The Daily Grind Video

1. Rihanna

BRIT AWARDS 2016 - The Show Source:Getty

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 (USA) vs Belinda Bencic (SUI) Source:Getty

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

Drake And Bernice Burgos In Perth Source:Splash News

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

Essence 9th Annual Black Women In Hollywood - Arrivals Source:Getty

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 Source:Getty

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

2016 Pre-GRAMMY Gala And Salute to Industry Icons Honoring Irving Azoff - Arrivals Source:Getty

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 Source:Getty

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

'Chocolate City' - Los Angeles Premiere Source:Getty

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

9. Dollicia Bryan

Pharrell Williams Qream Launch Party Source:Getty

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

10. Karrueche Tran

2016 Daytime Emmy Awards Nominees Reception Source:Getty

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

11. Tatyana Ali

BET AWARDS '14 - Red Carpet Source:Getty

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

VH1 'Love & Hip Hop' Season 4 Premiere Source:Getty

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