Hemingway’s and Cheever’s short stories represent a fertile ground for an extensive analysis of their stance on marriage and love. Their narratives create a bridge, connecting time periods between and after the two most destructible world wars. Both writers are influenced by their personal experiences connected to their childhood upbringing, the crumbling marriages their parents had, and the war atrocities. Hence, Hemingway and Cheever shift their narrative focus to rejection of love as an emotion with a positive outcome by showcasing corrupted marriages, separations and divorces, and creating characters to mirror their lives and experiences. In addition, Hemingway and Cheever show that there is a connection through their vision of love and marriage which reflects the post-World War I and World War II American state of society. Both authors detect some critical issues tearing lovers and marriages apart. Hemingway’s main focus is on wealthy and emotionless men who despise the idea of marriage and reject women who threaten their masculinity, while exploring deeper issues connected to selfishness, solitude, intimacy, parenthood, power, and emotional weakness in men. Cheever’s narrative revolves around the upper-middle class and their marital problems, tackling similar issues as Hemingway – weakness, betrayal, solitude, parenthood, and delusion. Both authors even touch upon the suicide in connection to emotions and marriage. Therefore, the aim of this thesis is to analyze how Hemingway and Cheever portrayed love and marriage in their short stories and to clarify which issues concerning love and marriage emerge from the background of characters’ life situations, based on social conditions of the time, and the writers’ personal experiences.