Psychoanalysis has endeavored to provide innovative and creative methods of navigating and understanding human experience. But the very theoretical innovation that once opened new pathways of understanding can become, over time, an intrusion into the fluid nature of clinical practice and thought. In this paper I follow the evolution of a treatment relationship when, after the death of a young patient, I was faced with a desire to remain connected to members of the patient’s family. Available theory offered little help in my effort to navigate this unchartered territory. I examine outer edges of psychoanalytic experience, and consider how the field might evolve to potentially embrace relationships that don’t reflect traditional psychoanalytic conceptualizations.