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This article draws on a study of tomboys to reflect on developmental theory in psychoanalysis. To illuminate the power of chaos theory and nonlinear dynamic systems theory in understanding gender and sexuality, I trace three lines of theoretical work on gender, relevant to conceptualizing tomboy love and tomboy identity. First, I reexamine the work on gender development in which bodily life as the wellspring and organizer of gender is prominent. The second strand begins with the organization of gender development proposed by Stoller (1976) and taken up and developed by Fast (1984). Its most articulated form is in the work of Benjamin (1988, 1993). This line of argument conceptualizes gender development through the pattern of relationships and the resultant identifications. The third strand concerns the understanding of “masculinity” in women and the evolution of work on bisexuality.