"She's someone I've been in love with since I was 22 years old," Drake, 29, told the crowd. "She's one of my best friends in the world. 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."
The pair then exchanged a sweet, if slightly awkward, kiss, leaving fans guessing again: Are they or aren't they a couple?
Speculation about their relationship dates back to 2009 when they were first spotted making out over bowling balls and whiskey and apple juice at New York City's Lucky Strike Lanes & Lounge.
Here's a quick history of Rihanna and Drake:
A few months after the Lucky Strike sighting, Rihanna told DJ Angie Martinez that she and Drake were just friends.
The following year, Drake acted like a spurned lover, writing a verse about Rihanna in his song "Fireworks" and telling The New York Times that she treated him like a pawn after he wrote a song for her and it never got released.
"I was a pawn," he said. "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.'"
By the year's end he had gotten over it. The pair released "What's My Name?" and made a steamy video together.
After a hot performance of "What's My Name?" at the Grammys, Drake and Rihanna were caught canoodling at a Canadian nightclub a few months later.
Drake confessed to Rolling Stone that Rihanna is his "ultimate fantasy" and was later seen traveling through Paris with her. Once again the romance was short-lived.
Whatever Drake was feeling for her, Rihanna made it clear to Vanity Fair's November issue that Brown was her last real, official boyfriend.
When Drake dropped his own album a couple months later, featuring their collaboration "Too Good," many fans believed the song was about them.
After Sunday's VMAs, the pair were seen drinking and dancing at an Los Angeles nightclub. Drake wasn't done praising Rihanna either. He posted a selfie on Instagram of the two of them, writing, "This is a night for us all to be thankful for what you have done for us! You have affected so many of our lives in the best way possible. Tonight we celebrate you!"