Friendship, love, and coming of age in New York City, summer of 1994. Luke Shapiro (Josh Peck) has just graduated from high school, sells marijuana, and trades pot for therapy from a psychologist, Dr. Jeffrey Squires (Ben Kingsley). Luke is attracted to a classmate, Stephanie (Olivia Thirlby), who's out of his league and Squires' step-daughter. By July, he's hanging out with Stephanie, taking her on his rounds selling pot out of an ice-cream pushcart. Then things take a turn. In the background, Squires and his wife as well as Luke's parents are having their troubles.