Scientists define the gender frame of reference in a modern society (the concept gender means " a social sex") as a set of relations between men and women including informal and formal rules and norms of behavior, corresponding to the place, purposes and position of the two sexes in a society. In this article an attempt is made to analyze Chekhov’s stories from the point of view of gender problematics. From this point of view the classification of female images in Chekhov’s writing can be presented as follows: 1) "The new woman" who aspires to independence and incurs the duties of performing a traditionally man's role in society-Nataliya Gavlilovina ("Wife"), Lida ("House with an attic"), Nataliya Feodolovha ("Duel"), Nadya ("Bride"); 2) "the feminine" who sees happiness in the execution of a traditional female role-Olenka ("Dushechcka"), Anya ("Anjuta"), Pelageya ("The hunter"); 3) "the floozie" who externally keeps the features of the biological sex, but actually is deprived of aspirations to create a family and family happiness and uses men for the achievement of personal purposes-Anna ("Anna on a neck"), Ariadna ("Ariadna"), Olga ("A drama on a hunt"); 4) "the real woman"-Anna Selgeevna ("Lady with the dog"), Anna Aleksefna ("The Love").