The purpose of this chapter is to extend and elaborate two closely linked arguments from the previous chapter. The more local of the two arguments concerns a reading of the intellectual tradition within which Chaucer developed his interests in gender and sexuality and his sense of those interests as central to a project of philosophical poetry. The larger of the two arguments concerns the recovery of a medieval idiom for understanding psychological phenomena such as repression, fetishism, narcissism, sadism, and masochism. The two arguments dovetail in a resistance to taking either set of concerns as distinctively modern, or as requiring a modern conceptual apparatus such as psychoanalysis to understand. Rather than turning to speculative biology, traumatic narrative, any of the various developmental models of the psyche, or any of the various psychic topographies advanced by Freud or Lacan, my argument focuses on the perennial link the Christian tradition has made between problems of sexuality and problems of autonomy, a link which, as Peter Brown has argued, was central to Christian thinking about morality and sociality from Paul to Augustine, and which remained so throughout the Middle Ages and beyond. Partly to indicate the differences between the place of sexuality in this tradition and in psychoanalysis, in the previous chapter I bracketed sexuality completely, arguing that a sufficiently supple reading of dialectical form in Boethius's Consolation of Philosophy both provides a philosophical account of repression and fetishism and leads to the conclusion that agency is constitutively masochistic.