It was the fourth night in a row that the Canadian rapper has partied into the early hours with his rumored flame Making music: Rihanna and Drake collaborated on Work for Rihanna's latest effort Anti and Too Good featured on Drake's album Views with a source telling E!News that the music sparked attraction between them On Wednesday, according to reports, he'd told the crowd at Manchester's Emirates Old Trafford stadium, as he introduced her for a surprise guest appearance: 'Shout out to the most beautiful, talented woman I've ever seen. Drake -- who also bought a billboard sign for Rihanna ahead of her MTV honor and later shared a kissing selfie of the two -- only had eyes for the "Love On the Brain" singer at a VMA after-party at Up & Down nightclub, a source told ET. "They walked in together and never left each other's side all night," the source said. Earlier this year, Drake and Rihanna starred in the supersexy music video for their song "Work," and the rapper has popped up on stage with the sexy singer at a handful of her concerts to help perform the hit.It wasn't long before rumors swirled that the former couple could be giving things another try, and most recently, the pair heated things back up after they put on quite the lovey-dovey show at the MTV VMAs, with Drake revealing that he's "been in love" with Rihanna since he was 22 years old.
May 2009: Rihanna and Drake are allegedly spotted making out at Lucky Strike in Manhattan, as reported by , who discloses that their source spotted Rihanna “drinking whiskey and apple juice and making out with him all night.” No photos, but this was the first time that Rihanna and Drake have been linked together romantically. August 2016: Ahead of the MTV Video Music Awards, where Rihanna is receiving the channel’s Vanguard award, Drizzy decides to declare his well-documented affection for her to the world by taking out a billboard congratulating her. ” which is probably the most apt statement anyone could make about Drake’s affection.At the MTV VMAs, Drake presents Rihanna with her Video Vanguard Award; in his speech, he bares his heart to both her and the VMA audience, revealing that he is in love with Ri Ri.“She’s someone I’ve been in love with since I was 22 years old. All my adult life, I’ve looked up to her even though she’s younger than me.” After delivering this heartfelt and highly vulnerable sentiment, Aubrey Drake Graham boldly attempts to passionately kiss Rihanna, at which point, she curbs him and allows him to chastely kiss her on the cheek."I was introduced to her as the kid who played background music at the restaurant as people ate their dinner." "She's someone I've been in love with since I was 22 years old," he later gushed, prompting big cheers from the audience. All my adult life, I've looked up to her, even though she's younger than me.She's a living, breathing legend in our industry." And the flirtiness between the two didn't stop there.