Pete Davidson’s Spicy Love Life: From Larry David’s Daughter to Ariana Grande and Kim Kardashian, Every High-profile Woman Comedian Has Dated

30-year-old Pete Davidson has made headlines yet again, but not for his comedy this time. The Staten Island native has been equally famous for his self-deprecating humor as well as his high-profile relationships. From pop stars to reality TV royalty, Davidson has dated them all.

Recent reports suggest that Davidson and his last girlfriend, Outer Banks star Madelyn Cline, broke up after dating for less than a year. The ex-couple tried to maintain a quiet relationship. However, this new breakup adds another chapter to Davidson’s already colorful love life.

Pete Davidson’s Relationship History

• Carly Aquilino

From his engagement to Ariana Grande to his short stint with Kim Kardashian, Davidson’s love life has been anything but boring. The comedian first dated comedian-actress Carly Aquilino back in 2015. However, their relationship did not last long.

According to Us Weekly, she even took a shot at his engagement with Grande in 2018 by sharing a screenshot of a text message that read, “I know I’m the 9 billionth person to text you today about this, but… I can’t.” She captioned it by writing, “My day in a text message.” But later, the former couple did a movie together, The King of Staten Island.

• Cazzie David

His next popular girlfriend was Larry David‘s daughter, Cazzie David, whom he started dating in 2016. They had been in a relationship for approximately two years before they split in May 2018. In her book, No One Asked For This, David revealed that her breakup with the comic was tough for her.

She confessed that she “shook uncontrollably” in her father’s arms when she found out about his relationship with Ariana Grande through Davidson’s text. However, the former couple are now on good terms.

• Ariana Grande

After David, Pete Davidson had the next popular affair with pop icon Ariana Grande. Though they went for engagement after a few weeks of dating, their relationship was a very short one that lasted for a few months only. Still, this relationship brought Davidson under the spotlight for sure.

Davidson and Grande had a post-breakup feud that included indirect tweet responses, break-up songs, comments, and more. After Davidson made jokes about his relationship with Grande on SNL, she made a tweet where she indirectly poked Davidson for clinging to her name for relevancy (according to Insider). Her song thank u, next was also a response to the comedian. Davidson also talked about Grande in his Netflix special after she called their relationship a “distraction.”

• Kate Beckinsale

After Grande, Davidson has had several brief relationships with older women. In early 2019, he went out for a month with Kate Beckinsale, who is 20 years older than him. They were first spotted together at the Golden Globes afterparty.

They started dating in March 2019 and broke up a month later. According to Page Six, Beckinsale was not comfortable with the amount and way of media attention she was getting for her relationship with the comedian.

• Margaret Qualley

After that, Davidson was also linked to Margaret Qualley. The former couple was spotted together in August 2019 in Veince when Qualley was promoting her movie. Her mother even mentioned in an interview with People that they were having a nice relationship. However, the pair broke up in October 2019.

• Kaia Gerber

Davidson’s next relationship was with model Kaia Gerber for another short period of time. They were first spotted together in New York in November 2019. They dated until January 2020 and Davidson in an interview with Charlamagne Tha God revealed that the reason for their breakup was his mental condition.

Davidson revealed that he was having a tough time and went to rehab and he didn’t want Gerber to be stuck with someone who was having issues of his own.

• Olivia O’Brien

During the BFFs podcast, Olivia O’Brien revealed that she had a brief relationship with Davidson in October 2020. However, the comedian always denied their relationship. O’Brien on the other hand, mentioned that Davidson used to text her about him seeing somebody else, which caused the end of their brief relationship.

• Phoebe Dynevor

Phoebe Dynevor and Davidson’s rumors began when they were spotted together in Staffordshire for the first time in March 2021. The ex-couple was later seen in other public appearances and during the Wimbledon tournament.

However, they split up just 5 months after their first date, and their long-distance relationship was reportedly one of the major reasons behind that.

• Kim Kardashian

However, his love life took another turn when he began dating Kim Kardashian in December 2021. According to Hollywood Life, Davidson began dating when Kardashian was the host of SNL and their relationship only lasted for about nine months.

It was during this time that Davidson became a target of the media and paparazzi to a great extent. Their hectic work schedule was speculated to be one of the major reasons behind their split.

• Emily Ratajkowski

After Kardashian, Davidson dated model Emily Ratajkowski briefly. They started dating in November 2022 and their first meeting was made possible by a mutual friend (according to Us Weekly).

Ratajkowski was earlier seen praising the comedian’s personality on Late Night with Seth Meyers show. Although they had a good time together, the pair ended their relationship in December 2022.

• Chase Sui Wonders

Davidson then went on to have a serious relationship with his Bodies Bodies Bodies co-star Chase Sui Wonders. The pair was spotted together at his New York apartment just after his breakup with Ratajkowski.

TMZ also reported seeing them kissing and spending quality time together at Universal Studios Hollywood. According to Page Six, they dated for less than a year before splitting in August 2023.

• Madelyn Cline

And then comes his most recent relationship with Madelyn Cline, which has now also come to an end. According to Page Six, The pair started dating in September 2023. Cline was seen in one of Davidson’s standup shows in Las Vegas and was also by his side when he hosted the SNL premiere in October 2023.

As per The US Sun, Pete Davidson and Madelyn Cline have broken up after being together for 10 months. The couple officially came out in September 2023 for the first time after Davidson’s split from Chase Sui Wonders.

The last public appearance of Davidson and Cline together was in January 2024, when she went to watch one of the stand-up shows by Davidson in Philadelphia. After that, the couple stayed out of the media spotlight, which raised questions about the nature of their relationship.

Moreover, Davidson has been rather less active in the past year in particular. It is still unclear if this change in his lifestyle was one of the causes of his breakup or whether it was a result of their relationship troubles. 

Although the actual reasons for their breakup are unknown, Davidson’s series of short-lived relationships goes on. Some speculations say that he does not have time for serious relationships because of his work and possibly mental issues.

While talking to Variety, Davidson actually revealed his condition of borderline personality disorder and has been treated before for this condition. For now, it seems both he and Cline are moving forward separately, adding another chapter to the comedian’s ever-growing book of celebrity romances.