Rihanna and Drake: A Timeline of Their Relationship

It's complicated. In the past six years, Rihanna and Drake have collaborated on four hit songs, performed countless times together, enjoyed dinner dates and, essentially, toyed with our emotions. However, they've never confirmed whether they're officially an item — that is, until the Canadian rapper declared his love for the Barbadian beauty on stage at the 2016 MTV Video Music Awards.

Rihanna accepts the Video Vanguard award from Drake onstage during the 2016 MTV Video Music Awards.
Rihanna accepts the Video Vanguard award from Drake onstage during the 2016 MTV Video Music Awards. Jeff Kravitz/FilmMagic

In honor of that jaw-dropping moment, here's a timeline of the mysterious pair's relationship.

May 2009

A few months after Rihanna's tumultuous split from then-boyfriend Chris Brown, the "Umbrella" singer, now 28, was reportedly spotted cozying up to Drake, now 29, and making out at Lucky Strike, a New York City bowling alley. A year later, Drake referenced the date night on his track "Fireworks," rapping, "I can tell it wasn't love / I just thought you'd f–k with me / Who could've predicted Lucky Strike would have you stuck with me? / Damn, I kept my wits about me / Luckily, what happened between us that night / It always seems to trouble me / Now all of a sudden those gossip blogs want to cover me."

June 2010

Shortly after Drake released "Fireworks," he sat down for an interview with The New York Times, in which he claimed Rihanna treated him like "a pawn." "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," he said.

October 2010

In 2010, the rumored couple released their first ever duet, "What's My Name?," which served as the second single from Rihanna's fifth album, Loud. On the track, RiRi sang, "You're so amazing / You took the time to figure me out." In the accompanying music video, the twosome enjoyed takeout, flirted in a convenience store and sipped white wine. They later delivered a sexy performance of the smash track at the 2011 Grammy Awards.

Rihanna and Drake in the 'What's My Name?' video
Rihanna and Drake in the 'What's My Name?' video

October 2011

More confessions. Drake opened up about his brief relationship with Rihanna in an interview with Elle magazine, saying, "At the time it hurt, but she didn't mean to. I'll never put that on here. I was hurt because I started to slowly realize what it was. I guess I thought it was more. That was the first girl with any fame that paid me any mind."

April 2012

Drake released the music video for his Rihanna-featured song "Take Care" (from his album of the same name), which once again sparked relationship rumors. "I know you've been hurt by someone else / I can tell by the way you carry yourself / If you let me, here's what I'll do / I'll take care of you," she sang on the chorus. In one of the verses, the Degrassi alum rapped, "You don't say you love me to your friends when they ask you / Even though we both know that you do, you do."

June 2012

During a night out at W.i.P. nightclub in New York, Drake reportedly got into a brawl with Rihanna's ex Brown. The "Crew Love" rapper later addressed the incident in an interview with GQ magazine, saying, "Two rappers fighting over a woman — he's not even a rapper, but still. It's the last way you want your name out there. It distracts from the music. But he's made me the enemy, and that's the way it's gonna stay, I guess."

Chris Brown and Rihanna attend a basketball game between the New York Knicks and the Los Angeles Lakers at Staples Center on December 25, 2012 in Los Angeles, California.
Chris Brown and Rihanna attend a basketball game between the New York Knicks and the Los Angeles Lakers at Staples Center on December 25, 2012, in Los Angeles, California. Noel Vasquez/Getty Images

September 2012

Rihanna and Brown reignited their turbulent relationship for a few months in late 2012, causing a rift between the "We Found Love" singer and Drake. At the 2012 MTV Video Music Awards, Rihanna turned her head away and didn't clap when her on-again, off-again beau accepted the Best Hip Hop Video for "HYFR."

February 2014

In an interview with Rolling Stone, Drake opened up about Rihanna once again, saying, "She's the ultimate fantasy. I mean, think about it. Like, 'Man, that would be good.' We have fun together, she's cool and s–t. But we're just friends. That's my dog for life."

November 2015

The "Bitch Better Have My Money" entertainer cryptically told Vanity Fair that her "last real, official boyfriend was Chris Brown." Drake, meanwhile, was linked to tennis pro Serena Williams at the time.

Rihanna, Drake
Rihanna performs with Drake at the 2016 BRIT Awards. Samir Hussein/Redferns

January 2016

Rihanna releases her long-awaited eighth album, Anti, just days after debuting the LP's first single, "Work," which is her third collaboration with Drake. The dancehall song immediately shot to No. 1 on the Billboard charts. In February, she released two back-to-back music videos for the song. In the first, RiRi grinds against Drake; in the second, he lustfully stares at her from a couch as she dances for the camera.

April 2016

Another collab! Drake drops his fourth album, Views, following several delays. The record featured several hits, including "Hotline Bling," "One Dance" and "Pop Style" — but it's the fourth Rihanna duet that got listeners talking. On "Too Good," the pair croon about going out of their way for each other. "I'm too good to you / I'm way too good to you / You take my love for granted / I just don't understand it," they both sing.

Drake presents Rihanna with the Video Vanguard Award during the 2016 MTV Video Music Awards.
Drake presents Rihanna with the Video Vanguard Award during the 2016 MTV Video Music Awards. Michael Loccisano/Getty Images

August 2016

After being stuck in traffic for the majority of the 2016 MTV Video Music Awards, Drake (dashing in a tuxedo) finally arrived just in time to present Rihanna with the Michael Jackson Video Vanguard Award (following her four epic career-spanning medley performances). During his heartfelt speech, the "Controlla" rapper admitted, "She's someone who I've been in love with since I was 22 years old. She's one of my best friends in the world." The adorable moment, which nearly broke the Internet, was followed up by a big hug and a quick kiss from the icon herself.

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