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Hollywood Life: Ariana Grande and Elsie Hewitt Spotlight

Pete Davidson’s Girlfriend History: From Ariana Grande to Elsie Hewitt
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Pete Davidson gained widespread recognition as the charismatic millennial cast member of Saturday Night Live. Over the years, he has captivated audiences with his hilarious comedy specials and memorable SNL sketches, while also receiving critical acclaim for his performances in films like The King of Staten Island. However, with this meteoric rise to fame comes intense media scrutiny, particularly regarding Pete’s romantic endeavors. From his brief engagement to the pop sensation Ariana Grande to his high-profile relationship with reality star Kim Kardashian, and his passionate flings with Kate Beckinsale, Kaia Gerber, Phoebe Dynevor, and Emily Ratajkowski, Pete has undoubtedly become one of Hollywood’s most sought-after bachelors.

As 2023 unfolded, Pete ignited a new romance with Chase Sui Wonders, his co-star from the 2022 horror-comedy film Bodies Bodies Bodies. Their relationship blossomed alongside the changing seasons, sparking excitement as it carried through the winter and well into the spring. However, on August 24, 2023, reports emerged indicating that the couple had parted ways after less than a year of dating. Soon after, he was linked romantically with Outer Banks star Madelyn Cline, stirring fresh interest in his love life.

Currently, Pete is enjoying a committed relationship with his new girlfriend, model and actress Elsie Hewitt. Their romance became public in March 2025, and shortly thereafter, Elsie shared the exciting news that she and Pete were expecting a baby together, marking a significant milestone in their relationship.

Over the years, Pete’s dating history has been a hot topic in celebrity news, with countless reports detailing his relationships. Join us as we explore the notable women who have been a part of Pete Davidson’s romantic journey throughout his career.

Revisiting the Relationship with Carly Aquilino

Pete Davidson, Carly Aquilino
Pete Davidson and Carly Aquilino dated in 2015 (AP)

Pete’s inaugural high-profile relationship took place in 2015 when he began dating fellow comedian Carly Aquilino, known for her role on MTV’s Girl Code. This was a pivotal year for Pete, as he was enjoying his second season on SNL. Although their relationship didn’t generate significant media buzz, they maintained a friendly rapport following their amicable break-up later that year. Carly even appeared in the 2020 film The King of Staten Island, which was led by Pete, and in June 2020, she expressed her gratitude via Instagram to Pete and director Judd Apatow for the opportunity to be part of the project.

Exploring the Relationship with Cazzie David

Cazzie David, Pete Davidson
Pete Davidson and Cazzie David were together for roughly two years (AP)

Following his breakup with Carly, Pete entered into a nearly two-year relationship with Cazzie David, the daughter of acclaimed comedian Larry David, who is a familiar face on SNL. Their romance began around May 2016, and in a recent interview with The Los Angeles Times, Cazzie shared that the couple was “infatuated” with each other. Despite their deep connection, she revealed that there were struggles in conveying her genuine love to him.

The couple ultimately split in early 2018, and Cazzie later expressed regret over the breakup. She attempted to reconnect with Pete, but when he finally replied, he mentioned he was “happier than he’d ever been” and ended the relationship over text. Shortly after, Pete moved on to a new high-profile romance, which Cazzie found particularly challenging to cope with.

Reflecting on their split, Cazzie described it as a pivotal moment in her life. She expressed anxiety about writing about her experiences, especially since she often spoke about her aversion to the attention that accompanied their relationship. “Why would I bring more attention to myself by writing about it? But there’s nothing that’s gonna be worse than what I already experienced with that,” she candidly shared.

Highlighting the Romance with Ariana Grande

Ariana Grande and Pete Davidson out in NYC on August 18, 2018 (MEGA)

In May 2018, Ariana Grande and Pete took their relationship public, having known each other for several years. Ariana had been a musical guest on SNL during Pete’s early tenure on the show in 2016. Their whirlwind romance escalated quickly, leading to an engagement in June 2018 after just a few weeks of dating. In a nod to their relationship, Ariana dedicated a track titled “Pete Davidson” on her album Sweetener to him. The couple frequently appeared together at red carpet events, and Pete supported Ariana at various awards shows.

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By October 2018, however, the pair ended their engagement, a breakup that occurred roughly a month after the tragic passing of Ariana’s ex-boyfriend, Mac Miller. This added an extra layer of scrutiny to Ariana as she navigated the end of her relationship with Pete. In response to the heartbreak, Ariana channeled her feelings into her music, with her 2019 album Thank U, Next featuring several references to Pete.

