Courtesy of Instagram

So heartbreaking! Ariana Grande had a beautiful friendship with Mac Miller before they began dating. Now that their romance has ended, we have a timeline of their love.

Who saw this one coming? Ariana Grande, 24, and rapper Mac Miller, 26, have heartbreakingly split after a year and a half long romance. The couple had been pals and collaborators for years before taking their relationship to the next level, officially coming out as a couple in Sept. of 2016. Mac had been by Ariana’s side as her love affair with Big Sean, 30, fizzled in 2015, and he eventually became the main man in the “Side to Side” singer’s life. TMZ reported on May 9 that the pair had decided to go their separate ways because of their busy schedules, but planned to remain close pals. We’ve got a timeline on their relationship.

It all started when Mac tweeted to Ariana in Nov. of 2012 that he’d like to hit the studio with her and she responded that she’d love to. Just a few weeks later they made it happen! They came out with the duet “Baby It’s Cold Outside” and “The Way,” in 2013 and in the video for…