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What is the overall reason that Winston begins writing in the diary?
Winston is a rebel and wishes to go against the Party and their rules, thus writing in a journal that is deemed unacceptable.
Winston wants to be sure his memories are not fictitious but real.
Winston wants to have proof that both he and O'Brien had feelings of hatred and disgust for the Party.
Winston feels the need to pour out his thoughts in a stream of consciousness onto paper to solidify his beliefs that his thoughts are real.
Winston is an aspiring author and, though it's against the Party policies, he secretly works on his novel.