In the context of thinking about factors that underlie therapeutic change in adolescent treatment, this paper discusses the significance and nature of self-disclosure, authenticity, and humor in the relationship between an adolescent therapist and an adolescent patient. A case study highlights how particular aspects of the therapeutic relationship aid our adolescent patients in strengthening their observing egos, attenuating their preoccupations with concrete and/or binary thinking, and facilitating their ego-ideal maturation. The capacity to laugh at oneself is discussed in some detail, as is the importance of the nonhierarchical nature of the therapeutic relationship.