Drawing on contemporary theory of female development that focuses on the dynamics of the mother/daughter relationship regarding issues of separation and individuation, this article examines the treatment of a middle aged mother as she navigates her way through her daughter's adolescence and early adulthood. Psychoanalytic object relations, psychoanalytic relational theory, and feminist theory serve to frame an understanding of the case material in terms of developmental challenges that are uniquely female. Issues around mother/daughter attachment, separation, competition, conflict, and love are explored in the relationships between the patient and her mother, the patient and her daughter, and the patient and the therapist. The therapist's countertransference, intensified by her relationships with her own mother and daughter, suggests the possibility of both pitfalls and opportunities in the treatment. The article attempts to address a gap in psychoanalytic developmental theory, which offers little understanding of the challenges for women in midlife.