This article examines how modes of play in psychoanalytic child treatment can create clinical momentum and resumption of psychological growth through a process of procedural enactment, empathic immersion, and ongoing repair of fragile relational bonds. The author portrays a process of treatment that allowed an engagement of previously dissociated affect states and served to build expanded capacities for both self-reflective thought and creative action. The author provides clinical material that portrays work with a schoolyard “bully” in a series of enactments that enabled her to empathically engage with the patient while also helping the patient to establish new empathic capacities—for both self and others. Together, the patient and the analyst constructed a cardboard toy boat, which came to serve both as a vivid depiction of the vicissitudes of the emergent analytic third, as well as a symbol of the forward edge of development.