This paper draws on the theory and method of free association in psychoanalysis to frame an investigation of the content, structure, and function of the thinking expressed in conversations about sexuality and sexual health. The investigation emerges from an ongoing three-year study of the way adolescents, teachers, and peer sex educators negotiate and interpret the language of abstinence and the emotional terrain of sexuality in everyday speech and interaction. Through close readings of a film and related focus group data, the paper calls for attention to free associative movements of thought in sex education conversations. It argues that fostering free association in sex education will make room for the translation of sexuality into thought about the contours of sexuality in experience.