Few celebrities have captured the public’s fascination with their romantic entanglements quite like Pete Davidson. The Saturday Night Live alum turned Hollywood A-lister has dated some of the most iconic women in entertainment, each relationship becoming a media frenzy that transcends typical tabloid fodder. His dating history isn’t just a list of exes—it’s a reflection of modern celebrity culture, mental health discourses, and the blurred lines between personal life and public spectacle.
From his whirlwind engagement to Ariana Grande to his brief but explosive fling with Kim Kardashian, Davidson’s relationships have been dissected, memed, and analyzed to an extent rarely seen in pop culture. This article breaks down every confirmed romance in his dating timeline, complete with:
- Detailed timelines with key dates and milestones
- Cultural impact of each relationship (memes, music, and media coverage)
- Behind-the-scenes insights from interviews and sources
- How each romance shaped Davidson’s career and public persona
Whether you’re a longtime fan or just curious about the hype, this is the definitive guide to Pete Davidson’s love life.
Early Relationships: Before the Fame (Pre-2016)
Before Davidson became a household name, his dating life was relatively low-key. These early relationships laid the groundwork for his later, more public romances.
1. Carly Aquilino (2014–2015)
Who she is: A comedian and cast member on MTV’s Girl Code, Aquilino was one of Davidson’s first serious relationships in the public eye.
Timeline:
- 2014: The couple starts dating after meeting through New York’s comedy scene.
- 2015: They break up amicably, with Aquilino later joking about their relationship in her stand-up routines.
Why it matters: This was Davidson’s first brush with dating someone also in the entertainment industry, setting a pattern for his future relationships. Aquilino’s comedy often referenced their time together, giving fans early glimpses into Davidson’s humor and vulnerability.
2. Kaia Gerber (Rumored, 2016)
Who she is: The daughter of supermodel Cindy Crawford, Gerber was just 15 at the time of the rumors (Davidson was 22), which led to significant backlash.
Timeline:
- 2016: Paparazzi photos surface of Davidson and Gerber at a party, sparking speculation.
- Immediate aftermath: Both parties denied any romantic involvement, with Davidson later calling the rumors "gross" in interviews.
Cultural impact: This was Davidson’s first experience with cancel culture. The age gap controversy forced him to address the situation publicly, marking a turning point in how he handled media scrutiny.
The Ariana Grande Era: A Whirlwind Engagement and Public Scrutiny (2018)
No relationship defined Davidson’s early fame more than his engagement to Ariana Grande. Lasting just four months, their romance was a masterclass in celebrity love—intense, public, and ultimately explosive.
Timeline of Their Relationship
- May 2018: Davidson and Grande meet on the set of SNL, where she was performing. They bond over their shared love of comedy and music.
- May 20, 2018: They’re spotted holding hands in NYC, confirming their relationship.
- June 11, 2018: After just three weeks of dating, Davidson proposes with a $93,000 diamond ring. Grande shares the news on Instagram with the caption, “I said yes.”
- July 2018: The couple gets matching tattoos (a cloud and lightning bolt, respectively) and moves in together in a $16M NYC apartment.
- October 14, 2018: Grande calls off the engagement following the death of her ex, Mac Miller, and personal struggles. They announce their split but remain on good terms.
Why This Relationship Was a Cultural Moment
1. The Speed of Their Romance
Their engagement after three weeks shocked fans and media alike. Psychologists and relationship experts weighed in, with some calling it a "trauma bond" (both had recently ended long-term relationships—Davidson with Cazzie David, Grande with Mac Miller).
2. Music and Pop Culture References
Grande’s album Sweetener (released August 2018) included tracks like “Pete Davidson” and “Better Off,” which fans dissected for clues about their relationship. Later, her 2019 hit “thank u, next” referenced Davidson with the line, “Even almost got married / And for Pete, I’m so thankful.”
3. Mental Health Discussions
Davidson opened up about his borderline personality disorder (BPD) diagnosis during this time, crediting Grande with encouraging him to seek help. Their breakup led to a highly publicized mental health crisis for Davidson, including a suicide scare in December 2018.
4. The Memes and Backlash
Davidson faced relentless online harassment from Grande’s fanbase, with critics blaming him for the failed engagement. Memes like “Pete Davidson’s tattoo artist” (referencing his many ink tributes to Grande) went viral.
Post-Ariana: Rebound Romances and Self-Discovery (2019–2020)
After the Grande split, Davidson’s dating life became a mix of high-profile flings and introspective growth. This period was marked by short-lived romances and a shift in his public image.
1. Kate Beckinsale (January–April 2019)
Who she is: The Underworld actress, 20 years Davidson’s senior, became his first post-Ariana romance.
Timeline:
- January 2019: Spotted kissing at a hockey game. The 20-year age gap dominated headlines.
- April 2019: They split amicably, with Beckinsale later calling Davidson “one of the kindest, funniest people” she’s met.
