The Wackness (2008)

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.