what is winstons feelings towards the purchase of the diary show?
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Winston knows owning a diary could get him killed or at least five years in a work camp. Still, Winston is going crazy inside. He needs to express himself. Winston needs an outlet for all his aggression that he has against the Party and what it stands for. Winston needs this outlet, no matter how small or symbolic, to write down that he exists as a separate entity from the Party.
Winston begins his diary with a description of going to the Flickers or movies,
"April 4th, 1984. Last night to the flicks. All war films. One very good one of a ship full of refugees being bombed somewhere in the Mediterranean. Audience much amused by shots of a great huge fat man trying to swim away with a helicopter after him, first you saw him wallowing along in the water like a porpoise, then you saw him through the helicopters gunsights, then he was full of holes and the sea round him turned pink and he sank as suddenly as though the holes had let in the water, audience shouting with laughter when he sank."
Winston is bemused by what he sees. To us it is horrific but to Winston, he is confused. Why are these people cheering? Why isn't he cheering? Winston is trying to gauge meaning.