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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.
  1. 23 Apr 2012

    455M views

  2. Aug 30, 2022 · A timeline of the on-and-off romance between Drake and Rihanna, from their first meeting in 2005 to their breakup in 2018. See how the stars collaborated, flirted, and fought over the years.

    • Grace Gavilanes
  3. Feb 20, 2021 · Drake and Rihanna have collaborated five different times throughout their careers. The pair last collaborated in 2016 on the fan-favorite song "Work." We've ranked all five of the artists'...

  4. Oct 11, 2016 · From kissing in 2009 to fighting in 2012, Complex chronicles the years of on-again, off-again relationship between Drake and Rihanna. See the milestones, the songs, the videos, and the quotes that shaped their connection.

  5. Dec 19, 2019 · The official audio of "Too Good" (feat. Rihanna) by Drake.Follow Drakehttps://drakeofficial.comhttps://facebook.com/Drakehttps://instagram.com/champagnepapih...

    • 4 min
    • 5.7M
    • YM Entertainment
  6. Feb 20, 2024 · A detailed recap of how Drake and Rihanna met, dated, collaborated, and fell out over the years. From their first kiss in 2009 to their feud in 2018, see the ups and downs of their complicated history.

  7. Aug 31, 2016 · Read on to take a walk back through Rihanna and Drake's romance, from the "Pon de Replay" video, to their many tantalizing collaborations, to their make-our-hearts-go-bum-bum-be-dum moment...