In the storied romantic comedy, "When Harry Met Sally," Billy Crystal's character famously says men and women can never be friends because "the sex part always gets in the way."

Drake and Serena Williams would beg to differ.

The Canadian rapper, 28, has been spotted all over Wimbledon, hanging out with tons of famous people and watching intently as Williams, 33, won another Grand Slam tournament.


Naturally, Drake's presence sparked rumors of a romance. Williams quickly shot those down.

"We've been friends for, like, so many years," Williams told a reporter after her semifinal victory over Maria Sharapova. "Just like family."

A look at the pair's past reveals that may or may not be true. Drake and Williams have been linked for years, and they're so close that in 2012 Williams' ex-boyfriend, the rapper Common, felt the need to lay down a serious Drake diss track.

Drake and Williams have vacationed together and played tennis together, leading Drake to brag that he can beat Williams "when she's playing with her left."


It's understandable why Common was frustrated. Drake and Williams started hanging out shortly after Common and Serena broke up in 2010. Drake in 2011 had this to say about Williams:

"I really, really love and care for Serena Williams," he told Complex. "She's incredible. That’s someone I'm proud to say I know. She’s definitely in my life and I'm in her life. It’s great to watch her play tennis. Very impressive."

While rumors have died down in recent years as Williams and Drake have been linked with other people, there are still flare-ups which suggest they have feelings for each other. Last year there were reports that Williams and Rihanna, another on-and-off Drake flame, had a confrontation at a Drake concert in Paris.

And even though some have suggested Drake was Williams' Wimbledon good luck charm, the truth is her good luck charm is another man who is likely her boyfriend. Patrick Mouratglou, Williams coach, has guided her to eight Grand Slam titles in 13 tournaments since teaming up.

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