Pete Davidson’s Complete Dating History Has Left Us With Many Questions

Mainly... can he drop his flirting tips?
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Pete Davidson has become the Adonis of Hollywood.

There is something so clearly captivating about the comedian… just ask Ariana Grande, Kaia Gerber, Kate Beckinsale, and all the other gorgeous women who have dated him.

WATCH: The moment Pete Davidson knew his engagement was over

And now his magnetism has allured Kim freakin Kardashian.

Seriously drop your dating advice King!! Or like, could you host a ‘How to flirt with gorgeous women 101’ Zoom or something?? DM us x

Everyone is in agreement that this man has moves. Paige on Twitter (@BonerWizard) even noted that “if princess Diana were alive today she would be dating Pete Davidson”. She’s not wrong. 

We will say, that while everyone virtually high-fives Pete and calls him a legend for his extensive dating resume… pour one out for Taylor Swift and any other female who has been slut shamed for the same reason.

It’s the double standards for us… but we digress.

We’ve broken down all of Pete’s relationships right here and, honestly, this is one Met Gala table we’d love to sit at.

Carly Aquilino. (Credit: Getty)

Carly Aquilino

In 2015, The Saturday Night Live performer briefly dated fellow comedian Carly Aquilino, who you may recognise from MTV’s Girl Code.

But things seemed to end amicably between the pair, with Carly even making an appearance in Pete’s 2020 film The King of Staten Island.

Cazzie David and Pete Davidson. (Credit: Getty)

Cazzie David

A year after his split from Carly, Pete entered a two-year relationship with comedian Larry David’s daughter, Cazzie.

The actor sadly confirmed they had broken up in May, 2018.

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

According to Hollywood Life, after their breakup, Cazzie regretted the decision, but Pete had already moved on to the one and only Ariana Grande.

Pete Davidson and Ariana Grande. (Credit: Getty)

Ariana Grande

In May 2018, Ariana Grande and Pete Davidson stepped out together as a couple and metaphorically grabbed the media in a chokehold.

Ari originally met Pete when she was a musical guest on SNL in 2016. She later confessed she was instantly attracted to him and even pictured herself marrying him.

Well, it’s like Ari says, “I see it, I like it, I want it, I got it” because two years later, in June of 2018, the couple were engaged.

Pete and Ari were so clearly infatuated with each other, having a very public romance.

The Break Free singer even penned a song called Pete Davidson for her Sweetener album. And the SNL star committed to his fiancée by getting an Ari inspired tattoo on his neck (that didn’t age well).

Sadly for all the Pete and Ari shippers, four months after announcing their engagement, the pair called things off.

But during SNL’s Weekend Update segment in November, Pete proved there was no bad blood between the pair.

“She’s a wonderful, strong person, and I genuinely wish her all the happiness in the world,” he said.

Oh, and he also covered up the tatt.

Kate Beckinsale. (Credit: Getty)

Kate Beckinsale

A year after dating the thank u next singer, around March 2019, Pete was spotted with actress Kate Beckinsale; the couple were even photographed making out at a New York Rangers game.

Ari gave the new lovers her stamp of approval, telling TMZ reporters they were “so cute” when queried about her ex-fiancé.

While dating Pete, Kate, who is 20 years his senior, spoke about the new relationship to The Los Angeles Times.

“I’ve never been in this position before — never dated anybody who comes with their own bag of mischief,” she said. “It’s all quite shocking, and something to get used to. I think if you liked the person less, you would bow out of it. If that were the main thrust of the relationship, there would be a problem. But it’s not.”

Sadly, they split a month later.

Margaret Qualley. (Credit: Getty)

Margaret Qualley

During Pete’s ✨hot girl Italian summer ✨ he started dating Once Up A Time… In Hollywood actress, Margaret Qualley.

At the time, Margaret’s mother, actress Andie MacDowell, spoke about her daughter’s “beautiful” relationship with the comedian.

“I don’t want to step on her relationship too much,” she said, according to Page Six. “They have a nice relationship.”

But despite Venice being one of the most romantic cities in the world, it wasn’t enough to keep the spark alive, and the pair broke up in October. 

Kaia Gerber. (Credit: Getty)

Kaia Gerber

A month later, Pete was spotted in Miami with model Kaia Gerber – the daughter of Cindy Crawford and Rande Gerber.

The pair reportedly broke things off in January 2020, not long before the actor checked into rehab. In a later interview with Charlamagne tha God, Pete revealed that things didn’t work out because he was “going through a lot”.

“It’s just like, she should be having fun,” he said. “She shouldn’t have to worry about some dude that just has issues and s–t. She should be enjoying her work.”

The comedian added: “It just wasn’t the right place or the right time at all.”

Pete also said that Kaia was “beautiful” and “smarter” than him.

“If anyone was worried that I was too smart or advanced for her, they do not have to worry at all. She was way, way smarter than I was.”

Phoebe Dynevor and Pete Davidson. (Credit: Getty)

Phoebe Dynevor

It was the Saturday Night Live + Bridgerton romance that no one knew they needed. 

Pete and Phoebe set Twitter into a frenzy after attending the U.K.’s Wimbledon together in July this year. Phoebe was spotted resting her head on the comedian’s shoulder while he kissed her forehead. Move over Duke of Hastings. 

Three months earlier, a source told E! News that Pete was “very into” the Bridgerton star and was even flying between New York City (where SNL is filmed) to the U.K. where the actress was reportedly filming season two of the Netflix show.

While Pete never confirmed his relationship with the English actress, he did speak candidly about his relationships on iHeartRadio’s The Breakfast Club back in May, around the time rumours were circulating.

“I am just very, very honest,” the 27-year-old said. “I think what a lot of people do is they try to put on—not even their best self—but almost a version of themself that they would like to be. And eventually, that will unravel, you know?

“So, I just, off the top, I’m like, ‘Hey, I’m nuts. Here’s all my issues. Here’s what I do. Here’s the therapists. This is what happens.’ And that can either be a lot for someone…or they could be like, ‘Cool, that was really refreshingly honest.’ Or, sometimes it can be a little intense and weird and people can’t handle that stuff.”

But four months after stepping out in public together, the pair called it quits.

“The long distance made it very difficult,” a source told E! News regarding the split. “They had fun, but it wasn’t sustainable being so far apart. It was great while it lasted, but they both agreed it was best to move on.”

Kim Kardashian. (Credit: Getty)

Kim Kardashian

Kanye West has left the chat.

Following Kim’s stint on SNL in October, she and Pete have been spotted hanging out…. a lot.

On Friday October 29th, Kim and Pete visited the Knott’s Berry Farm theme park in California (call us when you’ve been to Movie World guys. Sincerely, Australia x).

The pair were accompanied by a group of friends and family, including newly engaged couple Kourtney Kardashian and Travis Barker.

Things got interesting when Kim and Pete were pictured holding hands while on one of the rides.

THEN Kim visited Pete in his hometown of Staten Island where he took her to a pizzeria.

But sources close to the celebs say they’re just friends… for now.

“They hang in the same circles so they will be together from time to time,” a source told PEOPLE magazine. “It’s just friends hanging out.”

However! ☝️A different insider told Us Weekly that “no one really knows but’s going on” between the celebrities, but that “things could turn romantic”. Hmmm OK.

And another source told the same publication that the KUWTK star was “surprised” by the amount of chemistry she and Pete have. Yeah… that makes two of us, babes.

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