This dissertation examines the social function of literature for Oprah’s Book Club (OBC) in comparison to how Dave Eggers’s imagined audience approaches his fiction and nonfiction. By comparing these two groups of ideal readers, this project explores how certain reading communities understand reading and authorship to relate to therapeutic culture, self-transformation, social awareness, and, in some cases, social engagement. Understanding “therapy” broadly to mean the effort to transform oneself in response to emotional or physical distress, this project builds on scholarship which argues therapy sits at the heart of many contemporary approaches to literature. When reading therapeutically, literature is a tool used to understand the self in relation to others and in response to current events. Reading selections of work by Jonathan Franzen and Dave Eggers as well as engaging with episodes of The Oprah Winfrey Show and OBC discussions, this project explores how OBC and Eggers encourage their ideal audiences to improve themselves therapeutically by reading in similar but distinct ways. OBC and Eggers similarly direct their ideal audiences to transform themselves while reading by identifying with a work’s author or characters. Likewise, they similarly believe literature holds the potential to inspire social awareness and a sense of social responsibility for their respective literary communities. For OBC, however, readers benefit from books by connecting literary works to their authors’s biographies to identify with however an author seems to improve him- or herself by writing. In contrast, Eggers’s writing encourages its ideal readers to reject the importance of Eggers’s biography to his work in favor of identifying with his narrators and protagonists as discrete people separate from Eggers. By identifying with Eggers’s characters rather than with Eggers himself, Eggers’s texts encourage his imagined audience to understand his characters’ problems as their own, pushing his ideal readers to improve themselves by becoming more empathetic, socially aware people. In comparing these two literary communities, this project explains how OBC’s and Eggers’s approaches to literature share a belief in literature’s self- and socially transformative potentials despite encouraging readers to improve themselves while reading by identifying with different aspects of literary work.