In "The Wackness," we meet Luke Shapiro (Josh Peck), an 18-year-old youth who just graduated from high school. The film is set during the summer of 1994, where hip-hop music is starting to become the new thing and something Luke is a huge fan of. In order to make money so he can enjoy his summer, Luke sells weed while posing as an ice cream man. Although he's gradually becoming an adult, there's one thing Luke hasn't done yet; lose his virginity. In his quest to lose his innocence, Luke takes advice from Dr. Squires (Ben Kingsley), a middle-aged psychiatrist who gives Luke free advice in exchange for free weed. Luke becomes taken with Stephanie (Olivia Thirlby), Dr. Squires step-daughter who's around the same age Luke is. Although Luke thought she was way too out of his league, Stephanie returns the affection and the two embark on a summer of self-discovery.