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A History of Drake and Rihanna's On-Again, Off-Again, Maybe Sort-Of Romance
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Part 9: Wow, Maybe You Guys Should Just Confirm This Sh*t Already

  • August 2016: Drake brings Rihanna on stage with him at his annual OVO Fest in Toronto. While introducing her, Drake says, "You showed up two nights in a row for my city. You might have to go half on a baby," adding, "This is the greatest entertainer in the world, flying all the way in from God knows where . . . and looking good doing it too." Despite their romantic aquarium date days later, sources report that the couple "haven't made their relationship official" because Rihanna is pumping the brakes. "Drake would make her his girlfriend in a second if he could. It's more on Rihanna, though. They both care about each other and are having a good time spending time with each other," a source told E!. A few weeks later, ahead of Rihanna receiving the Michael Jackson Video Vanguard Award at the MTV VMAs, Drake does the unthinkable: he buys the singer a billboard in LA to offer his congratulations. We can't even get a text back. On VMAs night, after being "stuck in traffic," Drake hops on stage to present Rihanna with her Vanguard award. During his speech, Drake admits that he's "been in love with" Rihanna since he was 22 years old, adding, "She's one of my best friends in the world." He goes in for a kiss before the two leave the stage holding hands. Later that night, Drake posts a snap of him smooching the singer via Instagram, writing, "You have affected so many of our lives in the best way possible. Tonight we celebrate you!"
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