Ariana Grande and Mac Miller have broken up, TMZ reports. Miller and Grande had been dating since 2016. Pitchfork has reached out to both artists’ representatives for comment.

The two frequently collaborated on music together. Grande is featured on “My Favorite Part” from Miller’s 2016 album The Divine Feminine. That same year, Miller was featured on a remix of her single “Into You.” Grande’s Yours Truly single “The Way” features Miller. During her 2017 benefit for victims of the bombing at her Manchester concert, Miller made an appearance.

When Grande released her new single “No Tears Left to Cry” last month, Miller shared a message of support. “very proud of this girl right here ❤️,” he tweeted. “Welcome back. We missed you. One of a kind.”