In this article, I offer an example of confronting a certain kind of “deadness” through an ongoing case with an adolescent who suffers from a chronic disorder that often manifests itself in fluctuating states of severe depression, psychotic anxiety, and debilitating dissociation. I intend to demonstrate that, through an understanding of the relational encounter with an adolescent in long-term psychoanalytic psychotherapy, the therapist came to understand the extent of the adolescent's difficulties. Examination of the shifting transference-countertransference configurations made possible a deeper perspective on the patient's history, family dynamics, and life struggles and greatly influenced the development of the treatment. The convergence between the patient's tendency toward psychic deadness and the deadly seriousness with which the therapist had to confront the patient's seeking is presented as a focal aspect of the treatment.