Purpose: Medical student empathy and character changes are of great interest with clear implications for patient interactions. With much focus on deleterious education culture, this study focuses more on what may bolster empathy and character. Building from interventions highlighting role models, the authors hypothesize the importance of informal relational connections within medical school may promote both modest empathy and character development. Materials and Method: This study uses unique secondary data that follows a cohort of medical students over time, with two surveys about a year apart. The data is unique not only in the inclusion of time, but also in various relational measures and both a medical-specific empathy as well as a general empathy measure. This allows for modeling change in medical student empathy. Results and Conclusion: First, general and medical-specific empathy appear to function different. At baseline, receiving positive character feedback from an attending/resident is positively related to medical empathy while negative feedback is inversely related to medical empathy and burnout is related only to general empathy. Over the next year, being around an admirable physician increased both types of empathy, seeing burnt out specialists increased medical empathy, and a sense of calling generally bolsters empathy. Second, exposure to morally admirable role models is broadly, although modestly, related to character development. It is positively associated with expectations for faculty to teach, shape, and train character, and with an increased sense that bad people may not make good physicians. Finally, exposure to these role models tends to increase one’s sense of calling to the profession. While not dramatic, informal relationships can be an important part of professionalization and may affect general and medical-specific empathy differently, and shift changes in student character.