A 30-month-long training program in child and adolescent psychotherapy was established in response to specific Israeli and Palestinian mental health services’ needs. Trainees came from Israel, the West Bank, and Gaza. This article addresses the rationale for the program, the opposition it encountered upon its inception, and the empathic processes that arose in the training group through a short vignette from a group supervision hour. It demonstrates the delicate nature of empathy, and its retreat in the face of conflict and aggression. Attention to empathic processes is presented as central both to psychotherapeutic relationships, as well as to the process of learning from group dynamics. The group’s growing capacity for empathy paralleled an increased appreciation for complexity and meeting the unknown personal territory of another. Relating to the Israeli-Palestinian context of the group, enabled an expanded ability to recognize one another’s humanity, while accepting existing political conflicts and experiential differences.