It is vital to examine a child’s temperament, attachment style, and goodness of fit between parent and child when evaluating symptomatic children. The case of an 8-year-old, pop-star-obsessed female, with low self-esteem, is the basis for this Clinical Case Conference. Participants learn to identify parent-child relational disorders and to recognize when a lack of goodness of fit might be contributing to psychiatric symptoms; to treat parent-child relational disorders by adapting to the child’s world; and to be flexible in treatment options for optimum effectiveness.