This article distributes a psychological reading of William Somerset Maugham’s of Human Bondage according to Donald Winnicott, one of the eminent figures in object relations theory. Maugham’s works depict the life of people who are struggling with their destructive relationship. This might refer to their childhood lack of holding environment or it may be caused by shaping false self as the loss of play. Although, Maugham leads his novels’ characters toward success, they are entrapped in their incomplete childhood prototypes and consequently they choose inappropriate partners. Philip Carey is the protagonist of the novel who is orphan and he is sensitive because he has lost his parents and he is born with a club foot. These made him sad and alienated from others and led him toward proving himself as a successful person; while actually he is not. Incomplete childhood prototypes and lack of confidence result in wrong decisions and inappropriate accompanying. Object relations theory helps finding the hidden reasons behind the protagonist’s actions, feeling and what he chooses in his life.