Trust is a fundamental tenet of the patient-physician relationship and is central to providing person-centered care. Because trust is profoundly relational and social, building trust requires navigation around issues of power, perceptions of competence, and the pervasive influence of unconscious bias-processes that are inherently complex and challenging for learners, even under the best of circumstances. The authors examine several of these challenges related to building trust in the patient-physician relationship. They also explore trust in the student-teacher relationship. In an era of competency-based medical education, a learner has the additional duty to be perceived as "entrustable" to 2 parties: the patient and the preceptor. Dialogue, a relational form of communication, can provide a framework for the development of trust. By engaging people as individuals in understanding each other's perspectives, values, and goals, dialogue ultimately strengthens the patient-physician relationship. In promoting a sense of agency in the learner, dialogue also strengthens the student-teacher relationship by fostering trust in oneself through development of a voice of one's own.