This paper aims to analyse the lessons about truth and relevance that may be gained from literature by reading George Orwell's dystopian novel, Nineteen Eighty-Four in the context of philosopher Stanley Cavell's idea of “living scepticism”. According to the idea, we can view the novel as a representation of life under a totalitarian system. The protagonists in the totalitarian society of the novel experience this experienced scepticism, which is a state of confusion and doubt brought on by indoctrination as well as physical and psychological punishment. The three main types of authoritarian experiences that are imagined in the book are scepticism of the outside world, scepticism of language, and scepticism of other people's brains. The focus of the article is on the scepticism of other minds and totalitarian lived meaning among these three. It explicitly inquires as to who may be the “perfect case” in order for the main character to appreciate the viewpoints of others. Intimacy, privacy, love, brutality, and knowledge are all related in some way in the novel's imagined world. The article contends that through exposing us to The Party's peculiar unlearning pedagogy, Orwell's writing offers us a nightmare image of the elimination of the possibilities for love. What does it mean at the book's conclusion for the main character to “love” Big Brother? In the dystopian society of Nineteen Eighty-Four, the reader might utilise these crucial questions to assess her own moral and intellectual limits. Can you imagine being so obsessed with Big Brother? Or does the use of the term "love" in this situation simply aim to provide the reader the ability to distinguish between speech that makes sense and speech that doesn't?