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This article challenges traditional approaches to gender difference in prescriptive negotiation analysis. Historically, dispute resolution scholars and practitioners analyzing the determinants of gender have either assumed or concluded that women and men negotiate differently, with so-called “women’s ways” being seen as less effective than “men’s ways” at achieving principled negotiation results. This position has led scholars to offer prescriptive negotiation advice that maps onto two forms of difference feminism: liberal feminist negotiation (translatable as “fix the woman”) and cultural feminist negotiation (translatable as “fix the system around the woman”). This article critiques difference feminist theory for its practical and political implications in principled negotiation. These criticisms suggest that difference feminist theory limits the range of negotiation tools accessible to everyone by reinscribing sex and gender stereotypes, and only allows room for feminist interventions based in minoritizing discourses of female/feminine bargaining identity at the expense of universalizing discourses of human activity. The article then offers an alternative based in postmodern feminism, “protean negotiation,” that aspires to dissolve fixed gender identities for the practical and political benefit of both women and men. This article concludes by suggesting that a form of the classic Negotiator’s Dilemma is reflected in the progressive politics of gender in negotiation where cultural feminism and postmodern feminism suggest a tension between ideological commitments to “identity” and “activity” respectively. These intuitions give rise to a struggle called the “Feminist Negotiator’s Dilemma,” and there may be no way to resolve it. The task for progressive politics should be to accept these competing imperatives and to negotiate their contradictions if feminists are to effectively understand, let alone resist, the limitations of gender difference in negotiation theory and practice.