In dialogical self theory (DST) authenticity has not been a central concern. The humanist notion of a static, higher-order, superordinate, ultimate, and “true” self runs counter to the ontology of DST, and the conceptualization of the dialogical self as unconsolidated, multifaceted, dynamic, and sensitive to situational change. In a climate in which the psychology of authenticity is undergoing revision—and in which the existence of a “true” “inner” self is increasingly questioned—it is these qualities that make DST highly suited to the investigation of authenticity in contemporary life. Four aspects of DST can facilitate the exploration of authenticity: (1) the function of personal positions and their role in shaping and stylizing social positions, (2) how I-positions differ in relation to openness to innovation and the degree to which they are personally endorsed, (3) how I-positions can encompass a shared identity and can express a collective voice, and (4) the emotional tenor of experiences involving authenticity. To illustrate the utility of this conceptual assemblage, a case study of the authenticity experiences of an early-career language teacher is presented. The study demonstrates how, in the dialogical self, authenticity involves the experience of how one is in one’s actions and in one’s relationships.