This thesis deals with a less frequently analysed aspect of George Orwell's dystopia titled 1984 (1949): the dynamics of the two major relationships of the main character, Winston Smith. The basic premise is that an analysis based on the symmetry and asymmetry of his relationships with O’Brien and Julia can provide a new perspective on some of the fundamental issues of the novel, such as its spiritual and religious dimension and its portrayal of the dichotomy of the body and the mind. Based on four theoretical discourses—that of torture, Foucauldian confession, Bataillean eroticism and eschatology—I explore the way Winston and O’Brien’s “strange intimacy” takes precedence at the plot level over the more conventional, unambiguously romantic affair between Winston and Julia. At the centre of the analysis are the Ministry of Love torture scenes, in which the potentially homoerotic Winston–O’Brien relationship is elevated to a spiritual level and an alternative, sacral temporality, intercepting the more traditional, physicality- and historical time-based relationship Winston has with Julia.