How does Winston's complexity change through book 1?

I think we certainly learn the depths of Winston's misery and complexity. We see Winston break the law and buy a diary. Winston simply cannot handle his pent up thoughts and emotions. He needs a release and his "secret diary" is all he has. We see that Winston has taken more and more chances. Through Winston's painful memory of his experience with an aged prole prostitute, we begin to understand the depths of the Party's sexual repression. The memory pains Winston. Because he was so desperate for a close sexual experience, he continued the encounter even after realizing that the heavily made up woman was toothless and old. I think Winston feels dead inside and is trying to feel something regarless of how painful or revolting it is.