The adolescent must deal with the transformation of puberty, disengage from childhood objects, and establish a sense of separate and distinct identity. Shame is an affect that has been largely ignored and misunderstood within the psychoanalytic literature. Psychoanalytic scholars have emphasized the affect of guilt, which represents internal conflict between the ego and superego. Subsequent psychoanalytic scholars modified Sigmund Freud’s views and stated that shame results from a conflict between the ego and the ego ideal. The chapter demonstrates the case of “Jane”. Jane was quite efficacious in keeping her mother’s attention focused on her worries and phobias, causing intense jealousies and antagonistic feelings to surface among her siblings and father. Jane settled right into her analysis, attending her sessions with a sense of relief as she told me her stories and troubles with girlfriends and sisters and parents. She had a difficult time in her summer camp with many social problems, always feeling left out and isolated.