Throughout history, there have been numerous persistent discriminatory practices against women - stereotypes, lack of freedom, denial of equal opportunities, exclusion from political life and lack of access to education. The situation was no different in the US, where the same prerogative prevailed for centuries, characterized by pervasive gender inequality and entrenched patriarchal norms. It was not until the second half of the 19th century that a change began to take place, starting with the rise of organized women’s rights movements and events. It is undeniable that these laid the foundations for the further development of women’s rights in the 20th century. The question, however, is whether they were enough to eradicate the stigma that was so deeply ingrained in society, not only in America, but throughout the world. By analyzing two novels, Kate Chopin’s “The Awakening” from 1899 and Sylvia Plath’s “The Bell Jar” from 1963, we not only gain a deeper insight into the conditions that a woman had to accept in order to be considered worthy, but also into the effects of these conditions on women themselves. What happens when one cannot find peace and happiness within the constraints? Who is to blame: society, which sets the ideal, or the outsider who cannot function within the group? By comparing the narratives, characters, and themes, this study will explore women’s conflicts between their desire for autonomy and society’s expectations while seeking to broaden our understanding of these classical works and their applicability to contemporary conversations about feminism and mental health.