This study explored interactions between medical residents and patient surrogates in order to clarify resident understanding of roles and relationships, resident emotional experience, and resident learning processes. Qualitative analysis of in-depth interviews were used involving three family medicine residency programs serving culturally diverse, urban, underserved patient populations. Eighteen second- and third-year trainees described a memorable interaction with a surrogate and then were prompted to discuss their learning experience and their role in the interaction. Interviews were transcribed verbatim and analyzed through an iterative process. Residents experienced significant emotional burden during interactions yet continued to value their relationships with surrogates. Despite their reservations about giving recommendations, residents adopted a variety of roles with surrogates as they gave support, information, and advice. Although residents reported little formal education about surrogate decision-making, they relied on passive role modeling and their own previous experiences to help surrogates make decisions. Residents have complex and emotionally significant interactions with surrogates despite minimal formal education about surrogate decision-making. Educational efforts should seek to help residents understand their own emotions and the ethical beliefs that underlie the roles they adopt with surrogates. This will help residents to facilitate value-based conversations with surrogates and better support surrogates in the decision-making process.