The study intends to describe and compare the characterology and image of woman of the 19^th -century philosopher, Arthur Schopenhauer and Otto Weininger, a philosopher-psychologist living at the turn of the 19-20^th century. The philosophy of Schopenhauer and Weininger represents surprising coincidence concerning the role of woman in life, the differences between the two genders, and the inferiority of women. With some smaller digressions – such as the function of psychology, character and gender, the duality of gender roles, and the woman as a diametrical human being - we get hold of a picture of the two philosophers’ theory. The current study tends to introduce a kind of psychology which can be regarded as a psychological attempt preceding today’s psychology; furthermore, it examined the relationship system of individual and genders from an absolutely different perspective.