George Orwell's Nineteen Eighty-Four is one of the most influential books of the 20th century, yet despite being widely studied linguistically and politically, the relationships between the characters have largely been ignored. In the present article we investigate the object relations of the protagonist, Winston Smith, using the narrative approach of the qualitative method in the book's prose, and proceed to analyze the dialogues and accounts of Winston's experiences as given by the omniscient narrator, through the investigative technique of applied psychoanalysis. Locating the relational dynamics in the dystopian context of Nineteen Eighty-Four, and following the Kleinian thinking as a guideline, this article stresses the impact that the reopening of the oedipal narrative has on the protagonist's aggression and loneliness, leading him to develop a love relationship with Julia that contains and transforms his past traumas, and to identify, with destructive consequences, with the idealized father figure of O'Brien. Throughout this article, the sublimative and reparative role of Winston's quest for the past is highlighted, showcasing his attempt to mourn the death of his mother for which he holds himself responsible, and his sociopolitical drives and anguishes are shown to conceal the desire of being loved, forgiven and understood.