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Here I read David Mamet's play Oleanna (1992) with the critical perspectives of Christian theologian Rowan Williams (2000) and political theorist Drucilla Cornell (1995). I argue that each reads the play to trace inadequacies in the framework of sexual dominance that frames the characters’ misbegotten responses to each other. This leads to a critique of an approach to sexual harassment that centers on boundaries or consent. Further, Williams and Cornell each propose conditions of spiritual development that are required to become a political person, which involve protected access to fantasy, desire, and public imagination. With these conditions in mind, I propose themes of reciprocity and play as alternative categories for interpreting what goes wrong in the relationship between the character John and his undergraduate student Carol.