This essay considers an instance of medieval fictionality through the devotional text The Life of the Servant by the Dominican Henry Suso, specifically, through an examination of the “Servant’s” attempt to identify with Christ. Two forms of doubleness issue from this attempt, namely, the human servant seeking to embody the divine without remainder and his figuration as sinner and savior. Insofar as the text allows for a play between these polarities, the servant’s devotional practice can be understood as inhabiting the “as if,” or a kind of fictionality. The temptations of a devotional literalism—fiction striving to overcome its fictionality—is portrayed in the Life alongside a vision of devotion that retains the suspensions and play of the fictional.