Did Drake & Serena Williams Actually Date? There Was Definitely A Flirtation There

Now that Drake is rumored to be dating Rihanna yet again, let us not forget that brief and wonderful moment in 2015 when it looked like Aubrey Drake Graham managed to snag another woman way, way out of his league: one of the greatest athletes of all time, miss Serena Williams. But did Drake and Serena William ever really date? Like with Rihanna, there's only conjecture, but in one writer's opinion, Drake and Serena Williams definitely had something going on.

Drake and Williams have actually been friends since 2011. And Drake is confident enough in himself that he actually gets on the court and plays tennis with Williams, which is quite a bold move. In the fall of 2011, the pair started hitting the tennis court together and the first rumors about the rapper and the tennis great being linked started spreading. Drake playfully added a little fuel to the fire on Twitter, writing in August 2011, "@serenawilliams I cannot wait to put it on you and make you sweat..........during our match this weekend." Damn, keep it clean, people!

Rumors then settled down for a few years — until last summer, when Drake was ever-present courtside at all of Williams' matches at Wimbledon. And the video below should be proof enough that the two of them were, like, totally smitten. Those smiles are enough to make the Grinch's heart grow three sizes.

In August 2015, according to TMZ, the two made out at a restaurant in Cincinnati. Sure, mackin' on someone doesn't mean that you're dating, but I want to believe that tender Drake and the greatest athlete of our time once had a love that was real, though brief.

And who was it that was sitting front row at Williams' runway show during New York Fashion Week in September 2015? Anna Wintour, of course. Oh, and next to her, look who it was: Aubrey Graham. And to make things even more suspicious, Williams played Drake's music throughout her showing for her collection HSN Signature Statement.

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Williams and Drake never confirmed their relationship, because that would be too risky. Never admit to anything if you're famous is what I assume is the law of the land. Williams was asked about their potential romance at a press conference at Wimbledon in July 2015. According to Entertainment Tonight, a reporter asked if Drake was her "lucky charm." Drizzy, who was there reportedly "laughed and put his face in his hands," and Williams apparently rolled her eyes and said, "We've been friends for like, so many years. Just like family." But do you make out with your family?

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I would like to believe that Drake and Williams were once honestly in love, or at least getting there. But I am also superstitious, and for me, I feel like #BlameDrake is what ended their relationship. In September 2015, Drake cheered Williams on from the stands during the U.S. Open.... which she lost. I'm not saying that Williams blamed Drake, but everyone else did. And not long after, Williams started dating someone else... a Redditor. That really had to hurt Drake when she started publicly dating Reddit co-founder Alexis Ohanian in October, just after Drake's 29th birthday, too.

So even though it was never really confirmed, the facts that are there are satisfying enough for me. But even if it was just a flirtation, their love sadly did not last... Unlike Williams' domination of the tennis world, because she can't be stopped, and she won't be stopped.