The Inside Scoop On Pete Davidson's Complete Dating History

Girl Code star Carly Aquilino is probably the least well-known of Davidson’s girlfriends, having dated him back in 2015 before he was the household name he is now. But there’s still a story there! Even though their relationship was reportedly only a casual one, Aquilino still had something to say on social media when Davidson’s love life began to make headlines.

Davidson and Ariana Grande got engaged on June 11, 2018, and mere hours after the news hit Aquilino posted a mysterious message. She shared a screenshot of a text message saying, “I know I’m the nine billionth person to text you today about this, but… I can’t,” and a caption reading, “My day in a text message.” Perhaps it would be fair to say she had mixed feelings.

Before the much-discussed engagement to Grande, Davidson was with a woman who very nearly shared his last name: Cazzie David. She’s actually the daughter of Larry David, the incredibly famous comedian, so no doubt the couple had something to talk about. Yet, despite the relationship by all accounts being a very serious one, it only lasted for two years.

According to David, she was dumped via text of all things. And then to add insult to injury Davidson got all the tattoos he had of her covered up. Ouch. Later she opened up about the split in her 2020 book No One Asked for This, and revealed she was heartbroken to discover Davidson had immediately fallen in love with Ariana Grande.

David wrote that she was haunted by the idea of Grande’s “baby voice whispering sweet nothings in his ear, dubbed over his past declarations of love and trust to me.” But believe it or not, despite everything she and Davidson were able to become friends in the end. She wrote to him in the acknowledgments section of her book, “I love you. Your bravery inspires me and your friendship means the world to me.”

After that came the big one, the headline-grabbing firestorm that was Davidson/Grande. It all started in May 2018, when an anonymous person told People magazine, “[Grande and Davidson] were backstage and he had his arm around her. They seemed very lovey-dovey. He was hanging out with her and her friends with his arm around her. She seemed quite smitten.” She was.

Grande and Davidson didn’t waste any time. Within a matter of weeks — yes, weeks — Davidson had gotten not one, but two, tattoos celebrating his union with her. Then came the bombshell. Only a month after meeting Grande, Davidson got engaged to her. Could they actually make it work long-term? Or would their fire burn out as quickly as it had sparked?

In June 2018 an insider told the website Hollywood Life, “Ariana is still on cloud nine from Pete’s proposal and incredible ring. He totally surprised her and stole her heart, she never thought she could be this in love. It’s a total whirlwind for Ariana and Pete, so they haven’t officially started planning [a wedding], but she’s got lots of ideas about what she wants.”

But plenty of people had reservations about the whole thing, including the guy who inked the Grande tattoos on Davidson. Artist Jon Mesa told Page Six in 2018, “After we were done, I told Pete, ‘Hey, dude, let’s just stop with the girlfriend tats until after [Grande’s] your wife. Because relationships come and go, and Pete is a really young man. [But] I think that went in one ear and out the other.”

And unfortunately, Mesa was right. The relationship started to crack fast. The attention from fans — not all of it positive — caused Davidson to delete his Instagram posts in July. Then, in a tragic turn of events, Grande’s ex-boyfriend Mac Miller died of an accidental drug overdose. She was devastated, and that was the beginning of the end for her and Davidson.

On 14 October, 2018, celeb gossip website TMZ broke the news. Davidson and Grande were over, the wedding was off, and the two were going their separate ways. An anonymous insider shortly after told People magazine, “It was way too much too soon. It’s not shocking to anyone.” And so Davidson once more had to get a tattoo covered up.

Less than a year after his split with Grande, Davidson hooked up with actress Kate Beckinsale. An insider told Page Six that after the Golden Globes awards that January, “They were being very flirty together, they were sitting very close on the outside patio seating. Kate had her hand on his knee, and she kept laughing at all his jokes.”

But the age gap between them raised a few eyebrows — Davidson was 25 and Beckinsale was 45. So, during one SNL skit, Davidson pointedly told the audience, “Apparently people have a crazy fascination with our age difference. It doesn’t really bother us, but then again, I’m new to this. So if you have any questions about a relationship with a big age difference, just ask…” and then rattled off a long list of male celebrities who’d dated younger women.

The Davidson-Beckinsale relationship ended just as quickly as it had begun. In April 2019 a source “familiar with the situation” told Entertainment Tonight, “They’re still friendly but are not on romantic terms,” and someone else told People that a long-distance relationship had been the death knell for them. Davidson was single again, but not for long.

A few months after breaking up with Beckinsale, Davidson started dating the daughter of actress Andie MacDowell, Margaret Qualley. They were first spotted together at the 2019 Venice Film Festival, but seemingly they weren’t ready to be “red carpet official” at that event. Instead, they apparently took the flight to Italy together but maintained a distance for the actual festival.

