When It Comes Around (2018)

Dexter is a man with all the moves, with the ladies, on the basketball court and in the cutthroat business of sports management. But this player is about to be played. When his company hires a new agent named Jerry and Jerry turns out to be a stunning, competitive woman with moves of her own - Dex will learn a thing or two about relationships and what it feels like to lose. He may just realize that the only way to win is to play from the heart.