A timeline of Pete Davidson's romantic escapades, from Ariana Grande to Kim Kardashian

Pete Davidson might be one of New York City's most prolific serial daters.

News broke Friday that Davidson, 28, and Kim Kardashian, 41, decided to part ways after nine months together. The couple "still have a lot of love for each other" but found that their conflicting schedules and distance apart "made it really difficult to maintain a relationship," a source told E! News.

The "Saturday Night Live" star made headlines in 2018 for his brief, yet highly public engagement to pop singing sensation Ariana Grande after a few weeks of dating.

But the couple split after five months, leading Grande to create her Grammy-nominated breakup album, "thank u, next." And Davidson moved on rather quickly to another celebrity, 49-year-old actress Kate Beckinsale.

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After splitting from Beckinsale in April 2019, the actor and stand-up comedian navigated other high-profile romances — many of them short-lived.

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

Aug. 5, 2022

Davidson and Kardashian have decided to part ways. E! News reported that the couple "still have a lot of love for each other" but long distance "made it really difficult to maintain a relationship."

Early on in their relationship, Davidson made Kim's mark permanent on his body by getting her name branded on his chest. He also has another tattoo in the "Keeping up with the Kardashians" star's honor that says "My girl is a lawyer."

The source told the outlet Davidson and Kardashian's split does not mean she is reigniting her relationship with estranged husband Kanye West.

"The divorce is moving ahead with Kanye," another source told E! News. "They are happily co-parenting."  

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 social club called Zero Bond. They reportedly had dinner together. 

The Skims founder and the comedian were also spotted Nov. 2 dining together on Davidson's native Staten Island.

TMZ reported the pair went to an Italian restaurant called Campania. Meanwhile, Page Six reported that Davidson booked the rooftop for them.

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October 2021

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 "have chemistry."

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The reality TV star hosted "SNL" 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 two of her Netflix series.

July 3, 2021

Davidson and Dynevor officially make their relationship status known to the public in July 2021.

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The "Saturday Night Live" performer and "Bridgerton" star, 27, 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 show they're smitten.

April 2021

Davidson hints that he's dating the Dynevor.

March 2021

Davidson and actress Phoebe Dynevor spark dating rumors when eyewitnesses see the couple getting close while spending 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---ing 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 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."

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 September 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. 

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.

Feb. 4

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

January 2019

Dating rumors begin after Davidson and 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 highly publicized past relationships.

Oct. 22

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

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Oct. 15

After five months together, Davidson and Grande called off their engagement and are officially broken up.

Sept. 17

Davidson and Grande a baby pig as a pet.

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Aug. 20

Davidson and Grande step out in New York City for their red carpet debut at the 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---ing lit," he said, "I feel like I won a contest."

June 2018

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.

May 2018

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 in 2016 when the pop singer hosted "SNL," but, at that time, she was dating rapper Mac Miller, and Davidson was with Cazzie David.

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2016

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

In September 2017, Davidson told "Entertainment Tonight," "I’m very lucky. She’s very, very supportive."

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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??"

2015

Davidson started dating comedian Carly Aquilino, and they lasted 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 she was sent in June 2018. It said, "I know I’m the 9 billionth person to text you today about this, but… I can’t."