Pete Davidson might be one of New York City’s biggest serial daters.
But the couple split after a short five months, leading Grande to create her Grammy-nominated 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.
Nov. 3, 2021
Davidson and Kim Kardashian were spotted on two dates during the first week of November. On Nov. 3, the two were seen arriving separately at a private members’ social club called Zero Bond. They reportedly had dinner together.
The Skims founder, 41, and the comedian, 27, were also spotted on Nov. 2 dining together on Davidson’s native Staten Island.
Over Halloween weekend, Kardashian and Davidson were seen together on a ride at Knott’s Scary Farm in Southern California. They held hands while riding a roller coaster together. A source told People magazine, they do “have chemistry.”
The reality TV star hosted “SNL” on Oct. 9. They starred in a sketch together and kissed while playing Jasmine and Aladdin.
Aug. 21, 2021
Davidson and actress Phoebe Dynevor reportedly split after five months together just as Davidson started filming an upcoming rom-com with actress Kaley Cuoco, titled “Meet Cute.” Dynevor started production on Season 2 of her Netflix series.
July 3, 2021
Davidson and Dynevor officially make their relationship status known to the 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.
Davidson hints that he’s dating the actress.
Davidson and actress Phoebe Dynevor spark dating rumors when eyewitnesses see the couple getting close while they spent time in the United Kingdom.
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
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 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.”
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.
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.”
Davidson and Beckinsale confirm their relationship after they’re snapped kissing and cuddling at a New York Rangers game in NYC.
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.
Grande releases her new breakup song, “thank u, next.” in which she refers to all of her high publicized past relationships.
During a stand-up routine in Los Angeles, Davidson pokes fun at his brief engagement with Grande.
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.”
After five months together, the couple called off their engagement and is officially broken up.
The young couple gets a baby pig as a pet.
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.”
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.”
The couple is reportedly engaged and Davidson confirms the news with a photo of her massive ring on Instagram.
Memorial Day Weekend 2018
The new couple posts a photo of themselves roasting marshmallows on Instagram stories, but all we see are their hands. Then, a few days later they make their official debut on social media in full Harry Potter costumes — cloaks and all.
Davidson and Grande hang out at the “Saturday Night Live” after-party and news breaks later in the month that the two are definitely an item. They first met back in 2016 when the pop singer hosted “SNL,” but at that time she was dating rapper Mac Miller and he was with Cazzie David.
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.”