This lesson uses Deborah Ellis’s short story “Through the Woods” as a catalyst for conversation around questions that are useful in examining the impact of cannabis use and regulation on individuals and relationships. “Through the Woods” is about a day in the life of Matthew, a 14-year-old boy who buys cannabis at school to take to his ailing grandmother who raised him until she became too sick to care for him. The story is ripe with easy-to-see themes that young people are sure to question naturally and/or identify with (e.g., stereotypes about cannabis dealers, users and non-users; risks and rewards of selling/buying/using cannabis; and reasons for using). As such, the story can be used to help students develop their skills in asking good questions as they interact with a story and its characters in more complex ways. This lesson aims to deepen students’ understanding of relationships between peers, family members and others as well as the complex nature of human drug use.