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Pete Davidson Girlfriends: All About the Comedian’s Dating History
For years, Pete Davidson has made headlines for more than just his comedy. The Staten Island native — who first stole hearts with his offbeat humor on Saturday Night Live — has since built a reputation as one of Hollywood’s most unexpected heartthrobs. From whirlwind engagements to low-key romances, the question fans keep asking is: What is it about Pete Davidson’s girlfriends that keeps the spotlight on him?
As of August 2025, Davidson is not only preparing for fatherhood with model Elsie Hewitt but also enjoying the success of his new film The Pickup, which pairs him with Keke Palmer and Eddie Murphy. But it’s his real-life romantic history that continues to fascinate fans and tabloids alike. Here’s everything about Pete Davidson’s complete relationship timeline — from comedy clubs to red carpets to quiet getaways.
Carly Aquilino
Pete Davidson and Carly Aquilino in 2015.
Source: Instagram
In 2015, Davidson briefly dated Girl Code star Carly Aquilino. Although their relationship was brief, it left a lasting impression. Years later, when Davidson’s engagement to Ariana Grande made headlines, Aquilino couldn’t resist poking fun. Sharing a screenshot of a friend’s text, she wrote, “I can’t,” a lighthearted nod to their past. Though not a major chapter, this relationship marked the beginning of Davidson’s very public dating journey.
Cazzie David
Pete Davidson and Cazzie David ended their relationship two years after getting together.
Source: Getty Images
Davidson’s first long-term romance was with Cazzie David, daughter of comedy icon Larry David. They began dating in May 2016, and by 2018, things appeared to be solid. But just before Davidson went public with Grande, he ended things with Cazzie — a move she later opened up about in her essay collection No One Asked for This.
Davidson confirmed their breakup that same month, calling her a “very talented girl” who “will be fine.” Over time, the former couple managed to mend fences and are reportedly on friendly terms today. Their relationship, marked by its ups and downs, revealed the emotional side of Davidson that fans would come to know more intimately.
Ariana Grande
Ariana Grande and Pete Davidson.
Source: Instagram
In May 2018, just after splitting from Cazzie, Davidson began dating pop superstar Ariana Grande. The couple got engaged just weeks after going public, making them the most talked-about couple of the summer. Grande would later describe the relationship as “an amazing distraction… frivolous and fun and insane” in an interview with Vogue.
However, their engagement ended by October. The death of Mac Miller, Grande’s ex, weighed heavily on her and the relationship. Pete was left in the spotlight, dealing with public scrutiny and personal grief—he eventually covered up his Ariana-inspired tattoos and began focusing on his mental health.
Kate Beckinsale
Kate Beckinsale and Pete Davidson at a New York Rangers game at Madison Square Garden on March 3, 2019.
Source: JD Images/Shutterstock
Following his split from Grande, Davidson found comfort in British actress Kate Beckinsale. Their relationship began in early 2019 and included a now-famous courtside kiss at a New York Rangers game. Beckinsale, 20 years his senior, seemed unfazed by the age difference, but the media frenzy eventually took its toll.
“Even though Kate has been in Hollywood for a long time, she struggled with the attention,” per Page Six. The pair called it quits in April after just a few months.
Margaret Qualley
Pete Davidson and Margaret Qualley.
Source: Splash News Online
In August 2019, Pete was in Venice with actress Margaret Qualley, promoting her film, Seberg. Their romance was short-lived, ending by October, but was described by Qualley’s mother, actress Andie MacDowell, as a “beautiful relationship.” The pair went their separate ways quietly and amicably.
Kaia Gerber
Kaia Gerber and Pete Davidson.
Source: Splash News Online
Just weeks after splitting with Qualley, Davidson was spotted with Kaia Gerber, the daughter of Cindy Crawford. They dated from October 2019 to January 2020. Davidson later revealed in an interview that the relationship ended partly due to the age gap and his mental health struggles, which prompted him to seek treatment.
“She’s very young, and I’m going through a lot… it just wasn’t the right place or time,” he explained.
Did He Really Date Olivia O’Brien?
Olivia O’Brien.
Source: Instagram
Singer Olivia O’Brien claimed in 2022 that she and Davidson had a secret romance in late 2020. According to her, the comedian ended things via text. However, a rep for Davidson denied the relationship ever occurred, stating they were merely friends. Regardless of the truth, it added another name to the ever-growing list of Pete Davidson girlfriends.
Phoebe Dynevor
Phoebe Dynevor and Pete Davidson at Wimbledon in July 2021.
Source: Karwai Tang/WireImage
By March 2021, Davidson was linked to Bridgerton star Phoebe Dynevor. The two seemed smitten, with Davidson even calling her his “celebrity crush” in a Zoom call. However, by August, the long-distance aspect — with her in London and him in New York — led to their breakup just five months after they had started dating. Still, fans loved seeing this sweet pairing while it lasted.
