This study applies recent theories about humor to a sample of talk among a group of young adults about the issues and problems associated with homelessness. In this conversation, participants demonstrate a pattern of joking and language play that expresses a complex and ambivalent set of attitudes and feelings toward homelessness and toward the homeless as both outcasts and refugees from conventional society. Humor is used both to express complex responses to homelessness and as a tool for managing the tone and direction of the conversation. The results demonstrate how the identification of patterns of joking and wordplay can provide insights into how people accomplish task-oriented objectives as well as relational and interactive objectives in everyday talk.