A comprehensive guide to Drake and Rihanna’s are-they-or-aren’t-they romance

Can these two just make it official already? <3 <3 <3

By Erin Cook

So, did you see Drake profess his undying love for Rihanna ON STAGE at the VMAs? Basically, Drizzy told the whole world that he’d been in love with Ri Ri since he was 22-years-old. (Considering he’s now 29, that’s quite some time.) At one point, it even looked like Drake was going to drop down on one knee and propose.

The whole scene got us thinking: Are they secretly dating or aren’t they? This isn’t the first time we’ve speculated about their relationship status. In fact, rumours have been flying since 2009. Let’s take a walk down memory lane to when it all began:

May 2009
According to Page Six, Drake and Rihanna were spotted K-I-S-S-I-N-G at Luck Strike Lanes & Lounge bowling alley in New York. One onlooker also noted that Ri Ri’s choice of drink for the evening was whiskey and apple juice. The pair left together at about midnight. ~StEaMy~

November 2009
During an interview with Hot 97, Rihanna insists that she and Drake are just friends. “We just went out — my friends, his friends,” she said. So… do you, ah, kiss all your friends like that Ri Ri? June 2010
Drake was so touched by their rendezvous that he wrote a verse about Rihanna in his song ‘Fireworks.’ He says: I could tell it wasn't love, I just thought you'd fck with me Who could've predicted Lucky Strikes would have you stuck with me? What happened between us that night it always seems to trouble me*

That month, he also gave an interview to The New York Times, telling them that Rihanna treated him like a pawn. Yikes. “You know what she was doing to me?” he said.” 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.”

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Drake soon changed his tune though. In an interview with MTV News, he said:
"She's just such an overwhelming and incredible person and such a talented person, and someone that I was like, 'I can't believe I'm here talking to this individual,' that she just gave me that feeling like when I was 17 years old trying to take Nikki Ramos, this girl from Toronto, out on a date and she never wanted to go with me. She never would go; she would have a million excuses why she couldn't talk to me. That's how [Rihanna] made me feel, she made me feel small; she made me feel nervous. It just put me back to the Acura in Toronto, feeling like Aubrey Graham, not Drake."

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October 2010 The pair obviously put their differences to the side, releasing ‘What’s My Name’ together.

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February 2011
Drizzy and Rihanna put on a racy display at the Grammy Awards while performing ‘What’s My Name.' VERY racy.

April 2012
Bad gal Ri Ri and Drake collaborate on ‘Take Care,’ the title track for Drizzy’s new album. Their chemistry in the accompanying film clip in glaringly obvious.

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During an interview with MAX Choice FM, Drake gushes about Rihanna like it’s NBD, saying that he loves her. "I think that we have a connection that's established for life and that is that I love her and support her unconditionally, and I like to think that she feels the same way,” he said. “Do I fancy her? Of course, I mean who wouldn't? Look at her, she's stunning. Of course I do. Yeah, no, she's incredible. But you know, it's one of those things that it's a maybe one day, maybe not."

June 2012 Trouble in paradise. Rihanna briefly got back together with Chris Brown (noooooo!), sparking a bar fight between their respective entourages. Apparently, Chris sent Drake a bottle of champagne as a peach offering but he wasn’t having a bar of it. According to reports, Drizzy sent it back with a note that read, “I’m still f*cking Rihanna.” BURN!

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April 2013 During a radio interview, Drake explained his beef with Chris Brown. Apparently, it was because, “At one point in life, the woman he [Chris Brown] loves fell into my lap.” Again, BURRRRN!

May 2013 Chris and Rihanna break it off… again. Drizzy does a victory dance in private. (Probably.)

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August 2013 Ooh la la – the pair were spotted enjoying a quiet dinner for two before the MTV Video Music Awards. Meaning they’re back on? Or…?

September 2013
Drake appeared on the Ellen Degeneres Show, prompting the talk show host to ask whether the two had ever dated. "Yeah, great girl,” he said. “We had our moment and you know, I mean, always support and have love for her.” So that’s PAST tense? February 2014
While speaking to Rolling Stone, Drizzy had absolutely no chill. "She's the ultimate fantasy,” he said. “I mean, I think about it. Like, 'Man, that would be good.' We have fun together, she's cool and shit. But we're just friends. That's my dog for life."

