Utilizing three classic films, and psychoanalytic developmental theory, this paper explores the conscious and unconscious reasons why older women become sexually involved with teenage boys. After a presentation of aspects of young adult and midlife female development and a psychodynamic explanation for the developmental similarities between adolescence and menopause, each of the three films is summarized. The dynamics behind the women's behavior, as presented in the films, are discussed. The third section of the paper discusses similarities and differences among the three women and the negative effects on the boys' development.