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If you're splitting hairs, she wasn't really a celebrity until that very moment. Teyana Taylor Evidence suggest that Drake and Taylor have a long history.

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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"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.

I think he was talking about wanting to know what my lips taste like and stuff.” After showing the clip, Bow Wow freshened up and got prepared for round two. I went to her crib and kissed her but then she came to my house on a whole ‘nother network and kissed me again.

How many of y’all can say you kissed Tyra Banks twice on the lips?

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… I’m talking family dinners and we in Whole Foods pushing the cart around.Tyra Banks and Bow Wow got people talking this week after they shared a kiss on the music video show 106 & Park.Banks was a guest on the show and host Bow Wow quickly started flirting with the supermodel.The two celebrities haven’t confirmed or denied their relationship but it appears that the romance is strictly for television.Bow Wow and Tyra Banks also kissed on Tyra’s show back in 2009.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.