Drake and Rihanna: A History of Their Relationship

Drake told the VMA audience that he's been in love with Rihanna for years.

ByLuchina Fisher
August 29, 2016, 1:44 PM
PHOTO: Drake escorts Rihanna after presenting her with The Video Vanguard Award during the 2016 MTV Video Music Awards at the Madison Square Garden in New York, Aug. 28, 2016.
Drake escorts Rihanna after presenting her with The Video Vanguard Award during the 2016 MTV Video Music Awards at the Madison Square Garden in New York, Aug. 28, 2016.
Jewel Samad/AFP/Getty Images

— -- Drake and Rihanna sent their fans into a frenzy Sunday night when he presented her with the Michael Jackson Video Vanguard Award and not only declared his love for her but sealed it with a kiss.

"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.


Things got complicated after Chris Brown re-entered Rihanna's life. Both men seemed to be vying for her attention. Brown collaborated on Rihanna's track "Birthday Cake" and she collaborated with Drake on "Take Care." That June, the tension boiled over when a bar brawl broke out between Brown and Drake's crews. In the end, Brown won over Rihanna and the couple reunited from Sept. 2012 to May 2013.


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.


Romance rumors returned full force this January when Rihanna released her smash single "Work," featuring Drake. Their steamy performance of the song at February's Brit Awards certainly did nothing to quell the rumors.

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!"

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