Ariana Grande and Mac Miller first went public with their relationship in September 2016

By Natalie Stone
September 07, 2018 08:45 PM
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Before Ariana Grande and her late ex-boyfriend Mac Miller began dating, the pair formed a deep friendship that began with one of their mutual loves: music.

Although the former couple called it quits earlier this year after almost two years of dating, the pair remained on good terms up until Miller’s death on Friday.

Miller (real name: Malcolm McCormick) was pronounced dead at 11:51 a.m. at his Studio City, California, home, the Los Angeles County Department of Medical Examiner-Coroner confirmed in a statement to PEOPLE. A cause of death is yet to be determined, but a source tells PEOPLE the rapper had gone into cardiac arrest after appearing to suffer a drug overdose.

Here’s a look back at Grande and Miller’s past relationship.

Started with Friendship

In September 2016, Grande confirmed her relationship with Miller on social media — but before that, the pair was good friends.

The rapper reached out to Grande when he thought she would be a great artist to feature on the track “My Favorite Part” on his fourth 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 in September 2016. “We made that song and started becoming close again. It’s very dope and I like how that worked out.”

Miller and Grande had previously collaborated on her hit song “The Way”, so it wasn’t the first time they’d worked together, but in this session it was like no time had passed.

“It was great. There was no awkwardness or weirdness, it was how it always was,” the rapper continued. “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.”

The two performed “My Favorite Part” at the weekly music series and their chemistry was fierce. At the end of the song, Grande shook Miller’s hand, as though to thank him jokingly for doing business with her, and walked off stage.

“Pleasure working with you,” he said, to which she replied: “I’ll be in touch.”

Kelsey McNeal/ABC via Getty

After the cameras stopped rolling, Grande went back on stage to put her hands on his shoulders and they shared a sweet moment. She cupped his face in her hands, leaned in and kissed him, at which point Miller kissed her right back.

“We hung out for a long time and everything just happened organically. We love making music together – we do that always,” said Miller. “But she’s my best friend in the world.”

Jeff Kravitz/FilmMagic

Two Years of Love

Miller had been Grande’s rock throughout their relationship, supporting her as she recovered emotionally after a suicide bombing occurred at her show on May 22 last year in Manchester, England. The terrorist attack killed 22 of the singer’s fans and injured 119 others.

On June 4, 2017, the “Side to Side” singer hosted the One Love Manchester concert attended by Miller. The two performed “The Way” and “Dang!” while also sharing a kiss on stage.

Earlier this year, the two were photographed together in March at Madonna’s private Oscars afterparty and remained by each other’s sides while holding hands in photos.

In April, the rapper raved about Grande on Twitter after she released her new single “No Tears Left to Cry.”

“No Tears Left to Cry” marked the first new music Grande had released since the Manchester bombing in May 2017.

“Very proud of this girl right here. Welcome back. We missed You. One of a kind,” Miller tweeted.

Kevin Mazur/One Love Manchester/Getty Images

Going Their Separate Ways

In May, PEOPLE confirmed that the pair had split.

The rapper and the singer decided to go their separate ways as their busy schedules became too much for the pair to continue as a couple, according to TMZ.

Following the split, Grande opened up about the breakup and called Miller one of her “favorite people on the planet.”

“This is one of my best friends in the whole world and favorite people on the planet,” Grande wrote of Miller 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!”

Mac Miller and Ariana Grande
GC Images

His Forever Cinderella

Although they had gone their separate ways, one aspect about their relationship will forever be immortalized in song.

While defending herself against accusations that she was responsible for Miller’s May DUI arrest, Grande revealed on that his song “Cinderella” is actually about her.

The news had the heads of Arianators spinning, as “Cinderella” — off of Miller’s latest album, The Divine Feminine — is filled with explicit lyrics about the couple’s more intimate moments in the bedroom.

“You in my dreams, that’s why I sleep all the time / Just to hear you say I love you, just to touch you,” Miller rapped in one of the more PG-rated lines.

Mac Miller and Ariana Grande
David X Prutting/BFA/REX/Shutterstock

Moving On

Shortly after their breakup, Grande began dating Pete Davidson, to whom she became engaged to in June. She denied cheating on Miller with Davidson.

Opening up about his past relationship with Grande during an interview with Zane Lowe on Beats 1 on Apple Music, Miller explained that they had both moved on since their split.

“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,” he said.

Courtesy of Beats 1 on Apple Music

Miller also went on to add that while some fans have assumed he’s “been on the Internet” following up on his ex’s every move following the news of her whirlwind romance with fiancé Davidson, that wasn’t the case.

Explaining why he’d taken a step back from things, the rapper remarked that not only was he about to drop his new album, “it just all seemed kind of unimportant you know — the need to show people I was OK.”

“It’s all positive energy,” he added. “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.”

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