This article describes the working method of our study group comprised of former Chestnut Lodge Hospital therapists and focusing on understanding therapeutic work with severely disturbed adolescents. Using process material from one therapy session, the therapist’s commentary on her feelings and reactions in the session, and the group’s discussion of the work, we explore factors disrupting the therapist’s moment-to-moment capacity to maintain a theory of her own and the patient’s minds. We then discuss what allows her to refind her theory of mind in the face of the patient’s aggressive nihilism and her own sense of loss. Salutary factors included the therapist’s empathy for the patient’s shared sense of grief, the patient’s offering the therapist cues to his inner state, and the dyad’s capacity to tolerate the therapist’s vulnerability in the patient’s presence.