Rihanna's first liason with Drake came in the aftermath of her infamous February 2009 beating at the hands of Chris Brown. Three months later, in May, Rihanna and Drake were spotted hooking up at Lucky Strike, a Manhattan bowling alley. According to Page Six, “She was drinking whiskey and apple juice and making out with him all night… They were really cute together.”
The were spotted together several times over the course of the 2009. Around the time Rihanna started dating baseball star Matt Kemp, in November 2009, she gave an interview with Angie Martinez in which she denied having ever dated Drake. “Me and Drake are still friends actually,” she said. “[We hung out] a few times but no, never."
“People thought I was dating Rihanna…" Drake said in a January 2010 interview with XXL. "That was semi-true."