This article presents the psychotherapy of a latency-age boy that challenges both the patient and his psychotherapist. While the boy seems to develop well after a short time of treatment, the psychotherapist remains concerned about his continued submissive style. She explores ways to convey to the boy her understanding of his inner world but feels with each effort that the treatment is at the edge of failure. The critical clinical moment occurs in the session that the boy had secretly planned to be his last. This crucial juncture creates the opportunity for this dyad to develop a common language. In the pleasureful playing that unfolds, they use verbal and nonverbal exchange to build a new foundation for their relationship.