This chapter reviews the category of sexual difference in S. Freud’s works far-reaching problems and questions concerning both theoretical perspective and clinical practice. It describes the relation as extremely complex; it involves, among other issues, theories of sexual difference. The chapter shows that it was the German Romantics from whom Freud drew inspiration that described the aspect of the human condition. It discusses several levels in relation to the subject: ideological, descriptive, and epochal aspects; epistemic and logical foundations; hypotheses in Freud’s works that are original discoveries surpassing these determinations. The chapter explains Freudian discourse on sexual difference and masculine-feminine polarity in order to identify obstacles and blind spots in the theory and their effects on clinical practice. It is vital to detect propositions directly or indirectly related to ideological, epochal discourses concerning women to consider which explanations respond to accepted epistemic logics and which surpass conditions to form theoretical developments that transcend ideological or epistemic conditioning.