6. Keshia Chante
Singer and radio host on 106 & Park Keshia must have caught Drake’s eye back in their early careers. Actually, these two cuties first got into a relationship when they were just 14 – all together now: awwww! She came to Toronto to work on her music career and he was working on Degrassi in the city, and the rest was history. It seems that the relationship continued until they were a little older, with Keshia and her mother even getting a reference in Drake’s “Deceiving,” and Keshia doing vocals for him on “Fallen” in 2012. He says he’s proud to call her an ex-girlfriend.
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