Drake and Rihanna: A timeline of their relationship

Speculation over the pair's relationship is at a high sine the VMAs

Rihanna and Drake at the MTV VMAs (Getty)

“Drake and Rihanna Share Kisses, Whispers and Neck Rubs at Miami Afterparty”

“Drake’s Smile Says It All as He Packs on the PDA With Rihanna”

“Drake and Rihanna Kiss Onstage in Miami and the Crowd Goes Wild”

These are the kind of headlines that only Drake and Rihanna could inspire. The relationship status between the two pop powerhouses has remained a bit of a mystery for years.

They have appeared on each other’s albums, they have crazy intense chemistry on-screen and they’ve remained coy about the nature of their connection. They give us just enough to conclude they’re a thing (“She’s someone I’ve been in love with since I was 22 years old,” Drake said at MTV’s Video Music Awards on Sunday), before dialing it back (see: Rihanna awkwardly curving her head when Drake went in for a kiss during the VMAs).

Perhaps their relationship defies any kind of label, but it’s enigmatic enough to keep the public guessing. Here’s a rundown:

When they met

“The first time I met Robyn Fenty, it was 2005. She was shooting a music video at a Restaurant called Avocado in Toronto. The song was ‘Pon de Replay’ and the director of the video was Little X,” Drake said at the VMAs on Sunday night, as he presented an award to the Barbados superstar. “I was introduced to her as a kid who played background music at the restaurant as people ate their dinner. It’s hard to believe that 11 years later all three of us would come together to create the visual for a song called ‘Work.'”

Little X, now known as Director X, told Complex that Drake wasn’t in “Pon de Replay” but that the rapper “grew up in Toronto and knew all those kids” who appeared as dancers in the video.

When did they first *really* meet

In 2009, Chris Brown was charged for assaulting Rihanna, his then-girlfriend. Media attention on the singer’s love life and her relationship status intensified, and it was about this time that Rihanna was reportedly spotted at Lucky Strike in Manhattan with Drake.

Here’s an excerpt from the Page Six item that first fueled speculation about a budding romance between Drake and Rihanna: “‘She was drinking whiskey and apple juice and making out with him all night,’ says a spy. ‘They were really cute together.’ Rihanna, who’s also been spending time in town with Katy Perry, peeled off with Drake at about midnight.”

Drake’s “Fireworks”

The Toronto rapper’s debut album dropped in June 2010, but a couple of songs had leaked on the Internet weeks before. “Fireworks” was among them, and the song addresses his rendezvous with Rihanna and rumors that she felt he had used her for publicity.

Drake says he was a pawn … and then not?

In 2009, Rihanna asked Drake to write her a song, which was never released, but the two began seeing each other regularly, according to the New York Times.

“I was a pawn,” Drake told the Times in 2010 upon his debut album release. “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.”

Weeks later, Drake tried to clarify what he had said, telling MTV News that “in no way was it negative and that she’s “such an overwhelming and incredible person,” but one who “made me feel small. She made me feel nervous.”

“Someone that I was like, ‘I can’t believe I’m here talking to this individual,'” Drake said.

They continued working with each other

Rihanna and Drake collaborated on many projects over the years, and many of those songs played at the possibility or love or something between them. That includes Rihanna’s 2010 “What’s My Name.”

Of the second portion of the video for “Work,” Swedish director Tim Erem told Entertainment Weekly that Drake and Rihanna “are just two friends that are really close to each other. Just put them in front of the camera and that’s what they do. You start recording and the whole chemistry just changed. Everyone’s asking, are they together or they this or are they that? No, they’re friends. They’re just amazing performers and they’re really close to each other.”

This year, Rihanna is very single and very busy

During a February appearance on the “The Ellen DeGeneres Show,” Rihanna was asked about her love life and Drake’s involvement with it.

“I’m single right now,” the singer told DeGeneres, “and it’s not that I’m like, ‘Oh, pro-single, yes, I hate men!’ I just think I have so much on my plate that I can’t even find the time to entertain a steady relationship or anything serious. Or even a text.”

Drake takes out a billboard for Rihanna

Days before Rihanna would receive the Video Vanguard award Sunday, she posted a photo to her Instagram, showing a billboard that Drake had apparently bought out for her. Rihanna’s caption: “When he extra!!” with a trophy and heart emoji.

So buying out billboard space: Is that friend-zone behavior? Relationship behavior? Unreciprocated crush behaviour?

The VMAs

Drake presented Rihanna with the Video Vanguard Award on Sunday, showing up in a tuxedo after he was absent to receive his own award. Here is some of what he said about her:

• “Captivating from day one”
• “When it comes to performance, they swarm in masses just to be in her presence… obviously.”
• “This woman has surpassed all competition while still being the same girl from Barbados, surrounded by the same friends, speaking with the same accent.”
• “Most of all, we love the woman who hasn’t changed since day one.”
• “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.”

Then, Drake handed Rihanna her award and went in for a kiss. It looked like she leaned back, and he planted his lips right on her cheek. It was awkward.

Rihanna did not mention the rapper until the end of her acceptance speech. “Thank you, Drake,” she said, “for that amazing speech.”

Drake posts a couple-like photo

The VMAs had ended, the after parties had begun, and in the early morning hours, Drake posted this very couple-looking photo on his Instagram. Let the speculation continue.

They kiss onstage again

Drake and Rihanna performed Wednesday in Miami, and the crowd goes wild as the two kiss.

Now, it looks like it’s a full, on-the-lips exchange, but it was just quick and obscured enough to continue the post-kiss analysis from Sunday’s VMAs. Let the intrigue continue.

Washington Post.