Andie MacDowell told People magazine in September 2019 that, although she hadn’t actually met Davidson, she was fully in support of her daughter dating him and called it “a beautiful relationship.” But just one month after that interview Davidson and Qualley split up, albeit without any public drama. And then, Davidson hooked up with another daughter of a ’90s icon.

In October 2019 Davidson started dating Kaia Gerber, the daughter of Rande Garber and famous supermodel Cindy Crawford. She takes after her mother in terms of looks, so you can definitely see where the attraction came from. Apparently Davidson tried to keep this relationship on the down-low, but it absolutely did not work. They were spotted getting very close during a holiday in Miami.

Apparently, Gerber’s parents weren’t too happy about her relationship with Davidson. An insider told The Post in December 2019, “I think they’re just hoping this could all fizzle out,” a source said. “[Kaia’s] traveling and working constantly — how serious can [she and Davidson] get? Kaia can be slightly naive. But she’s a smart girl with a good head on her shoulders and a family who watches out for her.”

Crawford got what she hoped for in the end. In February 2020 Davidson confirmed he and Gerber had split, and told Charlamagne Tha God in a YouTube interview, “It’s just like, she should be having fun. She shouldn’t have to worry about some dude that just has issues… It just wasn’t the right place or the right time at all.”

Did Olivia O’Brien actually date Pete Davidson or not? She claimed she had a fling with him after Kaia Gerber did, only for Davidson’s reps to come out and say that never happened. Later in 2022 she declared on Instagram, “I never claimed to date anyone. Stop trying to start weird drama over me texting someone two years ago.” Well, you be the judge.

In 2021 it emerged that Davidson was dating the star of hit period drama Bridgerton, Phoebe Dynevor. They lived in different countries, but apparently they were trying to make it work regardless. A source told Page Six in April, “Pete must like her if he’s flying off to quaint little English villages to hang out with her on set.”

Davidson himself more or less confirmed the relationship not long afterwards. Later that month, he did a question and answer session with students from Marquette University and was asked who his celebrity crush was. He answered, “I’m with my celebrity crush. That is all I can speak on.” The pair seemed very cute together, but could they go the distance?

Unfortunately, geography proved to be their undoing. By August they had split, and a source told The Sun, “Their mates think they make a great couple, but the distance has made it completely unworkable. They had fun and will remain close, but unless something drastic changes, their relationship won’t recover. It was wild while it lasted, and they both really care for each other.”

The relationship that broke the internet. In October 2021 Kim K appeared on Saturday Night Live and did an “Aladdin”-themed skit with Davidson. He was Aladdin, she was Jasmine, and they kissed on board a flying carpet. No-one thought anything of it at the time, it was just a bit of fun. But dramatic things were going on behind the scenes.

Kardashian told Harper’s Bazaar magazine in April 2022, “When we kissed, I was just like, ‘Really?’ But, yeah, it was a stage kiss, but it was, like, still like a little zing, you know? It wasn't anything like a super-crazy feeling. I was just like, ‘Hmm.’” And Davidson was interested, too. He asked around the SNL set for Kardashian’s number until he got it.

At the end of October 2021 the pair were spotted getting close at a Halloween event. But was it a serious relationship or a fling? Someone with inside information told E! News, “Kim isn’t looking to date anyone right now… There is no pressure between them.” But as the relationship got more and more serious, Davidson got… wait for it… another tattoo. An Aladdin one, to honor his and Kardashian’s first kiss.

But yep… that was yet another tattoo Davidson may have later regretted. In August 2022, not long after he got it, he and Kardashian went their separate ways. An anonymous source told E! News that the couple still had “a lot of love and respect for each other” but their busy lives “made it really difficult to maintain a relationship.”

There’s been no official word on whether the tattoo was removed, but Davidson was later seen with a bandage on his neck, so make of that what you will. Kardashian has no hard feelings, though. She told Interview magazine in September, “He’s literally such a good person, they don’t really make them like him anymore. I’m excited for what he has coming up.”

While Davidson was still dating Kim Kardashian he had a secret admirer from afar, and she was none other than world-renowned beauty Emily Ratajkowski. The model told Seth Meyers back in 2021, “Obviously women find [Davidson] very attractive. He seems super charming. He’s vulnerable. He’s lovely. His fingernail polish is awesome. He looks good!” So perhaps it shouldn’t come as a surprise that the year after that, she started dating him.

In November 2022, right after Ratajkowski divorced her husband of four years, news hit that she and Davidson were dating. An insider told Us magazine, “Pete and Emily have been talking for a couple months now… Pete makes Emily laugh and he loves how intelligent she is.” Everything sounds good so far, but do they just have too much baggage?

The internet is eagerly watching to see how this one pans out. One of the biggest emotions Twitter seems to be feeling, though, is bewilderment. “Someone needs to do a thesis study on how Pete Davidson managed to score Ariana Grande, Kim Kardashian, and Emily Ratajkowski in the same lifetime,” one person wrote. But he did it! Watch this space.