In his Thank Me Later cut “Fireworks,” Drake comes to the realization that his feelings for her were far stronger than her feelings for him. While Rihanna believed her relationship with Drake was strictly platonic, Drake seemed to have believed otherwise. Speaking to Martinez, Rih shut down the rumors and revealed that she likes “hot and older” men and insisted that she and Drake were “still friends.” Martinez continued to press Rihanna about a possible romantic relationship brewing between the two artists, but Rihanna continued to deny there ever being a romance.ĭrake Realizes Rihanna May Not be That Into Him – June 2010 Rihanna stopped by Angie Martinez’s radio show to discuss her headline-grabbing breakup with Chris Brown and address the rumors that she was dating then- 90210 star Tristan Wilds and Drake. Rihanna Says She and Drake Are “Still Friends” – November 2009

Sources told the outlet that Rihanna was “making out with him all night.” ?Shortly after Rihanna’s very public and calamitous split from Chris Brown in 2009 after Brown’s assault of the singer, Page Six reported that Drake and Rihanna were spotted at Lucky Strike in New York City. Rihanna was shooting the music video for “Pon De Replay” at a restaurant in Toronto and was introduced to Drake, who “played background music at the restaurant as people ate their dinner.” History has a way of repeating itself because the same director, Director X, who worked on Rihanna’s “Pon De Replay” video, also directed Drake and Rihanna’s “Work” video years later.

When Drake stood before the crowd at the 2016 MTV Video Music Awards, he began his speech by speaking about the first time he ever met Rihanna. So where did it all go wrong? We may never know.īelow, Billboard takes a look back at Rihanna and Drake’s history.ĭrake and Rihanna’s First Encounter – 2005 Nearly two years ago, Drake stood up on the 2016 MTV Video Music Awards stage to present Rihanna with the Video Vanguard Award and professed his love for the Anti singer for all the world to hear.

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