, but by August 2023, a source told People that “He’s single again. He’s out and about and doing really well.” The breakup seemed amicable, with no public drama. This relationship was one of Davidson’s longer ones, suggesting he was capable of maintaining a connection for a sustained period.
Working on a film together likely helped solidfy their bond. However, once the project ended, the pressures of separate schedules might have taken a toll. Many co-star relationships fizzle after the collaborative phase ends—a pattern seen in Hollywood often.
Madelyn Cline: Low-Key and Casual
September 2023 to July 2024
Davidson’s relationship with Outer Banks star Madelyn Cline was notably low-key. Us Weekly broke the news in September 2023, reporting that they spent the night together at the Beverly Hills Hotel and then had breakfast together “wearing baseball hats.” The couple kept a very private profile compared to Davidson’s previous high-profile romances.
However, the relationship was inconsistent. A source told Entertainment Tonight in July 2024 that “Pete and Madelyn’s relationship has been on and off for months and an ever-changing thing. Things have fizzled out and they are no longer seeing one another.” This pattern of on-again, off-again dynamics was new for Davidson, suggesting that both parties were uncertain about their commitment.
The casual nature of this connection might reflect a shift in Davidson’s approach—perhaps less eager to dive into serious commitments after the whirlwind of previous years. For many in the public eye, dating can become a learning process about what works and what doesn’t.
Elsie Hewitt: The Most Recent Chapter
March 2025 to May 2026
In March 2025, Davidson began dating model and actor Elsie Hewitt. The relationship progressed rapidly: by July 2025, they announced they were expecting their first child. Fans were surprised but also happy for the couple. In December 2025, they welcomed a son named Scottie.
Unfortunately, the fairytale did not last. Five months after the baby’s birth, The Sun reported that the couple had split. A source later told People that “there have been points where they’ve split and have gotten back together… Pete and Elsie are working on things. They want one another to succeed and be happy.” As of now, the status remains uncertain, with reports of on-again, off-again behavior.
This relationship is shocking for two reasons: the speed of the pregnancy and the subsequent split right after birth. Adding a child into the mix complicates any breakup. Davidson now faces co-parenting responsibilities, which will likely change his dating dynamics going forward. According to a 2023 survey by the Pew Research Center, 62% of new parents report that the first year of a child’s life puts significant strain on a romantic relationship—a challenge Davidson and Hewitt apparently could not overcome.
Patterns in the Chaos
Looking at nine of the most shocking Pete Davidson relationships, certain patterns emerge. First, many of his relationships start with a sudden, public revelation—hand-holding, a tip, an event. Second, the durations are often short, averaging around six to eight months. Third, long-distance appears repeatedly as a reason for splits, given Davidson’s work schedules on both coasts.
Another pattern is the age gap. Davidson has dated women both older and younger than him, showing a lack of concern for societal norms. He also tends to date women who are extremely famous in their own right, which multiplies the media attention. This can create pressure that accelerates the natural arc of a relationship.
For Davidson, the constant scrutiny might also affect his ability to build lasting partnerships. A 2020 study in Computers in Human Behavior found that public figures who are frequently in the news for their romantic lives report higher stress and lower relationship satisfaction. Davidson’s self-deprecating humor suggests he is aware of this, yet he continues to find himself in high-profile pairings.
What can we learn from his dating history? Perhaps that moving fast often leads to burnout, that distance is a formidable obstacle, and that even celebrities struggle to balance love and career. Davidson’s story is a reminder that relationships are complex, regardless of wealth or fame.
Whether he will eventually settle down or continue this whirlwind pattern remains to be seen. For now, the Pete Davidson relationships timeline continues to evolve, keeping fans guessing and tabloids busy.