Kim Kardashian
Kim Kardashian and Pete Davidson attend the 2022 Met Gala.
Source: Jamie McCarthy/Getty Images
Pete’s relationship with Kim Kardashian might be his most famous one yet. After sharing an onscreen kiss during a Saturday Night Live sketch where he played Aladdin opposite Kim Kardashian’s Jasmine in October 2021. Their chemistry sparked rumors offscreen, and by November, they were officially dating.
Their nine-month relationship was filled with red carpet appearances, tabloid headlines, and public drama—particularly with Kim’s ex-husband Kanye West, who repeatedly attacked Davidson on social media. Ultimately, busy schedules and life differences led to their breakup in August 2022. “Pete is totally spontaneous and impulsive… but Kim has four kids,” a source explained. It was a clash of routines, not feelings.
Emily Ratajkowski
Pete Davidson and Emily Ratajkowski at the Grizzlies vs Knicks games.
Source: Michael Simon/Shutterstock
In late 2022, Davidson was linked to model Emily Ratajkowski, just months after her divorce. The romance didn’t last long, but both parties reportedly enjoyed each other’s company. Ratajkowski had previously praised Davidson, calling him “lovely” and “vulnerable” in a 2021 interview. “Pete makes Emily laugh,” a source told Us Weekly. Though brief, their fling fed the growing curiosity about Davidson’s appeal.
Chase Sui Wonders
Chase Sui Wonders and Pete Davidson.
Source: Rosalind O’Connor/Peacock via Getty Images
From co-stars to real-life couple, Davidson and Bodies, Bodies, Bodies actress Chase Sui Wonders went public in early 2023. Their relationship seemed steady, but behind the scenes, Davidson was dealing with mental health struggles. He checked into rehab again in the summer of 2023, and the couple split in August.
“They’re both focusing on themselves,” a source shared at the time. Davidson’s openness about his journey has been a hallmark of his dating life — always candid, often vulnerable.
Madelyn Cline
Madelyn Cline at the premiere of Outer Banks season 4.
Source: Jeff Hahne
Next came Outer Banks star Madelyn Cline. Rumors began circulating in September 2023, with Cline reportedly supporting Davidson at stand-up shows and attending the SNL premiere party with him.
However, by July 2024, the relationship had run its course, despite their efforts to keep things largely private. A source described the breakup as amicable, noting the romance simply “fizzled out.”
Elsie Hewitt
Pete Davidson and girlfriend, Elsie Hewitt.
Source: Getty Images
In March 2025, Davidson was spotted in Palm Springs with model Elsie Hewitt. Unlike his previous high-profile relationships, this one felt refreshingly low-key. Hewitt, known for her Instagram presence and previous relations to stars like Ryan Phillippe and Benny Blanco, respected Davidson’s desire for privacy — and he, in turn, seemed content.
In July, Hewitt announced via Instagram that she and Davidson were expecting their first child. “Welp, now everyone knows we had sex,” she captioned a video of her ultrasound. For a man once plagued by paparazzi and chaos, fatherhood may mark a new chapter of grounding and growth.
Sources close to the couple say Hewitt has brought stability and privacy to Davidson’s life—something he openly values as he continues to manage his mental health and focus on projects he’s passionate about.
Pete and Keke Palmer’s Chemistry in The Pickup
Keke Palmer and Pete Davidson in ‘The Pickup’.
Source: Screengrab/Prime Video
Davidson’s real-life romance now echoes elements of his latest film, The Pickup (2025), where he stars alongside Eddie Murphy and Keke Palmer. The romantic comedy follows a charming yet unpredictable character who finds himself in an unexpected relationship. While the movie is fiction, some fans have noted parallels between Pete’s onscreen chemistry with Palmer and the way his real-life romances often begin—spontaneous, intense, and deeply personal.
While there’s no romance between the two stars off-camera, the movie seems to reflect Davidson’s signature vulnerability, the same qualities that have made “Pete Davidson girlfriends” a trending topic for nearly a decade.
In a recent interview, Davidson reflected on how he now prefers to keep his relationships out of the spotlight. “I just want to be known for doing good work,” he told W magazine. “I want to be seen when it’s about comedy, movies, or something meaningful—not just for who I’m dating.”
FAQs
Who is Pete Davidson dating now? As of August 2025, Pete Davidson is in a relationship with model Elsie Hewitt. The couple is expecting their first child together.
How many girlfriends has Pete Davidson had? Davidson has been linked to over a dozen high-profile women, including Ariana Grande, Kim Kardashian, Kate Beckinsale, and Phoebe Dynevor.
Did Pete Davidson date Keke Palmer? No, Davidson and Palmer starred together in the 2025 film The Pickup, but there is no evidence of a romantic relationship off-screen.
Why is Pete Davidson considered so desirable? Known for his humor, vulnerability, and emotional openness, Davidson has often been praised by former partners for being kind, funny, and deeply genuine — a rare mix in Hollywood.
