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Uncanny similarities between Dante's conception of afterlife and Freud's conception of psychic structure are discussed with respect to how both men envisioned the trajectories of desire and the abstractions of time in spatial terms. How psychoanalysis works in relation to Freud's picture of psychic structure is shown to parallel how Dante's Purgatory functions in relation to the poet's architecture of the afterlife. Drawing on Freud's letters to Fliess during the years on either side of Freud's first trip to Orvieto, this paper hypothesizes the possibility of a less uncanny and more fraught ancestral connection between these cartographers of man's soul.