This paper offers an antiessentialist, psychoanalytic account of gender by arguing against Butler's deconstructive critique of gender essentialism. We develop an alternative to Butler's conception of gender as performative by focusing on those aspects of gender that resist meaning and representation. Using Lacan's concept of the real, we argue that any viable theory of gender must account for the limit conditions of cultural discourses that constitute subjectivity and sociality. Once gender is understood in terms not of proliferating possibilities for meaning, but of a certain impossibility of meaning, then gender's bearing on human relationality requires reconceptualizing. Claiming that various cultural narratives about gender (including traditional psychoanalytic narratives) should be recognized as symptomatic attempts to come to terms with a fundamental impossibility at the heart of sexual difference, we conclude by suggesting ways in which psychoanalysis may productively illuminate the failures of meaning that structure human relationality.