Drake and Serena Williams' relationship has been a subject of speculation since 2011, when the rapper began regularly attending her tennis matches. Their connection first gained public attention after Drake's playful tweet to Serena about making her "sweat" during a match.

In 2015, their relationship appeared to intensify when paparazzi caught them kissing at a Cincinnati restaurant following one of Serena's matches. However, neither party officially confirmed their romantic involvement.

Drake's music has featured several apparent references to Serena. In "Worst Behavior," he mentions tennis matches, while "Nothings Into Somethings" is believed to address their relationship's end, coinciding with Serena's 2017 marriage to Reddit co-founder Alexis Ohanian.

The story took an interesting turn at Super Bowl LIX in 2025. Serena made a surprise appearance during Kendrick Lamar's halftime show, dancing to "Not Like Us" – a track widely considered to be a Drake diss track.

While neither Drake nor Serena has ever publicly confirmed their past relationship, their interactions over the years – from courtside appearances to musical references and public events – have kept fans and media speculating about their true connection. Serena has since built a family with Ohanian, while Drake continues to reference past relationships in his music.

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