In her current work on female adolescence, Carol Gilligan reported that girls lose their sense of relationship awareness and conviction as they enter adolescence. This article represents a psychoanalytic response to her findings. The response emerges from a need to expand the psychoanalytic perspective on adolescence in view of current developmental research findings as well as to address the fact that adolescence has been underemphasized in the psychoanalytic—including the feminist psychoanalytic—literature. Following a presentation of the extant psychoanalytic feminist perspective on adolescence, a comprehensive perspective is constructed from which to critique Gilligan's data. The foci of this perspective include (a) the importance of peer relationships and (b) the role of menstruation in marking a girl's entrance into womanhood, with particular reference to her change in self-experience and the quality of her maternal relationship. The article concludes with a discussion of implications for the psychotherapeutic relationship.