Cultural impact: This relationship challenged ageist double standards in Hollywood. While some praised their chemistry, others criticized Beckinsale for dating someone so much younger.
2. Margaret Qualley (August–October 2019)
Who she is: The Once Upon a Time in Hollywood actress and daughter of Andie MacDowell.
Timeline:
- August 2019: They’re seen holding hands in NYC.
- October 2019: Split due to conflicting schedules (Qualley was filming Maid in Canada).
Why it mattered: This was Davidson’s first low-drama relationship post-Ariana, signaling a shift toward more private romances.
3. Cazzie David (Reconciliation Attempt, 2020)
Who she is: Davidson’s ex-fiancée (pre-Ariana) and daughter of Larry David.
Timeline:
- Early 2020: Rumors swirl of a reconciliation after they’re spotted together.
- March 2020: Davidson confirms they’re “just friends” on SNL.
Significance: This period showed Davidson’s attempt to reconnect with his past before moving forward.
Phoebe Dynevor: A Transatlantic Romance (2021–2022)
Davidson’s relationship with Phoebe Dynevor (star of Bridgerton) marked his first serious romance since Ariana Grande. Their transatlantic love story was charming but ultimately short-lived.
Timeline
- March 2021: They’re first linked after meeting on the set of SNL (where Dynevor was a host).
- April 2021: Confirm their relationship with a PDA-filled trip to Disneyland.
- August 2021: Move in together in Brooklyn, with Dynevor often spotted at Davidson’s stand-up shows.
- April 2022: Split due to distance and career demands (Dynevor was filming in the UK).
Why Fans Loved Them
1. Low-Drama Dynamic
Unlike his past relationships, Davidson and Dynevor kept their romance relatively private, with minimal tabloid drama.
2. Cultural Exchange
Fans loved their British-American dynamic, with Dynevor introducing Davidson to UK culture (including football—soccer—matches).
3. Career Synergy
Both were rising stars—Davidson in Hollywood, Dynevor in streaming. Their relationship boosted each other’s profiles without overshadowing their work.
The Breakup: What Went Wrong?
Sources cited logistical challenges (Dynevor’s filming schedule in the UK) and Davidson’s reluctance to leave New York. Unlike his past splits, this one remained civil, with no public feuds.
Kim Kardashian: The Most Scrutinized Fling of His Career (2022)
When Davidson started dating Kim Kardashian in October 2021, the internet broke. Their nine-month romance was a media circus, blending reality TV, memes, and high-fashion moments.
Timeline
- October 2021: They’re spotted holding hands at a Halloween party (Kardashian as Scream’s Ghostface, Davidson as a E.T. lookalike).
- November 2021: Their first public date at a Knicks game goes viral.
- December 2021: Kardashian appears on SNL with Davidson, solidifying their relationship in pop culture.
- March 2022: They attend the Met Gala together, with Davidson’s “Kim’s bf” tattoo (later covered up) making headlines.
- August 2022: They split after nine months, with sources citing Kardashian’s busy schedule and Davidson’s desire for a low-key life.
Cultural Impact: Why This Relationship Was Different
1. The Kanye West Factor
Kardashian’s ex-husband, Kanye West, publicly harassed Davidson for months, releasing diss tracks (“Eazy”) and threatening him on social media. This added a layer of danger and toxicity to their romance.
2. Reality TV vs. Real Life
Their relationship played out on Keeping Up with the Kardashians and The Kardashians (Hulu), blurring the line between authentic love and performative romance.
3. Fashion and Memes
Davidson’s streetwear-meets-high-fashion style (often in Kardashian’s designer fits) became a meme. His “Kim’s bf” tattoo and “I’m dating Pete Davidson” merch sold out instantly.
4. The Age Gap Debate
With a 13-year age difference, their relationship reignited discussions about power dynamics in celebrity couples.
Aftermath: How It Changed Davidson
Post-split, Davidson:
- Took a social media break (deleting Instagram).
- Starred in Bodies Bodies Bodies and The King of Staten Island, using humor to process his fame.
- Spoke openly about the pressure of dating in the public eye in interviews.
Pete Davidson’s Dating Life in 2024: Where Does He Stand Now?
As of 2024, Davidson appears to be single and focused on his career, but rumors continue to swirl. Here’s what we know:
Rumored Flings (2023–2024)
- Emily Ratajkowski (2023): Spotted together at a Knicks game, but both denied dating rumors.
- Chase Sui Wonders (2023): His Bodies Bodies Bodies co-star fueled speculation after they were seen together in NYC.
- Madison Beer (2024): Fans shipped them after they followed each other on Instagram, but nothing was confirmed.
Has Pete Davidson Changed His Approach to Dating?
In recent interviews, Davidson has hinted at:
- Prioritizing privacy: “I don’t want my relationships to be a spectacle anymore.”
- Therapy and growth: He’s spoken about working on his attachment issues post-Kardashian.
- Career focus: With roles in
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