Approaches to learning and teaching cast under the designation of “relational pedagogy” provide the focus of this chapter. We argue that democratic education is most apparent in the moment of encounter between students and teachers. When deliberative negotiation of learning occurs and recognition is given to the mutuality of the pedagogical encounter, moves toward a democratic education are established. For this pedagogic deliberation to occur, the formation of meaningful relationships between students and teachers is fundamental. By meaningfully coming into relation and setting about the task of negotiating how learning should proceed, teachers and students give credence to the immediacy of the moment—to the immediacy of the pedagogical encounter—and the effects exerted by the context within which this relationship is activated. This chapter asserts that it is in these terms that relational pedagogies actively resist the normalising effects of dominant expressions of schooling typical of this present moment—approaches to schooling that preface reductive, decontextualised, “one size fits all” logics—to instead provoke recognition of the idiosyncratic, in-the-moment character of learning. It is in these moments that deliberation and negotiation become crucial to learning and expose formations of a democratic education that positions the relational at its core.