This article presents a commentary on the analytic treatment of a depressed, highly agitated, and often rageful adolescent boy in residential care. Given the boy's ongoing experiences of desperation, an interactive analytic treatment perspective seems to have helped to foster his psychological growth and sense of optimism about the future. It was an approach that at varying times focused on the discussion, symbolization, and enactment of massive, often overwhelming feelings of loss, misunderstanding, disappointment, and rage. From this persistent struggle in the face of despair emerged a growing sense of hopefulness, wishes for intimate human connection, and special feelings of attachment within the context of the here-and-now therapist-patient interactions. Over time, this adolescent boy became increasingly able to build a life founded on “new experiences” of the world, a life that was in striking contrast to his traumatic, disappointing past.