Drake & Rihanna — See Pics Of The Couple Together

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February 27, 2014 8:16AM EST

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Drake and Rihanna

Drake and Rihanna — Friends turned collaborators turned lovers, Drake and Rihanna, first met in 2005. Rihanna was shooting the music video for “Pon De Replay” at a restaurant in Toronto at the time, were she was introduced to Drake. The two became good friends, but it wasn’t until her 2009 split from Chris Brown that they went on their first date. The pair released a number of collab tracks through the years, including “Work,” “Take Care,” and “What’s My Name.” However, things seemed to go south between Drake and Rihanna after the 2016 MTV VMAS when Drake gave an over-the=top speech that nearly overshadowed Riri’s moment in the spotlight that night. Rihanna later admitted that she was “uncomfortable” during his speech. While the two on-again, off-again friends aren’t currently on speaking terms, you can take a walk down memory lane and see all of their best photos together by clicking through the gallery.

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Rihanna twerks On Stage With Drake

Rihanna twerks On Stage With Drake — Rihanna wears a sheer bodysuit as she twerks on stage with Drake during a performance of their hit single “Work’. It took place at the American Airlines Arena in Miami, Florida.

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Drake & Rihanna on Stage

Drake & Rihanna on Stage — Rihanna, left, and Drake perform at the 53rd annual Grammy Awards on Sunday, Feb. 13, 2011, in Los Angeles. She rocked a fierce red outfit during their number.

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Drake & Rihanna At VMAs

Drake & Rihanna At VMAs — Drake presents Rihanna with the Video Vanguard Award at the 2016 Video Music Awards. She graciously accepted after he showered her with compliments.

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Drake Helps Rihanna Off Stage At The 2016 MTV VMAs

Drake Helps Rihanna Off Stage At The 2016 MTV VMAs — Drake, right, helps Rihanna leave the stage at the MTV Video Music Awards at Madison Square Garden in New York. He had presented her with the Vanguard Award.

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Drake & Rihanna Performing

Drake & Rihanna Performing — Rihanna surprises the crowd at Drake’s concert in Toronto. The pair performed a duet together and showed off their dance moves while entertaining the crowd.

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Drake & Rihanna Nearly Kiss Onstage

Drake & Rihanna Nearly Kiss Onstage — Drake and Rihanna hit the stage for a performance at his 7th Annual OVO Fest. The two nearly shared a kiss as they grinded on each other.

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