Psychotherapy with a highly intelligent African-American girl (Tiffany), a participant in a long-term, after-school program in a city in Connecticut, is presented from two periods in her life, first when she was ten and then when she was fourteen. Questions are raised about the value of the intervention, given the “whiteness” of her therapists and the degree to which she seemed, in general, to distrust white people. Some of the steps in the process of establishing trust are described, steps that included not only the testing of her therapists, but a powerful need to feel reaffirmed by those from her own background (“dark-skinned” men) who she believed, in the person of her father, had betrayed her when she was very young. The apparent usefulness of the therapy is finally described, keeping in mind both the complex nature of Tiffany's past and the ongoing struggle that she and her peers will have to undergo if they choose to leave home behind and enter the wider (persistently prejudiced) American world.