What does Winston's recollection about a prostitute reveal about him in "1984"?
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It reveals a jumbled mixture of things. It reveals how sexually frustrated he was/is, since there is nothing romantic or erotic in the meeting, but they have sex anyway. It reveals that he is taken in by the trappings of femininity: he mentions that it was the make-up that he found sexually exciting. It shows how vividly he remembers this, since he writes about all the details. Finally, it reveals that he's ready to rebel against the party
Winston's encounter with the prostitute is one of the events that foreshadows his eventual failure and destruction. It shows that Winston is driven by instinct and feeling as much as by reason, and that he can be tempted by his mere physical desires into taking actions that put him at risk for no real long-term advantage. It is a precursor of his sexual relationship with Julia, which although a much more attractive and healthier affair, was equally imprudent if Winston were really interested in resisting the rule of the Party effectively.
As his name indicates ("Winston Smith," from the hero Winston Churchill and the most ordinary of surnames, Smith), the protagonist of Nineteen Eighty-Four is presented as a very mixed bag of good and bad qualities. The prostitute incident is an early alert to the reader of one of his greatest flaws and a warning that he is doomed to fail because of his own inadequacy.
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