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Guilt in cross gender conditions is one of the most difficult manifestations of inner conflict to identify and measure accurately. While developing psychometric measurements of guilt in gender identity conditions in adults, the authors noted recurring themes in virtually all clients in their clinical practice over the past 25 years. To test their initial impressions of themes of guilt, the authors gathered data from both clinical experience and from research studies specifically designed to identify areas in which patients reported feelings of guilt. Data were gathered on a total of 787 patients, of which 685 were pre- and 102 post-operative. They found 13 themes of guilt in their subjects. The authors believe that understanding the primary sources of the special kind of guilt connected with gender dysphoria is crucial to understanding the gender dysphoric person. A major goal of their treatment is the elimination of the crippling effects of guilt. One of the authors offers examples from her clinical practice for this approach to psychotherapy. KEYWORDS. Gender dysphoria, gender identity disorder, guilt, psychometric measures, psychotherapy, sex reassignment, transgender, transsexual