Drake’s Trying Way Too Hard To Impress Rihanna! Ottawa, ON, Canada / JUMP! 106.9 August 26, 2016 11:38 pm Rihanna will be receiving the Michael Jackson Vanguard Award this Sunday at the VMAs and this is how Drake congratulated her. When he extra ❤🏆!!! A photo posted by badgalriri (@badgalriri) on Aug 26, 2016 at 3:43pm PDT So are you guys dating or what?