El caluroso verano neoyorkino de 1994. Una ciudad gobernada con mano dura por Rudy Giuliani mientras los sonidos del hip hop impregnan también los barrios de los jóvenes blancos. Luke Shapiro (Josh Peck) es un adolescente que vende drogas con la esperanza de resolver la insolvencia de sus padres mientras intenta superar sus problemas de identidad. Toda su cotidianeidad se rompe el día que se enamora de la hija del psiquiatra (Olivia Thirlby) al que vende marihuana a cambio de terapias gratuitas.

Friendship, love, and coming of age in New York City, summer of 1994. Luke Shapiro has just graduated from high school, sells marijuana, and trades pot for therapy from a psychologist, Dr. Jeffrey Squires. Luke is attracted to a classmate, Stephanie, 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.