Drake Is Just Saying Rihanna Can Do Better Than Hassan Jameel (REPORT)

2009

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](https://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."

2010

In an interview with the [New York Times](https://www.nytimes.com/2010/06/13/arts/music/13drake.html?r=0)_, Drake revealed Rihanna treated him like a "pawn," and apparently used him to get over her relationship with Chris Breezy.

“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.

2011

The couple quickly reignited relationship rumors following their sultry performance of "What's My Name" at the 2011 Grammy Awards.

In July of the same year, TMZ reported the ~couple~ were spotted "snuggling up at a private booth" at a Canadian nightclub.

2011

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.”

2013

Following Rihanna's collaboration on Drake's "Take Care," the rapper continued to open up about the island beauty during an interview with Ellen DeGeneres in September.

"Yeah, great girl," he told the talk show host. “We had our moment. Always support and have love for her and yeah…”

2014

After her brief reconciliation with Chris, Drake, not one to mince words, confessed that Rihanna is his "ultimate fantasy" during an interview with Rolling Stone.

“I mean, I think about it,” he said. “Like, 'Man, that would be good.’ We have fun together, she’s cool and sh-t. But we’re just friends. That’s my dog for life.”

2015

During an interview with Vanity Fair, Riri revealed her "last real, official boyfriend" was Chris, and seemingly shut down any rumors of a previous relationship with the Toronto rapper.

“I am going to do what makes me feel happy, what I feel like doing," she said.

2016

Rihanna debuted her first single "Work" from her Anti album in February — featuring, of course, Drake. Riri later drops the video for the track, and there's no denying the pair's chemistry.

In March, Rihanna embarked on her Anti World Tour, with the rapper making a few appearances throughout. The pair couldn't keep their hands off each other while on stage.

2016

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.

2016

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.