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    • 2005: Drake & Rihanna’s First Encounter. When Drake stood before the crowd at the 2016 MTV Video Music Awards, he began his speech by talking about the first time he ever met Rihanna.
    • May 2009: First Date. Shortly after Rihanna’s very public 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.
    • November 2009: Rihanna Says She and Drake Are 'Still Friends' 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.
    • June 2010: Drake Realizes Rihanna May Not be That Into Him. While Rihanna believed her relationship with Drake was strictly platonic, Drake seemed to have believed otherwise.
  3. Aug 30, 2022 · October 2016: Drake and Rihanna reportedly have an "open" relationship . A few months after the couple became official, Drake and Rihanna were still going strong.

    • Grace Gavilanes
  4. Oct 11, 2016 · Oct 11, 2016. COMMENT. Image via Complex Original. When Drake confessed his longtime love for Rihanna on stage at the VMAs in August, it was a gratifying moment for many fans. The two were...

  5. May 30, 2023 · Drake, Rihanna, and even Drake's dad can deny the apparent relationship as much as they want, but the photographic evidence has been pretty damning. In 2014, the twosome were spotted in London enjoying a day of shopping, followed by a fancy dinner in Mayfair and an all-nighter at the nightclub.

    • Did Drake have a relationship with Rihanna?1
    • Did Drake have a relationship with Rihanna?2
    • Did Drake have a relationship with Rihanna?3
    • Did Drake have a relationship with Rihanna?4
    • Did Drake have a relationship with Rihanna?5
  6. May 4, 2018 · 4 May 2018. Getty Images. Rihanna's has revealed she no longer has a friendship with Drake. It came as she addressed the time when the rapper publicly declared he was "in love with" her on...

    • Did Drake have a relationship with Rihanna?1
    • Did Drake have a relationship with Rihanna?2
    • Did Drake have a relationship with Rihanna?3
    • Did Drake have a relationship with Rihanna?4
    • Did Drake have a relationship with Rihanna?5
  7. Sep 2, 2016 · Here’s an excerpt from the Page Six item that first fueled speculation about a budding romance between Drake and Rihanna: “‘She was drinking whiskey and apple juice and making out with him all...

  8. Aug 29, 2016 · No photos, but this was the first time that Rihanna and Drake have been linked together romantically. November 2009: Rihanna tells radio personality Angie Martinez during a Hot 97 interview...