A critical component to instituting compassionate, patient-centered diabetes care is the training of health care providers. Our institution developed the Family Centered Experience (FCE), a comprehensive 2-year preclinical program based on longitudinal conversations with patients about living with chronic illness. The goal of the FCE is to explore the experience of illness from the patient’s perspective and ultimately to incorporate this perspective in clinical practice. In this qualitative study, we wished to investigate the impact of “diabetes stories”—the stories of FCE volunteers with diabetes—on medical students’ understanding of diabetes and its management. Individual interviews were conducted with medical students who had worked with a volunteer with diabetes to answer the questions: “in what ways was learning through these ‘diabetes stories’ different from that acquired through lectures and textbooks,” and “how did these stories impact the students’ understanding of diabetes and its care?” Thematic analysis of the transcribed interviews was performed using Grounded Theory. Several major themes emerged: There was more to diabetes than the “scientific” knowledge acquired through lectures; the stories challenged students’ assumptions about having or working with people with diabetes and allowed students to see the world through the perspective of someone with diabetes, and the stories motivated students’ development as physicians and influenced their general perspectives of doctoring and medicine. First-person narratives of living with diabetes allow for learning in affective, experiential, and cognitive dimensions, stimulate self reflection and perspective-taking, and enhance growth through the challenging of previous assumptions, beliefs, and perspectives. This type of learning is transformative and may result in a shift in students’ perspectives towards more open, inclusive attitudes towards patient-centered diabetes care.