Whether we can expect others to listen—and whether we choose to listen to others—have become central challenges in handling conflicts around polarized and high-profile political matters. For those who study alternative dispute resolution (“ADR”), these concerns about listening hit especially close to the bone because they implicate some of the most foundational precepts of dispute resolution practice. This paper explores some of these implications in the context of the fight over reproductive rights, with special focus on the “listening dilemma” that people experience when navigating extremely difficult conversations around crucial political entitlements, especially when those entitlements are in the process of being made and unmade. Paying closer attention to the listening dilemma and other unusually challenging dynamics in public conflicts makes plain the importance of social context when deciding what interventions may be applicable or appropriate. As it turns out, these interventions include listening—but not as dogma and only to the extent that listening makes sense, given goals and context.