The ladies love Drake. He’s been an in-demand bachelor since his days as Wheelchair Jimmy on “Degrassi.” Girls would be throwing themselves at the charismatic, talented, & biracial Drake even if he weren’t a megastar. Indeed, he has quite the dating record, and in light of his most recent girl, Serena Williams, we take a look at some of his more high-profile relationships over the years.


Serena Williams

10 Celebrities Drake Has Dated

Drake and Serena’s cozy restaurant session last night was the first time they’d been seen together since this year’s Wimbledon, where an onlooker reported, “it’s pretty obvious that they are together.”

Common started his 2011 beef with Drake over Serena, which would indicate that they have been on-and-off for sometime. “Me and Serena was together,” explained Common. “We broke up. I don’t know specifically her and Drake, it felt like obviously something was going on [after we broke up], I ain’t dwell on it too much. I ain’t have no problem with that, you do what you do. After a while I felt like in some of Drake’s songs he was saying stuff that was subliminal to me.”

Rihanna

10 Celebrities Drake Has Dated

Rihanna and Drake were romantically involved in 2009 and 2010, back when they were stars but not yet megastars. Their break-up hit Drake pretty hard. “You know what she was doing to me?” he said in a 2010 interview with the NY Times. “She was doing exactly what I’ve done to so many women throughout my life, which is show them quality time, then disappear,” he said. “I was like, wow, this feels terrible.”

Said Rihanna: “It was a really fragile time in my life, so I just didn’t want to get too serious with anything or anyone at that time.”

Though they’ve never officially gotten back together, they seem to reunite occasionally for steamy nightclub sessions.

Tyra Banks

10 Celebrities Drake Has Dated

“I went on a date with her one time, yeah,” said Champagne Papi. “We went to Disneyland in disguise actually, which was fun.”

Cat Washington

10 Celebrities Drake Has Dated

Reality TV addicts know Cat Washington from “Bad Girls Club,” a show similar to “Flavor of Love” but minus Flavor Flav. Drake met Washington in 2009 on the set of “Best I Ever Had” and dated her for a year.

“It was an awesome relationship,” said Washington looking back. “I was in love, he was in love and by the way in the song he said he was in love, so don’t try to switch it up now… It was good. I’m talking family dinners and we in Whole Foods pushing the cart around. It was a regular relationship.”

Zoë Kravitz

10 Celebrities Drake Has Dated

Though Kravitz says that she and Drake (whom she calls “Aubrey”) are simply “very good friends,” they have appeared canoodling on both of their Instagram accounts and were spotted making out at a Beyonce concert in 2013.

“Zoë Kravitz is like one of my favorite people in the world,” said Drake in 2011.

Bernice Burgos

10 Celebrities Drake Has Dated

Not long after dropping If You’re Reading This It’s Too Late, Drizzy was photographed in Australia kissing the 34-year old Bronx bottle waitress. If you’re splitting hairs, she wasn’t really a celebrity until that very moment. Now she’s a successful Instagram model.

Teyana Taylor

10 Celebrities Drake Has Dated

Evidence suggest that Drake and Taylor have a long history. She posted pictures of her and Drizzy sharing kisses on her MySpace (!) in 2009, and they reunited for a cozy Instagram photo in 2013. “Fuck all ya’ll niggas…except my niggas…meet the exception. #DayOne,” he wrote. 

Keshia

10 Celebrities Drake Has Dated

Keshia Chanté

The former “106 & Park” host dated Drake when they were around 14 years old. She’d just moved to Toronto from Ottawa to work on her music career and he was also in the entertainment industry, on Degrassi, fresh off his bar-mitzvah.

Kat Dennings

10 Celebrities Drake Has Dated

“I just always had a huge crush on Kat Dennings and she was kind enough one night to oblige me and we went out for dinner,” said Drake. “They don’t call me back after one date according to this.”

Dollicia Bryan

10 Celebrities Drake Has Dated

After being romantically linked to the likes of Bow Wow, Jamie Foxx, & Maino, the model dated Drake for a month in 2011. But it was never meant to be.