In this article, I use the witnessing of a tragic accident and the relationship formed between me, as a first responder, and the victim to describe how in psychoanalysis patients and analysts collide in what Apprey terms “pluperfect errands.” The use of these errands can be an ontological tool in the psychoanalytic relationship and have helped form my identity as a psychoanalyst. Drawing associative links between this story and the analytic dyad, this story travels in and out of tragedy, hopefulness, and repair, resulting in mutual trauma, transformation, and healing, much like what takes place between patient and analyst. I raise the following questions in this paper: Who in analysis is listening to whom? What forms the unique analytic identity? And how does therapy repair the ruptures of previous traumas for both patient and analyst? This paper addresses the inevitable personal and professional entanglements of analysts and details how our histories and haunts are recognized and processed with our patients.