In the attempt to analyze any type of literary work, one cannot focus on one single aspect if he/she wants to present the complex web of notions and ideas which make a work of art deserve its name. A story is not simply a chain of events ordered in one fashion or another. Every story consists of numerous strings which intermingle, attach themselves to one another and even disrupt each other. The main goal of this paper is to try to concisely present this complex web of strings in the works The Awakening by Kate Chopin, “The Yellow Wallpaper” by Charlotte Perkins Gilman and Fear of Flying by Erica Jong - more precisely, the influence that society, the gender of the main characters, and the psychological issues have on the heroines and the way they behave because of these influences. The complexity of this task deems it necessary to analyze why the character acts or thinks a certain way and this means a lot of different influences need to be taken into account: from the relationships in their families, to their own relationships to the people surrounding them – husbands, lovers, doctors, friends – and further to the inner thoughts and doubts of the heroines. This paper attempts to follow the path the three young women take in order to find out who they are, what role they play in the societies they live in and how they can live up to their full potential.