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Miller and Grande first appeared together on her YouTube channel back in 2012, when they teamed up to record a cover of “Baby, It’s Cold Outside.” They quickly followed that up with a more high-profile collaboration: Grande’s hit 2013 single, “The Way.” While promoting the single, Grande told Hot 97 that Miller was one of her “best friends in the world, like in the whole world.”
Thanks to the flirty music video the couple filmed for “The Way” — a video that ends with them sharing a steamy kiss — many thought that they might have been more than just “best friends.” However, Miller quickly set the record straight.
“That’s the homey,” he told MTV News in 2013. “She’s got a boyfriend and everything. Obviously, that [kiss] made everyone talk. I didn’t even know that was going to happen, and then we were shooting and the director was like, ‘This should happen,’ and I’m like, ‘All right.’”
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TAKING IT UP A NOTCH
In July 2016, Grande split from her boyfriend of more than a year, Ricky Alvarez, and not long after that, the singer hit up Disneyland with Miller and her good friend Victoria Monét. Then, Miller made a few appearances on Grande’s Snapchat, when she chronicled a quest for Pokémon Go that she and some friends embarked on, and that was enough to get fans speculating that there was a new man in Grande’s life.
When Grande added a couple of “so fine and perfectly petite” tattoos to her fingers in August 2016, Miller was there by her side — and he even got a few new pieces of ink of his own.
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MADE ON MTV
Two days before the 2016 MTV VMAs, Grande and Miller were spotted out and about in New York City. The couple stopped by the Museum of Ice Cream (which Grande, naturally, chronicled on Snapchat), before hitting up a club later that night.
Grande gave a pretty good hint on the couple’s status during a pre-VMAs interview with host Charlamagne Tha God. After promising the radio personality that she would “send [Miller] your regards,” he asked Grande where the rapper was, and Grande responded, “Being supportive. It’s okay to be alone even when you have a boo.” She then went into the show, where she cuddled and giggled with Miller all night.
Days later, an adorable Instagram captioned simply “baabyyy” made things official.
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The two collaborated again on his song “My Favorite Part,” off his 2016 album The Divine Feminine.
“I wrote that love song before I saw her. We’re very good friends first and foremost,” Miller told PEOPLE at the taping of the AT&T Audience Network Presents series on Monday. “We made that song and started becoming close again. It’s very dope and I like how that worked out.
“It was great,” he continued. “There was no awkwardness or weirdness, it was how it always was. Just both of us older, more mature and more sure of ourselves. When we first recorded together we were young and figuring it out, which we still are, but now seeing her growth and my growth — it’s great.. We hung out for a long time and everything just happened organically. We love making music together – we do that always. But she’s my best friend in the world.”
“She’s just very warm and comforting,” he said. “She’s very caring but, also, we have a lot of fun. We go on adventures. Adventures can be driving around in the car aimlessly. It’s great to be able to do nothing and be doing so much.”
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Kevin Mazur/One Love Manchester/Getty Images
THERE FOR HER
In May 2017, tragedy struck when a suicide bomber killed dozens of fans outside of Grande’s concert at Manchester Arena in the U.K. Miller was Grande’s rock in the aftermath, and during her June 4 One Love Manchester concert, he joined her on stage for “The Way” and “Dang!”
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After keeping things quiet for a while, Miller and Grande surfaced at Madonna’s private post-Oscars party in L.A. The two coordinated in chic black ensembles and posted for photos, though didn’t speak to the press.
In April 2018, Grande released “No Tears Left to Cry,” her first single following the Manchester bombing — and Miller was the first to congratulate her.
“Very proud of this girl right here. Welcome Back. We missed You. One of a kind,” he tweeted.
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On May 9, 2018, PEOPLE confirmed Grande and Miller had split amicably, “as their busy schedules became too much for the pair to continue as a couple,” TMZ reported. A source later told PEOPLE, “Ariana and Mac officially broke up right after Coachella weekend, but they ultimately struggled for a long time with their relationship, and it was basically over last year.”
One day after the split, Grande broke her silence on Instagram.
“This is one of my best friends in the whole world and favorite people on the planet,” Grande wrote of Miller (real name: Malcolm McCormick) in an Instagram story. “I respect and adore him endlessly and am grateful to have him in my life in any form, at all times regardless of how our relationship changes or what the universe holds for each of us!”
In the post, Grande shared a throwback photo of them cuddling on a couch and added a heart-shaped emoji.
“Unconditional love is not selfish. It is wanting the best for that person even if at the moment, it’s not you,” Grande added. “I can’t wait to know and support you forever and i’m so proud of you!”
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Kelsey McNeal/ABC via Getty
When a Twitter user suggested the Grande split (and her subsequent relationship with Pete Davidson) was the reason Miller arrested and charged with DUI and hit and run in late May, the songstress clapped back, opening up about Miller’s addiction battles in the process.
“how absurd that you minimize female self-respect and self-worth by saying someone should stay in a toxic relationship because he wrote an album about them, which btw isn’t the case (just Cinderella is ab me).”
Grande’s Twitter statement continued: “I am not a babysitter or a mother and no woman should feel that they need to be. I have cared for him and tried to support his sobriety & prayed for his balance for years (and always will of course) but shaming / blaming women for a man’s inability to keep his s— together is a very major problem.”
“Let’s please stop doing that. of course i didn’t share about how hard or scary it was while it was happening but it was. i will continue to pray from the bottom of my heart that he figures it all out and that any other woman in this position does as well,” her response concluded.
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A FOND FAREWELL
In his final public chat about Grande in July, Miller told Zane Lowe of Beats 1 on Apple Music: “I was in love with somebody. We were together for two years. We worked through good times, bad times, stress and everything else. And then it came to an end and we both moved on. And it’s that simple.”
Of her engagement to Davidson, he said, “It’s all positive energy. I am happy for her and [the fact that she’s] moving forward with her life, just as I’m sure she is with me.”
A few weeks later, Grande slammed reports she’d cheated on Miller with Davidson.
On Sept. 7, 2018, Miller was found dead of an apparent overdose. He was 26.