This article begins with a review of Philip Bromberg’s penultimate psychoanalytic essay, “Sullivan as Pragmatic Visionary, Operationist and OperRelationalist” (2014), in which he honors the founder of the interpersonal psychoanalytic tradition. His focus on Sullivan’s emotional experience—specifically his struggle to be fully himself—reveals both motives and impediments to his interpersonal theory and praxis. The discussion then turns to Philip himself, who—inspired by Sullivan—also privileges the quality of relatedness in the moment, but with a significant difference. Rather than distortions or gaps in reality that impede insight, Philip favors affect, honoring Sullivan’s core notion that the quality of relatedness is central to personal change. Philip’s life both in and out of the consulting room is a testament to this sensibility and is ultimately illustrated in the author’s own experiences with Bromberg as Supervisor, Mentor, and, finally, as Dear Friend.