Using data from both qualitative interviews and quantitative questionnaires from 32 undergraduate resident assistants (RAs) at a private, residential university, this study explored RAs' role conflict derived from their simultaneous positions as rule enforcers and friends, vis-a-vis their residents. Most RAs reported that they were friends with some residents on their own floors, at least occasionally experienced role conflict when handling residents' policy violations, and had difficulty taking disciplinary action against residents with whom they were more familiar. These findings have implications for RAs' training and roles that involve changes to the residential life office's organizational structure and processes. (Contains 3 tables.)