In the course of my thesis, I attempted to form an idea of the "lost generation" as represented in the novels "The Sun Also Rises" (1926) by E. Hemingway and "The Great Gatsby" (1925) by F. S. Fitzgerald. The research was based on the three major questions. First of all, I examined how the image, social position, and psyche of the ‘New Woman’ in the 1920s is represented in the female characters in the selected texts. Then, I analyzed how the new notion of masculinity is embodied in the protagonists and their relationships with the beloved women in the stories. Further, taking into consideration the answers to the first two questions regarding gender roles, I discovered the correlation between the traumatic experience of representatives of the era and their failure to achieve happiness in the post-war reality. The focus of my thesis is interdisciplinary, being situated at the intersection of history, literary analysis, and psychology in order to achieve a complete understanding of how the “lost generation” is depicted in the modernist novels of E. Hemingway and F. S. Fiztgerald.