Pete Davidson’s Relationships History: From Comedians to Pop Stars and Models

Pete Davidson, the charismatic comedian known for his tenure on “Saturday Night Live,” has had a dating history as eventful as his comedy career. From brief flings to headline-making engagements, Davidson’s love life has captured the public’s imagination. Here’s a glimpse into the relationships that have played out in the limelight.

Early Life and Career Beginnings

Pete Davidson’s life story is one marked by personal tragedy and professional triumph. Born on November 16, 1993, in Staten Island, New York, Davidson faced the devastating loss of his father, a firefighter, during the September 11 attacks. This event profoundly influenced his mental health and later his comedic material. Despite these challenges, Davidson found solace in stand-up comedy, starting at the tender age of 16.

Breakthrough and Rise to Fame

Davidson’s big break came when he joined the cast of “Saturday Night Live” in 2014, becoming one of the youngest cast members ever. His brand of humor, often delving into his personal life and mental health struggles, quickly made him a standout on the show.

The Comedic Connection: Carly Aquilino

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Davidson’s foray into romance began with fellow comedian and actress Carly Aquilino in 2015. Their split appeared amicable, and they subsequently shared the screen in the 2020 movie “The King of Staten Island.” Carly expressed her gratitude to Pete for the opportunity by posting a public thank you on Instagram regarding her role in the film. While the relationship didn’t last long, it set the tone for Davidson’s future star-studded love life.

A Serious Note with Cazzie David

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

In a more serious turn, Davidson dated Cazzie David, daughter of comedian Larry David, from 2016 to 2018. Their relationship was a significant chapter in Davidson’s life, with both parties openly discussing the mental health struggles they faced together and apart. All didn’t go well in their relationship, in fact, Cazzie David wrote in her essay collection that she felt attacked when Pete Davidson moved on the day after he ended their relationship in 2018.

The Whirlwind Engagement: Ariana Grande

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Perhaps Davidson’s most headline-grabbing relationship was with singer Ariana Grande. The couple’s quick engagement in 2018, just weeks after they started dating, shocked fans and media alike. However, their love story was short-lived and ended in just four months. News of their split came a little over a month after Grande’s ex Mac Miller, whom she dated prior to Davidson, died of an accidental overdose.

Age-Defying Romance: Kate Beckinsale

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

After his split from Grande, Davidson was linked to actress Kate Beckinsale, despite a 20-year age gap. Their public displays of affection, including a memorable outing at a New York Rangers game, were a bold statement post-breakup. In an interview with LA Times, describing her relationship with Pete, Kate said, “I’ve never been in this position before — never dated anybody who comes with their own bag of mischief,” she said. “It’s all quite shocking, and something to get used to.”

Summer Love: Margaret Qualley

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Davidson’s summer romance with actress Margaret Qualley in 2019 was a brief but sweet affair, confirmed by sightings of the couple in Venice, Italy. In August 2019, Pete was seen sitting behind Margaret at the Venice Film Festival premiere of her movie Seberg and in September they were spotted holding hands and strolling around Venice. In October 2019,  Us Weekly reported the former couple split after a “whirlwind romance”.

Runway Romance: Kaia Gerber

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Later in 2019, Davidson found love with model Kaia Gerber who is the daughter of Cindy Crawford. The couple were first linked in October when they were spotted on a lunch date in the SoHo neighborhood of New York City. Us Weekly broke the news of their relationship later that month. The relationship was intense but went toast as Davidson checked into rehab, citing mental health concerns.

The Secret Fling: Olivia O’Brien

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Singer Olivia O’Brien claimed to have had a fling with Davidson in 2020, which he denied, stating they were just friends. Pete’s rep said that they were friends and hung out a few times. Olivia had alleged that Davidson broke things off via text message. “He texted me and was like, ‘I’m seeing someone else,’” she recalled. “‘So, like, I can’t.’”

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Across the Pond: Phoebe Dynevor

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

In 2021, Davidson’s romance with “Bridgerton” star Phoebe Dynevor made waves as he crossed the Atlantic to spend time with her in the UK. Davidson first ignited speculation about a romantic connection with Dynevor, 27, when they were spotted together in the U.K. in March 2021. The following month, it was confirmed by US magazine that the two were in an official relationship. At that point, an insider exclusively shared details on how the couple was managing their long-distance relationship. However, the distance proved too much, and the relationship ended.

A Roller Coaster of Love: Kim Kardashian

Kim Kardashian

Davidson’s most recent high-profile relationship was with reality star Kim Kardashian. The 41-year-old founder of SKIMS, discussed her emotions for the 28-year-old “Saturday Night Live” star during the June 9 episode of Hulu’s “The Kardashians.” Confronted by a producer about whether she was in love, Kim seemed momentarily taken aback before she playfully retorted, “I’m not sure that’s something for you to know.”

In the June 2 installment of “The Kardashians,” Kim recounted how her interest in Pete was piqued following their on-screen kiss in an “SNL” sketch. “There was just a vibe when we kissed during the scene,” she reflected. “I thought, ‘Oh shit, maybe I’ve been… perhaps I should consider trying something new.'”

PEOPLE reported that the couple parted ways in early August, during a period when Davidson was on location filming in Australia and Kardashian was engaged with her business and family commitments in L.A.

An insider cited their demanding schedules as a contributing factor to the breakup, saying, “They are both constantly on the move and it was challenging.”

New Beginnings: Emily Ratajkowski

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Following his split from Kardashian, Davidson has been linked to actor and model Emily Ratajkowski. In November 2022, a source revealed to People that the budding romance, which has been flourishing for weeks, remains strong as “Emily continues to spend time with Pete.” They shared that she is charmed by his humor and finds him to be a thoughtful and enthusiastic date planner. Emily is proceeding with caution, feeling both intrigued and flattered by the attention. Speculation about their relationship started earlier in the month and appeared to be confirmed when Davidson and Ratajkowski were seen together at the celebration of the ‘Bodies Bodies Bodies’ actor’s 29th birthday, where they were spotted exchanging gifts. An insider from Us Weekly reported, “Pete and Emily have been in communication for a couple of months now,” and although it’s still very early, there is a mutual affection. They highlighted, “Pete has the ability to make Emily laugh, and he’s captivated by her intelligence.”

In December 2022, a source close to Emily told People that they had parted ways. “Em is single and totally happy,” the source said. “She will always prioritize her son, but enjoys dating when she has time. She enjoys her independence. She doesn’t have plans to see Pete again. She had fun with him, but she realized she didn’t want it to become anything else. She likes her life as it is.”

On the sets: Chase Sui Wonders

Pete Davidson's Relationships History: From Comedians to Pop Stars and Models

Davidson’s romantic ventures took a turn towards his professional sphere with actress Chase Sui Wonders. The duo, who co-starred in the film “Bodies, Bodies, Bodies,” were first spotted together in late 2022. Their relationship seemed to confirm when they were seen displaying affection at Universal Studios Hollywood in January 2023. Despite the PDA and time spent together, their relationship was relatively short-lived, with reports of their split emerging in August 2023. This breakup came around the same time Davidson had reportedly checked into rehab, continuing to openly manage his mental health challenges.

The Latest Chapter: Madelyn Cline

Madelyn Cline

As of late 2023, Davidson has been spotted with “Outer Banks” star Madelyn Cline, 25, fueling rumors of a new romantic connection. An insider informed US weekly, “Pete and Madelyn are in a relationship. They stayed overnight together at the Beverly Hills Hotel and followed it up with breakfast at the same place the next day. They maintained a very discreet presence and opted for a casual look, both donning baseball caps.”

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