This article summarizes an adolescent psychotherapy case with a beginning doctoral level therapist in an urban community setting. The author reviews the course of treatment with particular attention to clinical issues related to developmental changes for both the patient and this beginning therapist. Vignettes are used to illustrate the patient's conflicts and to explore therapist “mistakes” that led to inevitable frustrations with, and eventual breakthroughs in, the work done by the pair. These include, but are not limited to, tracking authenticity as a mode of object-relatedness, complementary and concordant identifications that help to illuminate transference and countertransference themes, multidetermined impacts of voluntary versus involuntary immigration on identity development, therapist reveries as an aspect of the therapeutic communication worthy of contemplation and future exploration, and direct uses of reverie experiences in supervision as representative of the content co-created in the patient-therapist dyad.