The thesis begins by exploring Stein’s autobiographical connections to the Jamesian concepts of bottom nature and habit, in an attempt to demonstrate that both, in the pen of Gertrude Stein, are as connected to classical virtue theory and the development of character as a moral state and characters as created persons within her creative oeuvre, as they are connected to psychological experiments in William James’ laboratory. In wading through what may seem to be muddy waters of Stein’s slippery definitions and circular sentences, the thesis shows that Stein uses the discourse of classical virtue theory to achieve her goal—breaking down clear barriers to the virtuous life as classically understood and subverting the very building blocks of Western thought generally. Lastly, “Melanctha: Each One As She May” will become a case study through which the thesis wrestles in detail with Stein’s complicated virtue and character project as she pulls virtuous action into a separate sphere from the virtuous person in order to explore what human nature is, or, as she says, “the whole thing about men and women that is interesting.”