What is the difficulty/ dilemma that Winston faces in the book, 1984?

In 1984, we can sum up Winston's dilemma in the following way: he has become conscious of the party's control over himself and other citizens of Oceania and he wants to overcome it. This dilemma is a driving force in 1984 and we see numerous examples of how it plays out.

In Part one, Chapter One, for instance, Winston buys a diary but instead of writing in it, he spends a long time "gazing...

In 1984, we can sum up Winston's dilemma in the following way: he has become conscious of the party's control over himself and other citizens of Oceania and he wants to overcome it. This dilemma is a driving force in 1984 and we see numerous examples of how it plays out.

In Part one, Chapter One, for instance, Winston buys a diary but instead of writing in it, he spends a long time "gazing stupidly" at the paper. He is terrified of the telescreens in his apartment and of being found out by the party. When he finally plucks up the courage to write, he scribbles frantically all over the paper, as a sort-of cathartic release of his pent-up desire to be free. Over the course of Part One, Winston writes in his diary more frequently, as a symbol of his growing confidence in overcoming the party's control over his thoughts and actions.

In Part Two, it appears that Winston has finally found a solution to his dilemma. Firstly, he begins a relationship with Julia who encourages him to express his rebellious desires in a physical and sexual way. In addition, through conversations with Julia, he articulates memories about his early life, which he had previously repressed. Secondly, in Chapter Eight, Winston and Julia go to O'Brien's apartment where they openly discuss the underground resistance against Big Brother. It seems, then, that Winston has finally found a legitimate way of venting his inward rebellion and that, by becoming a member of the resistance, he will no longer have to demonstrate outward conformity.

But this is not to last. At the end of Part Two, Winston and Julia are arrested by the Thought Police. Imprisoned at the Ministry of Love, Winston expresses his lingering hopes of resistance to O'Brien, a member of the Thought Police. His dilemma has finally been solved but not in the way we expect. Through torture and Room 101, Winston is re-educated and reintegrated into society. He no longer harbours those same feelings of rebellion and independent thought because he now loves Big Brother and has no desire to overthrow him.