Taylor Swift was ahead of the game when she called out Leonardo DiCaprio for his dating rule of only dating women under 25. In her 2019 album, Lover, Swift's song "The Man" highlighted the sexist double standards in society, using DiCaprio as an example. The song questioned what it would be like if she were a man and boasted about drinking, money, and dating models, just like DiCaprio.

Swift's dig at DiCaprio's dating habits came years before rumors surfaced of him being involved with her best friend, Gigi Hadid. DiCaprio has a reputation for dating younger women, including supermodels and actresses.

While the media and feminists have criticized him, it hasn't affected his fame. However, Swift didn't hesitate to call him out in her song for his alleged playboy persona and the age restrictions he imposes on his romantic partners.

Interestingly, DiCaprio's alleged fling with Hadid adds a new twist to the story. Last year, they were spotted getting cozy in New York, fueling rumors of a relationship. Although nothing has been confirmed, some believe DiCaprio might be willing to break his "under 25" dating rule for Hadid. Swift's callout of DiCaprio's dating habits seems poignant now, as it appears there may be some truth to her critique.