Drake and Rihanna were first reported as an item back in 2009. Following the demise of Riri's highly publicized relationship with Chris Brown, AubRih was spotted at an NYC bowling alley flaunting major PDA. According to [Page Six](http://pagesix.com/2009/05/20/rihanna-takes-a-strike/?ga=1.62434924.1725247282.1386617566)_, Rihanna was “drinking whiskey and apple juice and making out with him all night.”
Drake seemingly addressed this encounter in his song "Fireworks" with the line, “Who could’ve predicted Lucky Strikes would have you stuck with me/What happened between us that night it always seems to trouble me."
“I was a pawn,” Drake confessed. “You know what she was doing to me? She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear. I was like, 'Wow, this feels terrible.'”
The two eventually cleared up any bad blood, and collaborated on the track "What's My Name" a few months later.
In October 2011, Drake opened up about the short-lived romance during an interview with Elle magazine.
“At the time it hurt, but she didn’t mean to,” he said of their breakup. “I’ll never put that on her. I was hurt because I started to slowly realize what it was. I guess I thought it was more. That was the first girl with any fame that paid me any mind. You spend days reading about this person in the magazines."
He continued, "All of a sudden you have this number one song and you’re at some birthday party and there she is. And you’re just some naïve kid from Toronto staying in some sh-tty ass hotel who got invited to this party on a whim. That’s just how it happened.”
In August, ahead of the VMAs, Drake surprised Rihanna with a billboard after she was chosen to be the recipient of MTV's Michael Jackson Video Vanguard Award. Riri shared the photo via Instagram, and her caption hinted she and Drake were very much back on.
During the 2016 VMAs, Drake professed his love to her just before presenting her with the Vanguard award, "She's someone I've been in love with since I was 22-years-old. She's one of my best friends in the world."
She later thanked him for the heartfelt words via Instagram.
Shortly after the VMA's, Rihanna made a surprise appearance at Drake's sold-out concert in Miami. After her performance of "Bitch Better Have My Money," the two shared a sweet kiss just before embracing.
In September, Rihanna debuted a small, camouflaged shark tattoo on her ankle; the rapper appeared to have the same tattoo inside his right arm during his Summer Sixteen tour.
The whirlwind affair was once again short-lived, as reports in October revealed the couple had split. Drake has since been connected with singer Jennifer Lopez.