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Girls lose their voice at adolescence, as feminist scholars and researchers Gilligan, Tolman, and Brown have demonstrated, and must gain the ability to resist cultural norms in order to stay connected to and further develop an authentic sense of self. In this paper I apply feminist views to the relational psychodynamic treatment of a teenage girl and explore the ways in which dissociated transgenerational dynamics contributed to her loss of voice at adolescence. Throughout the paper I cite examples from literature and popular culture that suggest the widespread reach and emotional challenge negotiating generational and gender differences can have at this time. I describe the therapeutic approach I employed to “catch” or rework the dynamics in the attachment system through a combination of individual and family sessions. The clinical work raised questions about the gender bias in psychoanalytic theory's discussion of the second separation-individuation at adolescence. My paper concludes with recognizing the importance of working within the intergenerational relational context in which adolescent girls' struggles are embedded.