Relationships between patients and psychiatrists are shaped by a complex array of factors. The clinical experience centers on diagnostic and treatment decisions occurring in the context of a structured relationship that is regulated by principles of professional ethics and personal boundaries. At the same, however, patients and psychiatrists are unique and autonomous agents with emotional responses to one another that may evoke a wish for a personal friendship or other sorts of personal relationships that are outside the bounds of the usual professionally defined structures. Negotiating the tension between the need for professional regulation and the desire for developing a friendship with certain patients can present clinical and ethical challenges in psychiatric practice. Pragmatist reasoning can help the psychiatrist and patient to successfully negotiate the dilemma that may arise when either or both of them wishes to develop a personal friendship but still adhere to the ethical tenets of the patient/psychiatrist professional dyad.