Drake and Rihanna first started dating in 2009, four years after they first met (she was filming the video for “Pon de Replay,” and he was DJing at a Toronto restaurant). This is arguably Drake’s biggest and most significant long-term relationship. After then, the romance grew stale. In 2010, Drake admitted to The New York Times, “I was a pawn.” You are aware of what she did to me, right? She was treating them with the same respect I’ve shown so many ladies throughout my life by spending time with them before vanishing. Wow, this feels awful, I thought.
For the next ten years or so, Drake and Rihanna’s relationship would come and go. Once again together in 2010, they broke up in 2011. Rhianna rekindled her relationship with Drake in 2016 after her 2010 affair with Chris Brown.
“We adore the videos, which have a yearly shift in aesthetic direction. In his unexpected performance at the 2016 MTV Video Music Awards, Drake said, “But most of all, we love the woman who hasn’t changed from day one. Drake gave Rihanna the Vanguard Award for that year, describing her as “one of my greatest friends in the world” and “someone I’ve been in love with since I was 22 years old.” Despite the fact that she is younger than me, I have looked up to her my entire adult life. She’s a living, breathing legend in our industry.”
However, the passion dwindled once more, and it was finished by Spring 2017. “The most difficult thing was definitely waiting through that [MTV VMAs] speech.” “I don’t enjoy getting too many compliments; I don’t like being put down,” Rihanna told Vogue in 2018. “We’re not friends anymore, but we’re also not enemies.” That’s all there is to it.”
Drake had his own personal crisis in 2018, thanks to Pusha T disclosing Drake’s hidden child. Rihanna had already moved on with Hassan Jameel at the time. Rihanna welcomed her first kid, a bay boy, with father A$AP Rocky in May 2022.