Ariana Grande and Mac Miller‘s relationship will always be one for the books.
The exes were friends for years before taking their relationship to the next level. The artists were first linked in 2012 after a flirty Twitter exchange led them to collaborate on a remake of the hit 1944 Christmas song, “Baby It’s Cold Outside.”
The following year, Grande and Miller (real name Malcolm McCormick) linked up again for the two-time Grammy Award winner’s single, “The Way,” in which they locked lips onscreen.
In 2016, the longtime friends took their romance public, going Instagram official in September that year.
Ariana Grande’s Dating History In Photos: A Timeline of Her Exes and Flings
The pair dated for nearly two years before amicably calling it quits in May 2018. In September that year, news broke that Miller had died of an accidental overdose, Us Weekly confirmed. He was 26 years old.
“I adored you from the day I met you when I was 19 and I always will,” Grande wrote in a tribute via Instagram after his death. “I can’t believe you aren’t here anymore. I really can’t wrap my head around it. We talked about this. So many times. I’m so mad, I’m so sad, I don’t know what to do. You were my dearest friend. For so long. Above anything else. I’m so sorry I couldn’t fix or take your pain away. I really wanted to. The kindest, sweetest soul with demons he never deserved. I hope you’re okay now. Rest.”
Keep reading for a look back at Ariana Grande and Mac Miller’s relationship.
2012
The duo sang together on the unreleased track, “Baby It’s Cold Outside.”
2013
After they collaborated on Grande’s single, “The Way,” the Victorious alum opened up about recording the song with Miller.
“I cut my vocal on it, and then Mac and I had been hanging out for a while at that point, and I was like, ‘I really want you to feature on this record,” she told Billboard at the time, adding that she asked, “‘What do you think?’ And he said, ‘Sounds like a hit to me!’”
August 2016
Grande and Miller were spotted getting cozy together at a VMAs afterparty hosted by Republic Records.
September 2016
Grande was featured on Miller’s single, “My Favorite Part,” the same month they made their relationship Instagram official.
The Don’t Look Up actress opened up about dating the rapper during an appearance on The Ellen DeGeneres Show.
“This is so crazy. I’ve never had the relationship talk on a show before,” Grande told host Ellen DeGeneres.
May 2017
After Grande’s concert at Britain’s Manchester Arena was bombed, Miller canceled a string of performances to be by her side.
June 2017
Miller made a surprise appearance at Grande’s Manchester benefit concert, where the duo performed “The Way.”
That same month, Miller posted a sweet tribute to the singer in honor of her birthday.
“Happy Birthday to this adorable pure soul who has reminded me what being happy feels like,” he wrote. “Thank you for loving me so good. I think it’s supposed to be ‘so well’ but I don’t care. I love you and can’t wait for all of the adventures.”
April 2018
Miller was by Grande’s side as she performed at Coachella that year. The pair were also seen cuddling and kissing during the festival.
May 2018
Grande and Miller amicably parted ways after nearly two years together, Us Weekly confirmed.
September 2018
Miller died on September 7, 2018. At the time, the Los Angeles Police Department told Us that authorities responded to the “Self Care” rapper’s home in the San Fernando Valley area just before noon. He was pronounced dead at the scene.
August 2019
Nearly a year after his death, Grande reflected on her and Miller’s relationship in an interview with Vogue.
“By no means was what we had perfect, but, like, f–k. He was the best person ever, and he didn’t deserve the demons he had,” she told the magazine. “I was the glue for such a long time, and I found myself becoming… less and less sticky. The pieces just started to float away.”
