A Timeline of Rihanna & Drake’s Complicated Relationship

From steamy collaborations to public outings, Rihanna and Drake toyed with fans’ emotions for years, constantly sparking speculation as to what the status of the pair’s mysterious relationship or friendship was.

The term “just friends” came up often when Rihanna and Drake were coaxed into discussing their relationship. But in a 2018 profile for Vogue, Rihanna made their status crystal-clear when she said they were no longer even friends.

Of course, since then, Rihanna has gone on to romantically partner up with a different musician, A$AP Rocky, with whom she shares two children: 1-year-old RZA and baby Riot Rose, born in August. Now, with the release of Drake’s For All the Dogs album, fans are speculating that the rapper is taking shots at Rihanna and Rocky on some of the songs, particularly “Fear of Heights,” “Virginia Beach” and “Another Late Night.”

On “Fear of Heights,” Drake repeatedly says the word “Anti” — the title of Rihanna’s most recent album — and asks: “Why they make it sound like I’m still hung up on you?” On “Virginia Beach,” he seemingly references her new relationship, rapping, “Drawin’ conclusions like you got a Parsons degree or somethin’/ I coulda treated you better, that’s crazy.” (Rihanna has an honorary degree from Parsons School of Design.) On “Another Late Night,” Drake seems to take aim at Rocky. “I ain’t Pretty Flacko,” he raps, nodding to Rocky’s nickname, “Bi— this sh– get really Rocky.”

Two years before Rihanna proclaimed the end of their friendship, Drake had stood on the 2016 MTV Video Music Awards stage to present Rihanna with the Video Vanguard Award and professed his love for the Anti singer for all the world to hear. So where did it all go wrong?

Below, Billboard takes a look back at Rihanna and Drake’s history.