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In times of extreme polarization, can democracy function? How do we grasp the divisions surrounding us? Does psychoanalysis have anything to offer? The practice of democracy depends on groups and individuals productively engaging with each other around complex issues that are often based in conflicting historical narratives. These are frequently too deeply embedded in group identities to be addressed directly without activating polemical divisions that shut down any potential for negotiation or resolution. The authors describe a psychoanalytically-informed, relational approach to bringing groups together in discourse toward concrete ends through defined projects that can provide a focused holding environment. This, in turn, can foster the interpersonal and inter-group relating essential for working with difference and democratically addressing broader issues within those participating groups. The authors describe ways polarized groups can inhibit the freedom of their members and enjoin them to act undemocratically, the complexities involved in freeing the individual to act both as a member of the group and as a self, and the liberating effects of crossing boundaries between polarized positions. They explore what can occur when suppressed or closely-guarded narratives are shared among groups that don't normally interact with each other, conditions that they have found favor such interchanges, and the unexpected material that can emerge. Using Christopher Bollas' conception of the transformational object, they also explore intersections between individual and group motivations that may either foster or inhibit the work of a project. They conclude with reflections on gauging the efficacy and outcomes of democratically-oriented relational projects pursued within a psychoanalytic frame.