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Winston records in his diary his memory of his last sexual encounter, which was with a prole prostitute.Winston does not really know what it is to enjoy a sexual encounter. His last wife, Katherine, loathed sex and only acted on it as a duty to the party. Winston writes about the Prole woman's painted face (make up) He likes this only because make up is prohibited by the Party. He discovers that the Prole woman is much older than he thought. He goes through with it anyway. The experience was entirely disagreeable but then Winston feels very little about anything. At least feeling revulsion and guilt is feeling something in his rather dead soul.