How Ariana Grande's Relationship With Pete Davidson Really Began—and Why the Timing Was Perfect

The SNL star, who has a song named after him on Grande's Sweetener, still can't believe this is real life--and who wouldn't want to marry someone who feels that way about you?

By Natalie Finn Sep 26, 2018 10:00 AMTags
Pete Davidson, Ariana Grande, MTV Video Music Awards, VMAsNicholas Hunt/Getty Images for MTV

So far this year, no celebrity relationship story on its face seemed less destined to rent any long-term space in our consciousness than the news that Ariana Grande was dating Pete Davidson.

Both were just barely out of serious relationships, and Grande was coming upon the one-year anniversary of one of the most traumatizing events of her life. Then there was the whole "wait, but she's Ariana Grande and he's...that stoner kid from SNL" aspect of it.

Subsequently, when the public first got wind of their togetherness, the collective response was curiosity, chased with a healthy shot of skepticism.

"It's pretty dope, huh?" Davidson, already sporting two new Ariana-themed tattoos (he now has at least four), told a rapt audience at the Hollywood Improv in June.

"Everyone thinks they're really cute together," a source told E! News. "People don't realize what a great sense of humor she has. It makes them a good match. They're having a good time."

Then, with fate staring the jaded masses in the face over an 11, the universe decided to double down. Before anyone could even get used to Grande and Davidson as a couple, three weeks after we found out they were dating, they were engaged.

Ariana Grande & Pete Davidson: Romance Rewind

Not that Pete popping the question did a whole lot, initially, to quell the suspicion that theirs would still be a relatively short-lived romance. Engagements are entered into and broken every day, and not just between famous people.

But then June turned into July, then August, and now it's September...

"I'm a very, very lucky guy," Davidson said on The Howard Stern Show Monday. "Yeah, I don't know what's going on."

That's Pete being self-deprecating, as always. He used to only have one mode—that he's undeserving of good things, such as his gig on Saturday Night Live—and that's still his primary mode, but now he's also consumed with marveling over his luck in love, the unfamiliar feeling that is happiness.

Stern asked whether his habitual self-loathing and its potential to torpedo a relationship was a concern, but Davidson said, simply, "It was until I met her."


"I just think some people are meant to be together and some people aren't," he explained. "Even if they're good people or not, some people just aren't good in relationships together, and I just think we're supposed to be together." He also said, "I feel safe."

At the same time, he cracked, "Any time we're intimate I'm always apologizing and saying thank you. I swear to god, I'm like, 'you're awesome for doing this, thank you so much.' I'm so grateful that she touches me."

But concern that Davidson, who brings to the table a set of issues that he's been endearingly open about, may not be what Grande needs right now, or ever, is falling by the wayside. Not that the 24-year-old comedian, who became the youngest-ever SNL cast member when he was hired at 20, needed to be proving himself to anyone other than Grande. But he's been proving himself all the same.

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"I have no wish," Grande captioned a photo on her Instagram Story on June 25, the night before her 25th birthday. "I have everything I ever wanted hi." The photo was of her fiancé.

Minutes after midnight, Davidson posted, "Happy birthday to the most precious angel on earth! you're my favorite person that ever existed �� i love you sm."

"I'm not like a very traditional person, so the fact that I'm even getting married is something I never even saw coming," Grande said on The Zach Sang Show in August. "I never saw that coming, like, I never wanted that, like, I was, 'F--k that, there's no point.' I was like, 'What's the point?' And then I kinda understood it when it was like, with the right person."


The two of them first met when Grande hosted and performed on SNL in March 2016—and as it turns out, hindsight is X-ray vision. 

"We never exchanged numbers or anything, we weren't even like friends for a long time," Grande recalled last month on The Tonight Show Starring Jimmy Fallon, "but I had the biggest crush in the whole world on him the whole time, like forever. My friends used to make fun of me."

She never said anything, figuring "like, whatever"—as in, what am I really supposed to do about it?

