Eugene Bell (Zach Cregger) and Tucker Cleigh (Trevor Moore) have been friends since childhood. The lives of the two boys changed completely with their reaction to the Playboy magazine belonging to an older sibling. Through a series of events, this simple act leads to Eugene choosing to lose his virginity at an after prom party to his beautiful girlfriend Cindi Whitehall (Raquel Alessi)i. Unfortunately, all does not go well, and Eugene ends up in a coma. Four years pass, and only Tucker remains at the side of his friend. The hospital bills are mysteriously paid, but there is no sign of life until Eugene gets a knock on the head. The boys discover that Cindi is now the titular Miss March, and take off in search of the intervening years. Madness ensues, as the dynamic duo take off to the Playboy mansion, encountering both sweet and sour along the way.