For psychoanalyst Dr. Jeffrey Squires (Ben Kingsley) his sessions with High-School marijuana dealer Luke Shapiro (Josh Peck) ensure a regular supply of pot to the good doctor. Many of Luke's concerns center on growing pains such as finding a girl, and dealing with his parents who are mismanaging their money and losing their upper East-side New York apartment. Squires tells the young Luke to have fun with his youth, find a girl to have a fling with and enjoy the years before he goes to college. To compensate Luke retreats into his own world and deals more pot to rich party kids to earn cash for college.When by chance he meets Dr. Squire's stepdaughter Stephanie (Olivia Thirlby) it seems the two could have a beautiful future together. But Dr. Squires has his own problems of incompatibility with his younger trophy wife Kristin (Famke Janssen). As Luke and Stephanie grow closer, the young man gets advice on how to woo her and Squires, unaware that it is his stepdaughter, goes through a menu of possible ways for Luke to bed the young woman. Luke subconsciously offers Dr. Squires a way to re-experience his own adolescence and during an all-night party the two find themselves arrested for disorderly conduct. Luke returns home to find that he and his parents have been evicted from their house and must move to New Jersey but he and Stephanie go away to consummate their relationship as Dr. Squires and Kristin come together to re-bond their marriage. When things fall apart Luke finds that he has become the one to console the older Dr. Squires in a bitter sweet life lesson.It's the summer of 1994, and the streets of New York are pulsing with hip hop and wafting with the sweet aroma of marijuana. The newly-inaugurated mayor, Rudolph Giuliani, is only beginning to implement his anti-fun initiatives against crimes like noisy portable radio, graffiti and public drunkenness.