Grande remembered leaving the writers room meeting at SNL that week—"and I'm not a crushy person, I don't have crushes on people I don't know, I'm not crushy"—and jokingly telling her tour manager, "'I'm marrying him, 100 percent.' I was like, 'I'm literally marrying him.'"

Davidson, as much as he can't believe anything about the state of his life right now, really can't get over that one.


On The Howard Stern Show, Davidson remembered feeling like he totally blew it that day.

"When she left [the room], I was like, 'what a f--king idiot I am." In a mocking tone, he added, "Oh, good joke you pitched!" He doesn't remember what he pitched, if anything, or how it was received. "I was just, like, staring at her," he said.

However, he did seize the moment when it finally came.

"The day I met her, I was like, 'Hey, I'll marry you tomorrow,'" he told GQ this summer. "She was calling my bluff. I sent her a picture [of rings]. I was like, 'Do you like any of these?' She was like, 'Those are my favorite ones,' and I was like, 'Sick.'"

What Grande ended up with is a custom 3-carat pear-shaped diamond ring from New York jeweler Greg Yuna, who got a call from the besotted Davidson in late May, a couple weeks into their relationship.

Kevin Mazur/Getty Images for Songwriters Hall Of Fame

"He didn't tell me who it was for but told me to keep it a secret. He didn't tell me anything about it," Yuna told E! News. The Staten Island native paid $93,000 for the ring, which was first spotted on Grande's finger on June 2 when she performed at Wango Tango in L.A.

"We were in bed hanging, after watching a movie. I was like, 'Will you marry me?' It was really dope," Davidson told Variety last month. 

"He didn't get on the knee or anything, thank God," Grande said on The Zach Sang Show. "...Oh my God, that would've been so googly."

Talking about their engagement when he was on The Tonight Show, Davidson admitted, "It's f--king lit, Jimmy." He joked that men had started tipping their hats to him in the street, as if he were a hero. Grande was watching his appearance from the side of the stage.

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He didn't know how to go about asking her out in the first place, Davidson insisted to Stern, but "timing, I feel like, is everything. We both were in a similar situation at the same time," both newly single, and fate in the form of Scooter Braun—Ariana's manager—intervened. "Booking my career and wife," Davidson quipped.

"It was a rough time," he recalled, due to "an assortment of s--t." For him, "everything feels so extreme, dude, like it's the most extreme or the least extreme."

Braun told him that Grande was interested. "I thought he was just full of -s--t," Davidson cracked. But he got in touch and went over to Grande's place, and he remembers that "she was coming from the Met thing." The Met Gala being something he, on his own, would avoid like the plague, but would go to if she asked.

A group of about 10 had fun for a couple of hours playing Quiplash, but then eventually it was just the two of them. "I'm so stupid and unaware of how chemistry and all that stuff works, I was literally, 'Hi, can I kiss you, please?'" 

Grande confirmed as much on Nicki Minaj's Queen Radio last month, revealing that he asked permission. It was "really sweet" and "really sexy," she said.


"Universe must have my back, fell from the sky into my lap / and I know you know that you're my soulmate and all that," the artist sings on "Pete Davidson," which she wrote a week after they started dating and can be found on her latest album, Sweetener.

"I just made it and I sent to him, and I didn't know what to call it. So I just called it 'Pete,'" Grande said on The Tonight Show. "It was either going to be that or, like, 'This Is About Pete Davidson.' I was like, why not? Be direct."

"I've never seen you more happy," Fallon told her.

Davidson told Stern that, because he was happy for a change, he was more excited to do everything, including work. And Grande told Paper magazine that he is "really supportive and just a positive thing all around in my life." The families have, of course, met and Pete's mom, Amy, is nuts about Ariana and, equally important, Ariana's beloved Nonna adores Pete.

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They have a wedding "game plan," Davidson says, and in the meantime the betrothed couple are cohabitating with their new potbellied pig, Piggy Smalls, in a 4,000-square-foot unit in a posh building in Manhattan's Chelsea neighborhood—which, Davidson isn't shy to say, belongs to Grande (price tag: a reported $16 million) and he's grateful to be living in it with her.