According to Page Six, Chris Brown’s rep alluded to the fact that Drizzy and Ri Ri are back on. He said that, “[Chris] is focused about his recovery. He only wants the best for her and is happy that she found someone.”

April 2015
Drake and Rihanna were spotted gettin’ close (read: kissing) at Coachella. So… they’re back on? Onlookers seemed to think they looked couple-y.

November 2015
Ri Ri FINALLY speaks up about the romance. In an interview with Vanity Fair, the singer says that her last “real, official boyfriend” was Chris Brown.

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January 2016 Undeterred by Rihanna’s blasé comments, Drake collaborated with the popstar for ‘Work’.

February 2016
The film clip drops for ‘Work’ and oh my god, WHY AREN’T THESE TWO PUBLICLY DATING YET?!!

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Later that month, Rihanna tells Ellen that she’s “single right now.” Rihanna, please. Do you even believe yourself?

Also in February, Drake puts a picture of Ri Ri on the wall of his restaurant in Toronto.

April 2016
Bad gal Ri Ri kindly invited Drake on stage during her Anti World concert to perform ‘Work.’ Safe to say, there was a lot of grinding and twerking and sexually charged eye contact between the two. Drizzy paused to tell the audience, “One more time, if you would do me the favor and make some noise for the greatest woman I've ever known in my life. She goes by the name of Rihanna.”

May 2016
Drizzy gives yet ANOTHER interview about how wonderful Rihanna is. Yes Drake, she’s wonderful, you love her etc. He tells Beats 1 Radio, “We do well together as a team… I think [the chemistry] is what makes the records better, though. It's something genuine there. We're not forcing some story on people. A lot of the music that we make and the energy that we bring is genuine. We have a lot of genuine energy between us.”

During an appearance on the Ellen DeGeneres Show, the host throws a picture of one of their ~sexy~ performance on screen and asking Drake what the story is. He says, “That's friendship at its finest right there.” Because who DOESN’T grind up on their friends?

June 2016
Drake performs with Rihanna again during her Anti World tour. This time, in Manchester. He tells the crowd, “Shout out to the most beautiful, talented woman I've ever seen. She goes by the name of Rihanna… I'm getting my heart broken.”

Did y'all see that? 👀@drake 💋 @Rihanna 😍#ANTIWorldTour Manchester 🎈 pic.twitter.com/cpczdQQhMh

August 2016
Aaaaaand that should bring us up to the present. While up on stage at the VMAs, Drake poured his heart out to the ENTIRE WORLD, saying: The first time I met Robyn Fenty was 2005. She was shooting a music video at a restaurant called Avocado in Toronto called "Pon De Replay" and the director of the video was lil x. I was introduced to her as a kid who played background music at a restaurant as people ate pasta. It's hard to believe that 11 years later, that all three of us would come together to create visuals for a song called "Work". Today, the world knows Little X as Director X, they know me as Drake and not the kid singing while you order pasta. But 11 years later, they still all know Rihanna as the one and only Rihanna. Captivating from day one, the iconic being that is Rihanna was already at a place that most artists only dream of going. For them that is often the peak, but for her that was the starting point that she has kept to ascending to an untouchable level ever since. When it comes to music she relentlessly takes over the charts with every release. When it comes to performances, they swarm in masses just to be in her presence, obviously. And when it comes to fashion and style, she makes it seem so effortless, until you try and do it yourself, which is when it gets a little awkward. What's most impressive isn't the endlessness of stats, awards, and accomplishments. What's most impressive is the person. Some artists need to play a character to achieve success; some need to downplay their own natural instincts to blend in. She succeeds by doing something no one in this industry does, which is being herself. This woman has surpassed all competition while still being the same girl from Barbados surrounded by the same friends, speaking with the same accent and never missing a Crop Over unless it's to come perform at OVO Fest. We love the music, which can change styles from album to album. We love the videos, which change their artistic vision from year to year. But most of all, we love the woman who hasn't changed since day one. She's someone...she's someone I've been in love with since I was 22 years old, 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.

Let's just ignore that ~AwKWaRd~ moment when Rihanna dodged Drake's kiss after he presented the award. Probably not the reaction he was hoping for.

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