This article explores what we can learn about truth and meaning from fiction, through a reading of George Orwell's (Eric Blair's) dystopic novel "Nineteen Eighty-Four" (1949) in the light of philosopher Stanley Cavell's notion of "lived skepticism." The article suggests that we can conceive of the novel as portraying "lived skepticism" of a "totalitarian variety." This lived skepticism is a condition of uncertainty and doubt forced upon the members of the novel's totalitarian society through indoctrination and physical and psychological torture. The article argues that the novel imagines three areas of totalitarian lived skepticism: lived skepticism with regard to the external world, with regard to language, and with regard to other minds. Among these three, the article centers on totalitarian lived meaning and other-minds skepticism. In particular, it asks who could be considered to be the main character's "best case" of knowing another mind. It furthermore asks what relationship between intimacy, privacy, love, cruelty, and knowledge the novel imagines to obtain within its fictional universe. The article argues that Orwell's novel gives us a nightmarish vision of the annihilation of the possibilities of love, by showing us The Party's perverted pedagogy of unlearning. Through the dystopic world of "Nineteen Eighty-Four," the reader is offered a potent object of comparison by which she can trace her own moral and sense-making boundaries: what does it mean at the end of the novel that the main character "loves" Big Brother? Can we understand imaginatively what it would be to love Big Brother? Or is the word "love" here merely carrying the illusion of sense--an illusion served to the reader as a pedagogical tool with which she may better learn how to tell sense from nonsense?