The story goes that, way back in 2011, rapper Drake randomly started showing up and supporting Serena Williams at her tennis matches. But in August of that same year, antennas went up everywhere when Drake penned a tweet that read, “I cannot wait to put it on you and make you sweat … during our match this weekend.” Well, alrighty then! Williams, however, was adamant that the relationship the pair shared was strictly platonic. “We’ve been friends for, like, so many years. Just like family,” Williams told a curious reporter in July 2015 when asked about Drake’s attendance at her matches.
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Interestingly enough, however, TMZ caught the so-called platonic pals smooching it up at a fancy Italian restaurant in Cincinnati in late August 2015, only one month after Williams referred to Drake as “family.” But that’s not all. A source told E! News that Drake was definitely in his feelings regarding the tennis legend. “Drake has always had a huge crush on Serena, so he is on cloud nine and will continue to court her as much as he can,” the insider revealed.