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Donnel Stern and I met in the spring of 2016, when I was a fourth year candidate at the New York Psychoanalytic Institute. He had begun teaching a new course there in interpersonal and relational psychoanalysis. I soon became fascinated with the contrast between the relational perspective and the classical one; the latter was more familiar to me from my education and training. In the years since, Don served as discussant in a clinical case presentation, and I have participated in a weekly study group he leads. More importantly, he functioned as one of several, crucial interlocutors that helped shape my development as a psychoanalyst. I came to understand his perspective further through an in-depth, critical study and consideration of his own work, mine, and that of others and came to count on him as a friend and colleague. What follows is a rather wide-ranging discussion between Don and me about his views and experiences as a psychoanalyst. It begins with an exploration of aspects of his life that affected his outlook on the profession of psychoanalysis, and then moves into a discussion about the nature of the practice itself. In the process, I expressed my own related but somewhat distinct views. Our conversation ventured freely into the meaning of each of our own experiences as psychoanalysts, with the hope that this may be of interest in thinking about psychoanalysis more generally. No part of the discussion is prescriptive regarding what psychoanalysis or a psychoanalyst should be. Our hope is that the interview provides an important articulation of Don’s unique theoretical perspective, but in a fashion that remains approachable. What follows is simply a discussion between two people from different backgrounds who found a way to explore a variety of significant ideas with one another.