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Drake

The rapper and Rihanna have a complicated history, going back years. They had a short-lived romance in 2009 — a little too short for Drake — which prompted him to tell the New York Times that he felt used by Rihanna. (He later clarified that he didn’t mean for his comments to come across as negative.) They continued to be flirty together — both on and off the stage — and Rihanna ex Chris Brown seemed to be at war with Drake for a while. By 2016, Drake and RiRi seemed like they might be dating again, with her kissing him at his concert in full view of everyone and his gushing about her while presenting her with the Video Vanguard Award at the 2016 MTV VMAs. “She’s someone I’ve been in love with since I was 22 years old,” he said. Think they’ll ever get back together? (Photo: Kevin Mazur/WireImage)

Rihanna's romances, including Hassan Jameel, Chris Brown, Drake, and more of her romantic history

Raechal Shewfelt
Editor, Yahoo Entertainment

Rihanna has, as she sings, found love in a hopeless place — and more than once. The “Love on the Brain” singer — who turns 30 on Feb. 20 — has romanced musicians, athletes, and singers, a number of whom are famous themselves. Take a look back at the notable loves of the star’s life so far.