Drake and Serena Williams sparked dating rumors between 2011 and 2015, with their relationship leaving lasting impacts on pop culture and music.

The pair's connection first became public when Drake frequently attended Serena's tennis matches in 2011, even posting suggestive tweets about playing matches with her. Their relationship seemed to intensify in 2015 when paparazzi caught them kissing at a Cincinnati restaurant after one of Serena's matches.

Drake referenced their relationship in several songs, including "Worst Behavior" where he rapped about playing tennis at his home. Another track, "Nothings Into Somethings," is believed to address Serena's marriage to Reddit co-founder Alexis Ohanian in 2017.

The story took an interesting turn during 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 critical of Drake.

While neither Drake nor Serena has officially confirmed their past relationship, their history continues to influence pop culture discussions and music references, demonstrating how their brief connection left a lasting impact on both sports and entertainment worlds.

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