Despite agreement that teaching on professional boundaries is needed, the design of health profession curricula is challenged by a lack of research on how boundaries are maintained and disagreement on where boundaries should be drawn. Curricula constrained by these challenges can leave graduates without formal preparation for practice conditions. Dual role or overlapping relationships are an example: they continue to be taught as boundary crossings amidst mounting evidence that they must be routinely navigated in small, interconnected communities. In this study, we examined how physicians are navigating overlapping personal (non-sexual) and professional relationships with the goal to inform teaching and curricula on professional boundaries. Following constructivist grounded theory methodology, 22 physicians who had returned to their rural, northern and/or remote hometown in British Columbia, Canada or who had lived and practised in a such a community for decades were interviewed in iterative cycles informed by analysis. We identified four strategies described by physicians for regulating multiple roles within overlapping relationships: (a) "signalling" the appropriate role for the current context; (b) "separating" roles by redirecting an interaction to an appropriate context; (c) "switching" roles by pushing the appropriate role forward into the context and pulling other roles into the background; and (d) "suspending" an interfering role by ending a relationship. Negotiating boundaries within overlapping relationships may involve monitoring role clarity and role alignment, while avoiding role conflict. The enacted role regulation strategies could be critically assessed within teaching discussions on professional boundaries and also analyzed through further ethics research.