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The author explores the notion of sexual difference, which Freud articulated in his vast work. The paper approaches different levels of theoretical and epistemological order, since the way of thinking about “difference” has crucial effects on clinical work. The point of departure was to analyse the changes that are observed in current subjectivities regarding the female condition and the changing itineraries of sexuality and gender, since the analysts’ explicit and private theories, as well as their beliefs and biases, are put into play in psychoanalytic listening. The paper focuses on the relationship of psychosexuality and gender with the concept of sexual difference and with “difference” as a category in itself. The objective was to explore the meanings of the concept of “difference”, in which sexual difference is certainly included as one of the expressions of “difference”. The author’s proposal is that there is not a single way of thinking about the notion of sexual difference in Freud’s works. This exploration enlightens the coexistence of dualistic and triadic ways of thinking in his oeuvre.