The film follows the story of Drayton “Dray” Jackson (played by Bill Bellamy), a charming and charismatic womanizer who prides himself on his ability to juggle multiple romantic relationships without getting caught. Dray is known among his friends for his “player” lifestyle, which involves dating multiple women and avoiding commitment at all costs.
As the film begins, Dray’s carefree lifestyle is threatened when his sister Jenny (played by Natalia Dyer) becomes engaged and announces her upcoming wedding. Jenny, aware of Dray’s reputation as a ladies’ man, warns him to settle down and find true love before it’s too late.
Determined to prove that he can change his ways, Dray sets out to win back his ex-girlfriend Lisa (played by Lark Voorhies), whom he realizes he genuinely cares about. However, his efforts to win Lisa back are complicated by his own insecurities and the temptations of his player lifestyle.
Meanwhile, Dray’s best friend and wingman, Ray (played by Pierre Edwards), encourages him to continue pursuing other women and avoid commitment at all costs. Ray’s advice leads Dray into a series of comedic misadventures as he tries to balance his desire for true love with his fear of commitment.
In the end, Dray comes to realize that his player lifestyle is empty and unfulfilling, and that true happiness lies in genuine connections and meaningful relationships. He reconciles with Lisa and commits to being faithful and honest with her, embracing the idea of settling down and starting a family.
“How to Be a Player” is praised for its humor, wit, and charming performances, particularly from Bill Bellamy in the lead role. It offers a lighthearted and entertaining exploration of the complexities of modern dating and relationships, as well as the importance of honesty, communication, and genuine connection in finding true love.