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This paper uses a case illustration to explore how medical, psychiatric, and developmental diagnoses can affect identity development as youths move through adolescence into young adulthood. There are teens whose search for identity takes them through psychiatric territory as they deal with their changing bodies and longing for intimacy. Parents take their children for psychological, medical, and developmental evaluations to determine how to help them with issues such as peer relations, gender dysphoria, ADHD, signs of autism, learning disabilities, medical trouble, and other sources of anxiety. Their children acquire diagnoses, identifying with some and rejecting others. By adolescence, confused about not fitting in and not feeling normal, they want to know who they are and whether there are others like them. They cling to new identities and new people or groups with whom they can identify. The shift from passive suffering to active self-direction feels empowering. Accepting or rejecting diagnoses feels necessary for their mental health. Teens learn to use diagnoses to advocate for themselves, explain themselves, and argue with parents or friends who think they are making excuses for bad behavior. Embracing psychiatric self-definitions alienates some friends and attracts others, and they may shift their social groups accordingly. A case study brings these ideas to life.