This article carries out comparative literary research of the short story "The Lady with the Dog" by the Russian writer Anton Chekhov and the novel “The Great Gatsby” by the American writer F. Scott Fitzgerald for determining the possible mutual influence between these two authors and their works. For achieving the set goal, the article reveals the most significant similar incidents and differences in relation to the aspects of love, ego, and trauma that were selected for the analysis. The comparison relies on the Freudian view of love and trauma in order to analyze the psychological struggle after the loss of love experienced by the protagonists of the aforementioned literary works – Gurov and Gatsby. The scientific novelty consists in comprehensive comparison of the theme of love between the authors and their protagonists, as well as with the protagonists themselves. Unlike other existing scientific works, this publication compares the psychological aspects of not only love, but the trauma and ego of Gurov and Gatsby as well, revealing the similarities and differences between the aspects of love, ego and trauma alongside their perception by the protagonists. Both main characters fall in love with the women who are married to other men. Thus, they both have experienced a traumatic situation they could not cope with. The research sheds light on the similarities between Chekhov and Gatsby and their narrators in both case studies. The acquired results can be applied in practice of literary psychoanalytic criticism, as well as in practice of comparative research.