Drake and Rihanna: a timeline
What a coincidence: once again, Rihanna has a new album to promote, and once again the tabloids are buzzing about a possible romance between her and Toronto hip-hop superstar Drake. The pair recently recorded a duet that will appear on Rihanna’s upcoming album. Plus, she’s showing up at his concerts and making sure that the paparazzi are there every step of the way. To which we say, Come on, Drake—didn’t you learn your lesson the last time? Here, a brief history of their rocky relationship.
May 2009: Rihanna is spotted smooching a mystery man at an L.A. bowling alley; said MM turns out to be Aubrey “Drake” Graham. At the time, People mag described him as “an actor…best known for playing wheelchair-bound Jimmy Brooks on Degrassi.” Oh, what a difference a year makes.
May 2010: By the time his album Thank Me Later is released, Drake is the new king of the bling set and BTFs (that’s best thugs forever) with L’il Wayne, Kanye, Jay-Z, Eminem and Alicia Keys. Still, if the lyrics on his song “Fireworks” are any indication (“I can tell it wasn’t love, I just thought you f**k with me… What happened between us that night, it always seems to trouble me. Now all of a sudden these gossip rags wanna cover me”), it’s obvious he’s still hung up on the girl that got away.
June 2010: Drake vents to the NY Times about his time spent under Rihanna’s umbrella: “I was a pawn. You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, wow, this feels terrible.”
September 2010: Well, look who’s come crawling back. It seems Little Miss Fierce hasn’t fared so well since giving Drake the cold shoulder pad. Her last album, Rated R, was a critical and commercial flop; meanwhile, his career has blown up bigger than Suzanne Rogers’ beehive. So is it any wonder she’s looking to re-establish their relationship? Walk away, Drake. We swear, you’ll thank us later.
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Courtney Shea is a freelance journalist in Toronto. She started her career as an intern at Toronto Life and continues to contribute frequently to the publication, including her 2022 National Magazine Award–winning feature, “The Death Cheaters,” her regular Q&As and her recent investigation into whether Taylor Swift hung out at a Toronto dive bar (she did not). Courtney was a producer and writer on the 2022 documentary The Talented Mr. Rosenberg, based on her 2014 Toronto Life magazine feature “The Yorkville Swindler.”
