Mr. Shoot His Shot: All the Women Drake Has Famously Flirted With

The girl of your dreams is probably not a challenge to him.

By Jasmine Grant

Drake has never been coy when it comes to the women he’s interested in. In fact, he damn near campaigns to make sure his celebrity WCW’s know exactly how much they mean to him. How can a girl not feel flattered?

Considering the magnitude of his celebrity, Drake could, in theory, have any curvaceous Instagram model beauty within his reach. So his ability to actively pursue one girl with laser-like precision and make her feel like the hottest thing since cooked food must be applauded. Whether it’s on wax, in person, or on a t-shirt, Drake is always super suave when it comes to flirting. Honestly, truly…it’s why we love him.

It’s time for you “Netflix and chill” connoisseurs to whip out those notepads and take some cues from the 6 God on how flatter a lady. Take a look at all of famous women Drake has flirted with. Trust us, you’ll learn a thing or two.

  • Rihanna

    Drake and Rihanna have a much deeper history than the other ladies on this list. The two pop stars met on the set of Rihanna’s breakout video/single “Pon de Replay” and have collaborated (on and off screen) for years since. He even went to war with Chris Brown over her, so you know this is more than a crush. While presenting her with her MTV Video Vanguard Award, Drake let the “L” word loose and proclaimed that he is in love with the Bajan pop star. There wasn’t a dry eye in the house. Now the question is…are they in this for the long run?

  • Doris Burke


    Drake was pretty bold in his attempts to court ESPN reporter Doris Burke. I mean, the kind of bold that gave him the idea to wear a “Women Crush Everyday” shirt featuring her picture at the Raptors vs. Warriors game in November, which also happened to be “Drake Night.” When asked about his adoration for the 51-year-old sports analyst, I think she is a stunning woman, incredible at what she does. I wish she was here tonight, just sending my love to her. I love Doris with all my heart, so hopefully she knows she’s woman crush every day.” Moments later, Doris tweeted Drake to confirm their dinner plans were on. Clealy, there’s no shame in Drizzy’s game – and it works!

  • Taylor Swift

    Getty Images

    Yes, we were just as confused about this one as you are. Last month, Drake posted an Instagram photo of himself and T. Swift with their backs to the camera, captioning it “Is that velvet?” (a famous line from the classic comedy Coming To America, if you’re not proficient in pop culture one-liners.) The photo was taken at Drake’s birthday party, prompting rumors that the two were dating. “Seeing Taylor Swift in person is always fun for me,” Drake told Extra. “I just have this small little thing with her; I just like her whole being. I’m excited about her career.” Since then, we haven’t heard much about these two aside from chatter that a song collaboration could be in the works. For now, the possibility of Drake and Taylor actually becoming a thing appears to be in our rear view.

  • Serena Williams

    Serena is headstrong and focused on winning, but still isn’t impervious to the charms of Toronto’s own. The two were spotted exchanging tons of PDA at a NYC restaurant. And although we loved the possibility of these two hooking up, they’re both enjoying the single life and aren’t quite ready to give that up. There may also be a little thing called “Rihanna” standing in the way of this.

  • Nicki Minaj

    *Sigh.* Though obvious rifts (*cough Meek Mill cough*) have driven these two apart, there was a time where nothing and no one could stop Drake from getting Nicki on his arm. Drake has devoted several verses to his pursuit of his label mate, and although Nicki thought only innocently of their playful exchange, it seemed to us Drake was really hot on making Nicki his lady. There’s still hope for you yet, Drake. If not, at least you can think back on the good times…like that ’Anaconda’ lap dance.

Watch VH1 staffers narrate Drake and Rihanna’s relationship timeline in the video below.

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