Martin (Phifer) has spent his life being a good son, a good brother and a good friend, but his luck with women is all bad. The softly spoken art columnist hasn't had a date in three years since losing his fiancée to bi-curiosity and when he meets Paula (Miller), the pretty young art professor who lives upstairs, Martin's lack of experience is all too apparent. Enter brother Junnie (Andre B. Blake), an expert in scamming and scheming. This ultimate 'player' intends to teach Martin how to get any woman he wants.

Sporting a new look and attitude, Martin is becoming a regular Casanovaias he spends every night on the prowl with Junnie. But it isn't long before reality closes in. A missed deadline places his job in jeopardy, he's losing the respect of his best friend, and worst of all Paula is under the impression that he's a womanizer. Do nice guys really finish last? Is responsibility a blessing or a curse? And when is being a player just too much work?