In the titular song “Thank U, Next,” Ariana expresses gratitude for her experiences with Pete, singing, “Even almost got married/ And for Pete I’m so thankful.” Pete, in turn, held no ill will towards his ex-fiancée, even using his time on SNL to wish her well during a segment on “Weekend Update.” He expressed, “She’s a wonderful, strong person, and I genuinely wish her all the happiness in the world,” showing maturity and respect for their shared past.

Examining the Relationship with Kate Beckinsale

Kate Beckinsale, Pete Davidson
Kate Beckinsale and Pete Davidson hold hands leaving the Motley Crue Show at The Whiskey A Go Go (BACKGRID)

The start of 2019 saw Pete embarking on a new romance with actress Kate Beckinsale, who is approximately 20 years his senior. The two were seen at various events, including a basketball game where a photo of them sharing a kiss went viral, receiving a wave of memes in the process. During their relationship, Kate shared insights in an interview with The Los Angeles Times, shedding light on their dynamic.

In March 2019, Kate remarked, “I’ve never been in this position before — never dated anybody who comes with their own bag of mischief.” She acknowledged the shocking nature of their relationship but noted that if the attraction were less intense, they might not have stayed together. Unfortunately, the couple split just a month later, in April 2019.

Unpacking the Brief Romance with Margaret Qualley

Pete Davidson, Margaret Qualley
Margaret Qualley spotted with Pete Davidson hand in hand in the streets of Venice on September 2, 2019 (MEGA)

Towards the end of the summer of 2019, Pete began dating Once Upon A Time…In Hollywood actress Margaret Qualley. In September, the couple was spotted enjoying a romantic date night in Venice. Their relationship, however, was short-lived, as they only dated for a couple of months before parting ways in October 2019.

Analyzing the Connection with Kaia Gerber

Pete Davidson, Kaia Gerber
Pete Davidson and girlfriend Kaia Gerber attended a friend’s wedding in Miami on November 23, 2019 (Mega)

Just a month after his breakup with Margaret, Pete began dating model Kaia Gerber. The couple was initially seen on a few casual outings before becoming more affectionate in public. However, their relationship was relatively brief, ending by January 2020. Despite the split, Pete held nothing but positive sentiments regarding Kaia.

In a February interview with Charlamagne tha God, Pete admitted that he was “going through a lot” before their breakup. He praised Kaia, stating, “She is beautiful, smarter than me…If anyone was worried that I was too smart or advanced for her, they do not have to worry at all. She was way, way smarter than I was,” showcasing his respect and admiration for her intelligence and character.

Investigating the Rumored Romance with Phoebe Dynevor

In early 2021, Pete Davidson once again found himself at the center of romance rumors when he was reportedly “spending time” with Bridgerton star Phoebe Dynevor in her hometown of Altrincham, Greater Manchester, on March 21. Pete was seen enjoying the local atmosphere and took photos with fans. Prior to this, Phoebe had reportedly visited Pete in Brooklyn while filming for TVLand’s Younger.

While the two did not immediately address the speculation surrounding their relationship, a local teenage girl claimed to have witnessed Pete and Phoebe “holding hands, hugging, and acting like a couple.” She noted that they appeared to be genuinely happy together, and upon approaching Pete, he humorously pretended to have an English accent, adding a playful twist to the encounter.

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In July, they were spotted sharing kisses and affectionate gestures at a Wimbledon match, but by August 2021, they had split. An insider shared with The Sun that “Pete and Phoebe’s romance was a real whirlwind,” noting the challenges posed by their busy schedules and the distance between them. Although they cared for one another, this distance ultimately proved to be too significant for their relationship to endure.

Examining the High-Profile Relationship with Kim Kardashian

Kim Kardashian and Pete captured the media’s attention when their romance blossomed. Speculation regarding their relationship began in the fall of 2021, after they were seen holding hands on a rollercoaster during a trip to Knott’s Berry Farm in Buena Park, California. Their chemistry was evident when Kim hosted Saturday Night Live that October, and they appeared to enjoy a double date with Kourtney Kardashian and Travis Barker at the amusement park.

Following their initial outings, Pete treated Kim to a private rooftop dinner in Staten Island on November 2, 2021. An insider revealed to Page Six that “Pete arranged a dinner on the rooftop privately,” emphasizing the romantic aspect of their date, which featured just the two of them.

