Sometimes it's right to do the wrong things.

During the summer of 1994, New Yorker Luke Shapiro (Josh Peck) has just graduated high school. Now faced with three hot months in the city before going off to college, Luke spends the time dealing pot, listening to hip hop and exchanging his wares for therapy sessions with psychiatrist Dr. Squires (Ben Kingsley). Luke is also infatuated with his popular and beautiful classmate Stephanie (Olivia Thirlby), who is also hanging around Manhattan for the summer and just happens to be Dr. Squires' step daughter. As the long days idle by, Luke begins to build two of the most important relationships of his life.