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The Best I Ever Had: The Famous Women Drake Has Dated (PHOTOS)  was originally published on

1. Rihanna


During a concert in Toronto Drake introduced Rihanna by saying, “One more time, if you would do me the favor and make some noise for the greatest woman I’ve ever known in my entire life. She goes by the name of Rihanna.”

Greatest woman he’s ever known? Hmmmm.

2. Serena Williams

Serena Williams

While the couple didn’t make it for the long-haul, Drake told ‘Complex’: “I really, really love and care for Serena Williams. She’s incredible. That’s someone I’m proud to say I know. She’s definitely in my life and I’m in her life. It’s great to watch her play tennis. Very impressive.”

3. Bernice Burgos

Bernice Burgos

While they haven’t ever admitted to ever going out, the couple sure did get close while hanging out on a boat.

4. Tika Sumpter

Tika Sumpter

Tika spilled the beans to “Yes. [laughs] That was one date. The whole cast [of Nickelodeon’s Best Friend’s Date] went out to dinner. He was so nice. And I remember him being like, ‘I’m working on music,’ and he sent me some music, actually. So yeah, he’s been working on music for a long time. And I just remember- I used to call him Aubrey.”

5. Tyra Banks

Tyra Banks

Drake told Ellen DeGeneres: “Jeez. I went on a date with her one time, just one date. We went to Disneyland in disguise, actually, which was fun. I don’t know if it was a date, it was a get-together. We’re close as well.”

6. Kat Dennings

Kat Dennings

When asked about his relationship with Kat, Drake told Ellen DeGeneres: “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.”

7. Zoe Kravitz

Zoe Kravitz

Despite rumors of the two hooking up, Zoe told ‘Complex’ magazine: “I’m very flirtatious…[But] he’s family to me. He’s a really, really awesome dude. We inspire each other…We play each other music.”

We’ll let you be the jury on this one!

8. Maliah Michel

Maliah Michel

Drake met Maliah on the set of his music video for “Find Your Love”.

9. Dollicia Bryan

Dollicia Bryan

Rumors exploded when Drake and another video vixen were photographed looking hugged up together.

10. Karrueche Tran

Karrueche Tran

Drake and Chris Brown’s other ex were spotted partying together. Just friends or friends with benefits?

11. Tatyana Ali

Tatyana Ali

These two have snapped Instagram selfies together and Drake even name dropped her in a song: “The fresh prince, just had dinner with Tatyana, no lie/All these 90’s fantasies on my mind/The difference is that with mine, they all come true in due time”

Did they or didn’t they?

12. Cyn Santana

Cyn Santana

This video vixen is rumored to have been Drake’s girl in 2013.