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This paper details the diagnostic discourse that has accumulated around feminine boys, including the traditional presuppositions of Gender Identity Disorder (GID). The GID discourse is examined for the ways in which it is built upon unquestioned beliefs about masculinity. Distinct from most modern considerations of gender, no effort has been made to critically theorize gender when thinking about feminine boys; masculinity is as masculinity was. Consequently, we are left with modes of diagnosis and treatment that are out of synch with modern social life, and a set of ideas that do not proceed from an adequate understanding of the range that is masculinity. New sustaining ideals are in play, and in accord with these ideals an argument is made for a new mode of psychotherapeutic address. The traditional individual trauma explanation for GID is questioned. Particular emphasis is given to the ways in which this traditional GID discourse fails to reckon with how masculinity is held in place by the strong arm of regulatory anxiety. A new position that incorporates a greater appreciation for the role of social trauma and melancholia is offered. It is argued that a theory that offers insight into the workings of melancholia as it builds the feminine boy affords a more robust set of ideas through which to contemplate the boy. In turn, we come upon a better avenue of psychotherapeutic action—one that does not employ behavioral strategies that reinforce social exclusion.