Phoebe Dynevor and Pete Davidson hosted by Lanson attend day 6 of the Wimbledon Tennis Championships at the All England Lawn Tennis and Croquet Club on July 03, 2021 in London, England. (Photo by Karwai Tang/WireImage)

Pete Davidson has been seen, in recent years, as sort of a household name in terms of romantics. The Saturday Night Live player has made his rounds among the women in Hollywood, but nothing has ever quite stuck for an extended period of time. Now, as unexpected rumors ramp up that Davidson and Kim Kardashian are involved with one another, whatever that may mean, we thought it would be interesting to take a look back at some of Pete Davidson’s past relationships to put his dating life in context. Y’know, for science.

Davidson doesn’t quite have a type, it seems. He seems to dip his toe into the dating pool with a variety of potential suitors, never quite sticking to one archetype. Regardless of this, it’s been interesting, to say the least, to watch Davidson’s romantic life over the years, and seeing it potentially develop into a fling with Kim Kardashian is unexpected, but the Kardashian sisters seem to have a thing for alternative men.

Let’s break these down.

Carly Aquilino, 2015

Carly Aquilino attends a taping of MTV’s new talk show “Girl Code Live”. “Girl Code Live” (Photo by Kevin Mazur/Getty Images for MTV)

Davidson had a brief fling with MTV Girl Code‘s Carly Aquilino in 2015. While not much is known about this particular relationship, we don’t quite know exactly how it ended either. When Aquilino found out about Davidson’s future engagement to Ariana Granda (stay tuned), she posted a picture to Instagram of a text message that read “I know I’m the 9 billionth person to text you today about this, but…I can’t,” with the caption “My day in a text message.”

So who knows what really went down with this one?

Cazzie David, 2016-2018

Pete Davidson and Cazzie David attend The Comedy Central Roast of Rob Lowe at Sony Studios on August 27, 2016 in Los Angeles, California. (Photo by Jeffrey Mayer/WireImage)

Aw, would you just look at the… uh, happy couple?

Let’s just say that for this one, things got a little weird. Davidson and David first started seeing each other casually in 2016, and then thing escalated into Davidson’s first long-term relationship in the public eye. Things seems to go good for a while, when all of a sudden in 2018, Davidson confirmed that the two had broken up in an interview with Complex’s “Open Late with Peter Rosenberg,”

“We’re not together anymore,” Davidson told Complex. “Very talented girl, she’ll be great and she’ll be fine. Yeah, I think she’ll be OK.”

I don’t know about you, but the way that is worded, it sounds to us like he was the one who ended things, and this turned out to be right. David released a collection of essays in 2020 titled “No One Asked For This,” where she broke down further details about the breakup. She revealed that both of them struggled with mental health issues during the relationship, and that Davidson broke up with her a day before it was announced that he was seeing Ariana Grande.


Ariana Grande, 2018

Ariana Grande and Pete Davidson are seen walking in Midtown on July 11, 2018 in New York City. (Photo by Raymond Hall/GC Images)

Well, here it is, the relationship that broke the internet.

When we found out that Davidson was dating Ariana Grande in 2018, nothing about it really made sense but we were just kind of going along for the ride, and enjoying it. Just a few weeks after it was announced that they were dating, it was then made official that the two were engaged, which is a little fast if I do say so myself.

They announced the engagement with a Harry Potter-themed photoshoot as well as a with a $93,000 pear-shaped ring, and it was later revealed that Davidson got two tattoos in Grande’s honor.

But not all that glitters is gold, and things came to an end very fast for this seemingly doe-eyed couple. After just five months together, the couple called off their engagement and their relationship. Davidson subsequently got both of the tattoos covered up.

Kate Beckinsale, 2019

Kate Beckinsale attends MIRROR Westfield Century City grand opening event  (Photo by Tommaso Boddi/Getty Images for The Mirror)

Who doesn’t love a 20-year age difference?

Romantic rumors started compiling after the two were seen flirting at a Golden Globes after party in January 2019. In very 2021 fashion, a lá Kourtney Kardashian and Travis Barker, the two were seen making out at a New York Rangers game in March 2019.

But, if we follow the pattern here, you’ll know things didn’t last for very long. Just after the public makeout session, the two split in April 2019. But what makes this seem different, and a little shocking, is that it seems like Beckinsale was the one to call it off.

“Even though Kate has been in Hollywood for a long time, she struggled with the attention on her relationship with Pete,” a source told Page Six. “He lives his life with his heart on his sleeve.”

Margaret Qualley, 2019

Pete Davidson and Margaret Qualley

Davidson had a busy 2019, romantically speaking.

This pairing reportedly started in August of 2019, and were later seen out and about together in Venice, Italy as Qualley was promoting her film Seberg, which screened at the Venice Film Festival that year.

But things ended pretty fast with this one, and in October 2019, the two called it quits. In September, right before the breakup, Qualley’s mother, Andie MacDowell, said of her daughter’s relationship “She has a beautiful relationship with him but I don’t want to step on her relationship too much,” MacDowell said, adding, “They have a nice relationship.”

Kaia Gerber, 2019-2020

Credit: MEGA

This was Davidson’s third romantic fling in 2019.

Right after things were called off with Margaret Qualley, like literally right after, it was revealed that Gerber and Davidson were dating in October 2019 during a romantic outing in Miami.

While the couple seemed happy, Page Six reported that Gerber’s parents, notably supermodel Cindy Crawford and Rande Gerber, hoped that the relationship would “fizzle out.”

Well, they got their wish. In January 2020, Gerber and Davidson called things off. This was right around the time that Davidson brought to light his struggles with mental health and checked himself into rehab.

“She’s very young, and I’m f–king going through a lot and it was before I went to rehab. It’s just like, she should be having fun,” Davidson told Charlamagne Tha God in a YouTube interview. “She shouldn’t have to worry about some dude that just has issues and s–t. She should be enjoying her work. It just wasn’t the right place or the right time at all.”

Phoebe Dynevor, 2021

Phoebe Dynevor and Pete Davidson  in London, England. (Photo by Karwai Tang/WireImage)

After his time in rehab and working on mental health, Davidson got back out into the dating game.

He and Bridgerton actress Phoebe Dynevor were reported to have started dating in March 2021 when Davidson flew from his native New York to England, where Dynevor lives to “spend time together.” While spend time they did, a source revealed that the relationship “wasn’t that serious.”

But with that being said, during a Zoom interview with Marquette University students, Davidson told them that he’s “with his celebrity crush,” and “That is all I can speak on.”

Unfortunately, Davidson and Dynevor didn’t last, breaking up five months after they started dating, calling things off in August 2021. At the end of the day, it was called off due to distance, but this one seemed kind of sweet, don’t you think?