8. Teyana Taylor
Drake definitely likes to hold on to his women for a long time, often going back to old flames for another round, and Teyana is no exception. It seems that their history dates back to 2009 and beyond, when she posted photographs of herself kissing Drake on her MySpace page. Just the fact that it was on MySpace should give you an idea of how long ago this all was! They also appeared close in an Instagram photograph posted in 2013, in which Drake appeared to hint at a relationship with the caption. We don’t know the full story here, but there’s clearly water under the bridge.
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