"It's like, we have six beanbags, but we have no forks—you know what I mean?" he told GQ this summer. "We're learning how to be adults. We're having a really fun time."

But while Grande's been famous since she was a kid, making her Broadway debut at 15 and then starring on Nickelodeon's Victorious and the spin-off Sam & Kat, Davidson is still getting used to this heightened level of scrutiny. He wasn't really used to being known at all, and now...people can't get enough.

"I gotta tell you, up until about two months ago, if someone wrote about me, I saw it," he told GQ. "Nobody gave a s--t two months ago, so anytime there was an article, I would obviously see it, because my mom would send it to me and be like, 'Yaaay!'" Now, he told the magazine, he enjoys driving around alone at night, just to get some peace and quiet.

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Davidson scrubbed his Instagram account in July, and though he briefly returned—he posted a video last week of himself heckling some paparazzi angling for a photo—now he tells Stern he's over it and doesn't have his password. That one video has since been deleted, surely to the disappointment of his 2.5 million followers. He's not on Twitter, either.

"No, there's nothing wrong," he explained via Instagram Story in July. "No, nothing happened. No, there's nothing cryptic about anything. I just don't wanna be on Instagram anymore. Or any social media platform. The internet is an evil place and it doesn't make me feel good. Why should I spend any time on negative energy when my real life is f--king lit. The fact that I even have to say this proves my point. I love you all and I'm sure I'll be back at some point."

Instagram Stories

He purged his Instagram, however, the day after leaving what he surely thought was an innocent comment on a photo that Grande posted in tribute to her late grandfather on the fourth anniversary of his death. "omg what a cutie," he wrote, much to the dismay of the comment police.

"Are you guys all insane?" Davidson replied a few hours later. "i was talking about how cute her grandpa is. what's wrong with that? you guys will really look for anything to attack people. it's sad."

Grande perseveres on social media, meanwhile, as her 129 million Instagram followers count on her to do. Davidson had his share of "get me off this thing!!" moments—"I got a death threat; someone wanted to shoot me in the face because she's so hot. You know how insane that is?" he told Stern—Grande has had plenty of her own reasons to take a break as well.

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After she and Mac Miller broke up in early May, and then he was arrested following a DUI crash, she was hounded to the point that she eventually was compelled to respond, explaining that she cared for Miller, but that they had a "toxic relationship" and she wasn't going to be his babysitter forever. Critics bugged her for naming a song "Pete Davidson" after they'd only been together for a short period of time. Then, when Miller died of an apparent overdose on Sept. 7, the singer would've been wise to ignore all comments or "@'s" altogether.

Grande, suffice it to say, was devastated.

She and Davidson were originally planning on going to the Emmys together last week, but decided to skip it. "Given the events of the past couple of years, Ariana is going to take some much needed time to heal and mend," her rep said in a statement. "She will be staying close to home and using this period to spend time with her loved ones and work on new music without deadline. She thanks her fans for their understanding."

Evan Agostini/Invision/AP/REX/Shutterstock

Indeed, this has been an unfathomably trying period for Grande, who had just finished performing at Manchester Arena on May 22, 2017, when a terrorist's bomb exploded outside, killing 22 people, as well as the bomber. Miller was there to support her through that, and he joined her onstage when she headlined a benefit concert for survivors and victims' families that July. The rapper, however, had struggled with substance abuse for years, and ultimately she could only do so much for so long if he didn't want her help. 

So, when you think about it, she may be a woman of fewer spoken grateful words than her fiancé, but she's probably in just as much disbelief that, amid all that's gone wrong, she found happiness—and with a guy who loves her so damn much and will do anything for her.

Even go to the Met Gala.

Davidson may still feel inclined to pinch himself, but he told Stern, "I'm just f--king lucky and I hope I don't wake up."