The diary is a symbol for Winston's desire to be free. He is unable to speak his mind, think his true thoughts, or do anything that may mark him as a suspicious character. Even his facial expressions can give him away...he must be in complete control of himself all the time. In the diary, he can write what he is thinking and feeling without the fear of being turned in by someone nearby. Of course, there is always the possibility that the diary will be discovered, but as long as he writes in it where the telescreen can not see him and he keeps it hidden, he can be relatively certain that his thoughts are safe.
It is not until his actions with Julia in the hidden apartment are discovered that the Thought Police search his home and also discover the diary which helps to incriminate Winston.
The diary is a symbol of the freedom he desires. It represents a time when all people, like the Proles, were able to think and express those thoughts freely.
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