The film begins with Woody Watson (Michael Rainey Jr.) having a dream about him and his mother in the woods, but he then wakes up. Woody lives with his grandmother (Lonette McKee) in the inner city of Baltimore and longs to be reunited with his mother who is in rehab in North Carolina. His charismatic Uncle Vincent (Common) has recently returned home after eight years in prison determined to straighten out his life by opening a high-end crab shack. Vincent drops Woody off at school, but when Woody becomes embarrassed when a girl looks at him, Vincent decides to give the boy a tutorial on how to become a man.