What is Winston's greatest pleasure in life in 1984?
Winston's greatest pleasure in life is his work. His job at the Ministry of Truth is to rewrite history, doctoring documents so that they correspond with Big Brother's version of the truth. Most of Winston's work is
"tedious routine, but included in it there (are) also jobs so difficult and intricate that you could lose yourself in them as in the depths of a mathematical problem - delicate pieces of forgery in which you had nothing to guide you except your knowledge of the principles of Ingsoc and your estimate of what the Party wanted you to say".
Winston likes his job because he is good at it, and he looks upon it as a challenge and a diversion in his drab life. He is so skilled at what he does that he has even on occasion been entrusted to rectify the Times leading articles. Winston no longer thinks of...
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what he does as forgery - the materials he works with have so little connection "to anything in the real world, that to him, it is "merely the substitution of one piece of nonsense for another" (Part I, Chapter 4).
What is Winston's favorite thing in life in 1984?
Winston's favorite objects are things from the past: his diary, the coral, and his memory of his mother.
If Julia is a rebel below the waist, then Winston is rebel above it . His first form of rebellion is writing in his journal. This thoughtcrime is the basis of all other crimes. In the end, he is seduced by empty words: the words of O'Brien and the book of Goldstein.
He is also fascinated with beautiful things, namely from the past. He can't figure out why anyone would have wanted a coral paperweight, something that is beautiful for its own sake. In 1984, things are supposed to only have functionality, to be utilitarian, soulless, unadorned. The coral too is used to seduce Winston into renting the flat upstairs, where he ultimately caught.
He often dreams of his mother. She sacrificed herself for him, and he has yet to feel safe without her. He has also yet to feel the same kind of love from a woman. Julia presents the possibility of love, but in the end, he aligns himself with O'Brien (the double-agent) instead of Julia.
So says and Enotes editor:
Separated from his parents at an early age, he is raised in an alien culture, destined to be its savior, should he choose the calling. His magic talisman could be said to be this diary, with which he will set the future free from tyranny. Akin to the Arthurian legend of the Fisher King, Winston’s varicose veins are an unhealable wound, one which begins to improve once he connects with Julia. The exercise of free will inherent in their affair is an attempt to break the power of the evil Party. However, Winston fails in his quest in that he submits to torture, betrays Julia, and grows to love Big Brother.
In the end, all that Winston loves is a facade, a trap, a fantasy. The only thing real in 1984, unfortunately, is pain.