In this chapter, Megna complicates Slavoj Žižek’s analysis of the undead, masochistic nature of courtly love by examining how the courtly lover’s masochism always carries with it an implicit threat of mutating into sadism. Whereas Žižek, following Jacques Lacan, attends to courtly love’s basis in a masochistic libidinal economy in which the Lady is an inaccessible, inhuman partner (a “Thing”) who tasks the courtly lover with impossible demands that are radically incommensurable with his needs and desires, Megna instead attends to works of medieval literature—above all, Geoffrey Chaucer’s Troilus and Criseyde—in which the courtly lover’s masochistic, servile disposition toward the Lady is wont to transform into sadistic hate on a whim. As Megna contends, what works such as Troilus and Criseyde demonstrate is that the libidinal economy of courtly love is always already sadomasochistic in nature, dependent on two distinct yet nonetheless interrelated modes of privileged male enjoyment.