1984 Questions and Answers
by George Orwell

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What does Winston's recollection about a prostitute reveal about him in 1984?

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The sequence of the book that the question is asking about is in chapter 6.  In terms of plot, Winston's memories of the event serve as a way to foreshadow his eventual affair with Julia as a way to rebel against the Party.  In terms of character development, this chapter serves as a way to show readers Winston's ever growing dissatisfaction with the Party.  The chapter shows that his anti-Party feelings are growing.  The feelings that caused him to write "Down with Big Brother" in his journal were not a mistake or a one-time event.  

Winston's recollection of his time with the prostitute causes him to mentally admit to his readers that what he wants most is to actively defy the Party.  He sees sex as a possible way to do this.  During his reminiscing, Winston tells readers that the Party made it a priority to remove all passion, joy, and pleasure out of the sexual act; therefore, having passionate sex with a Party member was a legitimate way to rebel against the Party. 

Its real,...

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