A timeline of Pete Davidson's romantic escapades, from Ariana Grande to Kate Beckinsale

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Pete Davidson might be one of New York City’s biggest serial daters.

The “Saturday Night Live” star, 27, made headlines in 2018 for his brief, but highly public engagement to pop singing sensation, Ariana Grande, 28, within just a few weeks of dating.

But the couple split after a short five months, leading Grande to create her smashing breakup album, “thank u, next,” and Davidson to move on rather quickly with another celebrity, 48-year-old English actress Kate Beckinsale.

However, after splitting from Beckinsale in April 2019, the actor and stand-up comedian would go on to navigate other high-profile romances – many of them short-lived.

Read on for a look at some of Davidson’s most memorable relationship moments.

Aug. 21, 2021

Davidson and actress Phoebe Dynevor reportedly split after five months together as Davidson had started filming an upcoming rom-com with actress Kaley Cuoco, titled “Meet Cute,” while Dynevor starts production on season 2 of her Netflix series.

July 3, 2021

Davidson and Dynevor officially set their relationship status to public in July 2021.

The “Saturday Night Live” performer and “Bridgerton” star, 26, make their first appearance together in a social setting when they hit the courts as spectators during the Wimbledon Tennis Championships, and pictures snapped of the couple prove they’re smitten.

April 2021

Davidson hints that he’s dating the actress.

March 2021

Davidson and actress Phoebe Dynevor spark dating rumors when eyewitnesses see the couple getting close while they spent time in the United Kingdom.

Phoebe Dynevor resting her head on Pete Davidson’s shoulder at Wimbledon in July 2021.
(Karwai Tang/WireImage, File)

Jan. 15, 2020

Following earlier reports in January that Davidson and Kaia Gerber’s spark has fizzled, Davidson confirmed their breakup, explaining in February, “She’s very young, and I’m f–king going through a lot and it was before I went to rehab.”

He added, “It just wasn’t the right place or the right time at all.”

Nov. 31, 2019

After weeks of relationship rumors, Fox News confirms that Pete Davidson and Kaia Gerber, then 18, are officially together.

An insider claimed at the time that Gerber’s mom, supermodel Cindy Crawford, wanted Gerber to “keep it low-key at this point in the relationship, especially with all the Ariana Grande [Davidson’s ex-fiancee] stuff that has happened.” 

The source also pointed to Davidson and Gerber’s “age difference” at the time.

“Kaia is having fun and this is all new to her, so of course she would want to see what a relationship with someone like Pete would be like,” the source added at the time. “So far, she’s having a blast.”

A source confirmed to Fox News that Pete Davidson, 26, and Kaia Gerber, 16, were ‘definitely an item.’
(AP/Getty, File)

Oct. 18

A short-lived romance goes up in smoke just weeks after Margaret Qualley’s mother, actress Andie MacDowell, said they had a “nice” relationship.

“She has a beautiful relationship with him but I don’t want to step on her relationship too much,” she said in Sept. 2019, adding, “They have a nice relationship.”

August 31

Actress Margaret Qualley, then 24, and Davidson began dating in August 2019, Page Six confirmed at the time. The former couple was first spotted together in September 2019 after touching down at the Marco Polo airport in Venice. 

Comedian Pete Davidson and Margaret Qualley attending the ‘Seberg’ screening during the 76th Venice Film Festival at Sala Grande on Aug. 30, 2019 in Venice, Italy.
(Getty, File)

April 25

Davidson and Beckinsale reportedly call it quits in April 2019. Less than a week later, the comedian spends $400 at McDonald’s to feed his friends, the sold-out audience and the movie theater staff at a screening of “Avengers: Endgame.”

March 4

Davidson and Beckinsale confirm their relationship after they’re snapped kissing and cuddling at a New York Rangers game in NYC.

Kate Beckinsale and Pete Davidson attend a New York Rangers game on March 3, 2019.
(JD Images/REX/Shutterstock.)

Feb. 4

The new couple is spotted leaving his stand-up show in Los Angeles together and they’re holding hands.

8 Jan. 2019

Dating rumors begin after Davidson and 45-year-old Beckinsale leave a Golden Globes party together after supposedly flirting and talking all night long.

Nov. 5

Grande releases her new breakup song, “thank u, next.” in which she refers to all of her high publicized past relationships.

Oct. 22

During a stand-up routine in Los Angeles, Davidson pokes fun at his brief engagement with Grande.

Oct. 17

After filming a special performance for NBC’s “A Very Wicked Halloween,” Grande told her fans she needed some time away from social media. “Ok today was v special and I’m so grateful I was able to be there,” she wrote. “Time to say bye bye to the internet for just a lil bit. It’s hard not to bump news n stuff that I’m not tryna to see rn. It’s very sad and we’re all tryin very hard to keep goin. Love u. And thank u for bein here always.”

Oct. 15

After five months together, the couple called off their engagement and is officially broken up.

Sept. 17

The young couple gets a baby pig as a pet.

Aug. 20

Davidson and Grande step out in New York City for their red carpet debut at MTV Video Music Awards at Radio City Music Hall. She has included a song called “Pete” on her new album “Sweetener.”

June 21

Davidson talks to Jimmy Fallon on his late-night show about the engagement. “It’s f–king lit,” he said, “I feel like I won a contest.”

June 2018


Davidson and David begin to date. She’s the daughter of famed comedian/actor Larry David.

In September 2017, he told Entertainment Tonight, “I’m very lucky. She’s very, very supportive.”

They were together for two years, ending their relationship in May 2018. She also commented on Davidson’s sudden engagement to Grande, posting a photo on social media saying, “Been in Africa… What’d I miss??”


Davidson started dating comedian Carly Aquilino and they lasted for less than a year. She was part of the MTV series, “Girl Code,” and is also a stand-up comic.

Aquilino seemingly poked fun at Davidson’s rushed proposal when she posted a screenshot of a cryptic text message which she was sent in June 2018. It read, “I know I’m the 9 billionth person to text you today about this, but… I can’t.”

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