Naturally, the news of Ariana and Mac's split didn't sit well with fans, as heartbreak and crying emojis have since flooded the artists' Instagram comment section. Mac, who had a run-in with the law earlier this month and was charged with drunk driving and hit-and-run, has remained mum on all of his socials, while Ariana has been prepping her upcoming album following the release of her new song "No Tears Left To Cry."
Below, Billboard takes a look back at Ariana Grande and Mac Miller's relationship history.
The Twitter conversation that started it all (November 2012)
In November 2012, Ariana Grande was watching the annual Macy’s Thanksgiving Day Parade and asked her followers, “What are you thankful for at the moment?” Mac Miller responded and said, “the velvet revival,” which was the start of their first-ever conversation that ended with Mac, or rather his alter ego Larry Lovestein, requesting to do a duet with the then-Nickelodeon star. The pair teamed up to do a cover of the Christmas classic of “Baby It’s Cold Outside” just in time for the holiday season.
Mac and Ariana lock lips in “The Way" (March 2013)
Following their Christmas duet, Ariana heard the Big Pun-sampling “The Way” from producer Harry Samuels and felt like Mac would be the perfect addition to the track. “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. What do you think?' And he said, 'Sounds like a hit to me!' she told Billboard in 2013.
In the light-hearted visual for “The Way,” Ariana and Mac flirt throughout the video, from Ariana landing a kiss on Mac’s cheek to Mac taking photos of the singer. Towards the end of the video, the chemistry between the two had already heat up and led to more kissing, fueling relationship rumors.
“That's the homie. She's got a boyfriend and everything,” he told MTV News in April of 2013. “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, 'Alright.'”
Mac calls Ariana “the greatest person in the world" (July 2013)
Mac couldn’t dodge Ariana questions after “The Way” kiss, but even though they weren’t dating -- she was reportedly dating YouTube star Jai Brooks at the time -- Mac had nothing but sweet things to say about Ariana.
“She’s like the greatest person in the world,” he said. “She’s like an angel, she’s very nice, she’s a sweet girl.”
Ariana gave "The Way" kiss with Mac Miller a 1/10 score (July 2013)
While visiting Los Angeles' Power 106 radio station, J Cruz asked the singer to rate her kiss with Mac. "I'm gonna say a one just 'cause the cigarettes," she said but insisted she wasn't insulting Mac and said, "he's a great, great, great guy."
Mac hops on the remix of Ariana’s single “Into You” (August 2016)
In August 2016, Mac and Ariana reunited for the remix of the singer’s track “Into You.” Before reuniting with Mac, Ariana was in a relationship with Big Sean, who collaborated with the singer on “Right There” from her album Yours Truly. After releasing the “Into You” remix, Mac and Ariana were spotted kissing at a restaurant in Encino, CA.
Mac and Ariana go public with their relationship (August 2016)
The couple took their romance public at the 2016 MTV VMA Awards and was seen cuddling with each other at a VMA Awards after party hosted by Republic Records.
Ariana makes her relationship Instagram official (September 2016)
In today’s social media-driven world, a relationship isn’t really official until it’s Instagram official, and Ariana made it clear who had her heart. The singer posted a photo of her laughing while holding Mac in a headlock with the caption, “baabyyy.” Ariana also stopped by The Ellen DeGeneres show and confirmed her relationship with Mac.
"This is so crazy. I’ve never had the relationship talk on a show before," she told the host. She blushed when Ellen asked if she was happy with Mac and the singer replied, "Yeah."
Mac releases “My Favorite Part” featuring Ariana (September 2016)
The newly minted couple joined forces again for the slow-burning, jazzy “My Favorite Part” from Mac Miller’s 2016 album The Divine Feminine. On “My Favorite Part,” Mac raps about how beautiful his lady is before the pair’s voices blend together for the hook.
Speaking to People about his duet with Ariana, Mac said, “I wrote that love song before I saw her. We’re very good friends first and foremost,” Miller said. “We made that song and started becoming close again. It’s very dope and I like how that worked out.”
He added, “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.”
Mac Miller comforts Ariana following Manchester terrorist attack (May 2017)
Tragedy struck an Ariana Grande concert in Manchester in May 2017, as 22 concert attendees were killed following the attack. When Ariana touched down in the states to return home, her boyfriend Mac was there at the airport to welcome her home. In a photo captured by paparazzi, Mac and Ariana kissed when she exited the plane.
Mac canceled a few of his festival performances to be by Ariana's side following the attack. When Ariana returned to Manchester a month later for her benefit concert, Mac supported the singer by joining her on stage to perform "The Way."
Mac Miller sends a sweet birthday message to Ariana (June 2017)
Mac shared a black and white photo of him and Ariana making silly faces in honor of the singer's birthday. "Happy Birthday to this adorable pure soul who has reminded me what being happy feels like," he captioned the photo. "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."
Mac praises his girlfriend for her comeback single "No Tears Left to Cry" (April 2018)
Ariana returned to music with the jovial, bouncy track "No Tears Left to Cry" in April 2018. Mac, being the supportive boyfriend he is, shared her single on his Twitter page and wrote, "very proud of this girl right here [??] Welcome back. We missed you. One of a kind." On the heels of her new single, Ariana took the stage at Coachella with Mac right there by her side. The couple was spotted cuddling and kissing at the festival.
Ariana announces that she and Mac have parted ways (May 2018)
Earlier in May, TMZ reported that Ariana and Mac broke up but remain friends. A few days after reports began to circulate, Ariana confirmed the breakup in a post on her Instagram Stories. "This is one of my best friends in the whole world and favorite people on the planet,” Grande wrote. “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!”
At the end of the message, Ariana wrote that "unconditional love is not selfish. It is wanting the best for someone even if at the moment, it's not you." She added that she'll still support him and is proud of him.
Ariana shuts down a fan who blames her for the breakup (May 2018)
After Ariana confirmed that she and Mac broke up, Mac was arrested for drunk driving and hit-and-run after crashing his Mercedes G-Wagon. Following his crash, several outlets reported that Ariana had moved on to "casually date" Saturday Night Live comedian Pete Davidson. Many fans didn't take the news well, especially one fan who tried to blame Ariana for Mac latest antics.
"Mac Miller totalling his G wagon and getting a DUI after Ariana Grande dumped him for another dude after he poured his heart out on a ten song album to her called the divine feminine is just the most heartbreaking thing happening in Hollywood," the Twitter user wrote. Ariana caught wind of his comments and shared a long message explaining what caused the demise of her relationship.
"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)," she wrote. "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 and prayed for his balance for years (and always will of course) but shaming/blaming women for a man’s inability to keep his shit together is a very major problem. Let’s please stop doing that.”
She added that she'll continue to pray for Mac and other women who may be in similar situations.