This thesis is made up of one half of a novel, titled The Yearning Sessions, and a long fiction story, titled "Lifestory: A Memoir." Though different in both form and content, these fictions share a number of thematic investigations: explorations of new masculinities in American culture, fabular and fantastical figurations of the Midwest region, and the artistic convergence of the theoretical concepts of memory and haunting. Though relegated concertedly to the realm of fiction, or fantasy, even, these writings also contain a pointedly autobiographical character, meant to imbue the work with honest, if purposefully baroque, emotional resonance.