“Conflicted” succinctly describes Ernest Hemingway. He had a strong desire to make his parents proud of him but this was in constant conflict with his need to tell a story, warts and all. Of particular importance is his relationship with his mother and the crippling effect it has on his relationships with women. Hemingway’s life becomes a series of dysfunctional relationships that fail to meet his needs, leaving him perpetually searching for the right woman. Kert posits that Hemingway’s contempt for women is related to his inability to make the transition from lover to husband, fueled by Hemingway’s belief that his father surrendered his manhood to Grace Hemingway. Ernest, haunted by his parents’ relationship continues to associate negative connotations with the term “husband,” leaving Hemingway in constant fear of becoming his father, poisoning his marriages, and coloring the relationships Hemingway depicts in his short stories. Evident across the arc of Hemingway’s short stories is an evolution in his skill as a writer, but also in the development of his female characters. Over his career, Hemingway develops a female voice that rings true, and he skillfully uses it to portray female characters who are evolving into strong self-reliant women. In these stories, there is a gradual shift in the dynamics of the relationships as Hemingway’s fictional women struggle to climb from under their man’s domination. Yet, these strong self-reliant women are not fully accepted by Hemingway’s male characters, leaving a palpable tension between Hemingway’s fictional men and women. This tension can be attributed to Hemingway’s ongoing love/hate relationship between himself and the self-reliant women in his life. Hemingway never recovers from the emotional damage inflicted by his mother, evident in his personal life and in the dysfunctional relationships in his short stories. He remains vigilant and is concerned that he will end up like his father and be controlled by a domineering bitch. However, Hemingway exerts so much control in his relationships and becomes a version of his mother as he dominates his significant others. In his life, he transitions from an angry resentful child-man to a young husband, a reluctant parent, a ladies’ man, and an adventurer. Likewise, his perception and portrayal of women in his short stories keeps pace with his personal experiences. These female characters sometimes reflect the women in his life and sometimes reflect Hemingway’s insecurities as a man, and often a seamless melding of both.