When: August 2011

After being snapped hitting a Florida resort to play tennis together, Drake was rumored to be doing a little something-something with tennis star Serena Williams. Drake was also spotted cheering on Serena when she played (and won) the 2011 Rogers Cup in the rapper's hometown of Toronto. Then a clip of Serena twerking it to Trey Songz's "Bottoms Up" in Drake's condo surfaced. Grand Slam winner turned video vixen? Drake would later deny and say that it was not his place.

Smash Probability: She definitely helped him practice some type of stroke.