As the months passed, the couple appeared inseparable, enjoying vacations together and displaying affection publicly. However, their relationship was short-lived, as they ended their romance after nine months of dating. Reports confirmed that the breakup occurred around the week of August 5, as a source close to Kim shared with HollywoodLife.

Detailing the Brief Affair with Emily Ratajkowski

Just months after Pete’s breakup with Kim Kardashian, reports surfaced in November 2022 indicating that Pete was dating the stunning model and actress Emily Ratajkowski. An insider disclosed to Us Weekly on November 14 that “Pete and Emily have been talking for a couple of months now.” Their budding romance was characterized as being in the early stages, with both individuals expressing genuine interest in each other. Pete’s ability to make Emily laugh and his appreciation for her intelligence contributed to their growing connection.

In July 2022, Emily ended her four-year marriage to Sebastian Bear-McClard, with whom she shares a son named Sylvester Apollo, who is now one year old. However, the couple decided to part ways in December 2022, highlighting the challenges of navigating relationships in the public eye.

Exploring the Romance with Chase Sui Wonders

Pete and Chase Sui Wonders first ignited romance rumors in December 2022 when they attended a New York Rangers game at Madison Square Garden. Speculation intensified after she was seen visiting his NYC apartment shortly after New Year’s. The two were photographed cozied up while waiting for takeout at Brooklyn’s Baba’s Perogies, clearly enjoying each other’s company.

By the end of January, the couple escaped the winter chill of NYC for a vacation in Hawaii. During this getaway, paparazzi captured images of them passionately kissing, confirming their budding romance. In another set of photos, Pete was seen sharing an affectionate moment with Chase during a tropical hike.

Their affectionate displays continued, as they were spotted kissing during a NASCAR event in Daytona. Early March saw them making out again during a second Hawaiian vacation. However, following this trip, the couple faced a harrowing incident when Pete accidentally crashed his car into a house in Beverly Hills.

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In April, Pete received the approval of lifestyle icon Martha Stewart when he and Chase visited her. Martha shared a photo on social media, captioning it: “They were out looking at our beautiful town of Bedford. I showed them around the farm and inside the winter house where the Easter Bunnies were getting ready for Sunday. Very cute couple!!!!”

Throughout his relationship with Chase Sui Wonders, Pete opened up about the challenges of having his personal life exposed to the public. “I’m in my 20s, and I’ve dated people,” he remarked on the Real Ones With Jon Berthnal podcast. “And for some reason, that’s very crazy and interesting to people. I don’t think it’s interesting.”

He further explained how the jokes about his dating life on Saturday Night Live affected him. “When it’s your own show, and I’ll be sitting in the back watching the cold open, and it’s topical political humor or whatever in the culture, and they’re making fun of you…and then you gotta walk out and do a sketch next and hit your mark…” Pete reflected on the emotional toll of being the target of jokes, expressing vulnerability about the confusing atmosphere.

Pete emphasized that he loves the people he works with, but the experience can be disorienting and psychologically taxing. “It was a really difficult thing to do,” he shared. “You feel insecure. You feel like a small person,” revealing the emotional weight he carries as a public figure.

In August 2023, just two months after entering rehab for PTSD, reports surfaced indicating that Pete and Chase had ended their relationship after less than a year. “He’s single again,” a source informed People in an August 24 report, adding, “He’s out and about and doing really well,” suggesting he is moving forward positively.

Starting Fresh with Madelyn Cline

On September 22, 2023, shortly after the news of his split from Chase, Us Weekly reported that Pete had begun a new romance with Outer Banks star Madelyn Cline. An insider shared that “Pete and Madelyn are dating,” noting they spent the night together at the Beverly Hills Hotel and enjoyed breakfast there the following morning. The source described their time together as “really low-key,” with both wearing baseball hats, indicating a desire for privacy amidst their blossoming relationship.

Just days later, People reported that Pete and Madelyn had been seen together in Las Vegas, further confirming the excitement surrounding their new romance.

Crowning the Relationship with Elsie Hewitt

In March 2025, images of Pete and Elsie surfaced online after they enjoyed a delightful beach trip in Florida. While they have kept their relationship relatively private, they made their red carpet debut as a couple in May. In July, Elsie announced the joyous news that she was pregnant, expecting her and Pete’s first child, marking an exciting new chapter in their lives.

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Sarah Parker
Sarah Parker is a research analyst and content contributor with a strong interest in business strategy, organizational behavior, and social development. With a background in sociology and public policy, she focuses on exploring the intersection between research and real-world application. Sarah regularly contributes articles that bridge academic insights and practical relevance, aiming to foster critical thinking and innovation across sectors.