The foundations for a strong and compassionate doctor–patient relationship are crucial aspects of family medicine training. While the benefits of a good alliance between physician and patient are well known, the doctor–patient relationship may not develop effortlessly. The process of medical education can negatively impact physician empathy and therefore can adversely affect the bond between a clinician and patient. The medical system itself may have negative effects, as physicians must contend with the push to see more patients, focus on metrics, and struggle to advocate for patients against third-party payors. This chapter explores ways in which training programs can implement efforts to enhance the doctor–patient relationship. Stressing the importance of communication skills and practicing interactions with simulated patients is part of the experience. However, integrating medical humanities is a useful tool that utilizes various genres to introduce concepts and challenge the learners to develop skills that cement the doctor–patient bond. Residents learn self-reflection, appreciate the patient’s perspective, and balance emotion with professionalism as they master empathy. Teaching young physicians how to build strong doctor–patient relationships can open fresh opportunities in the traditional medical curriculum, engaging both the learner and instructor.