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What do you think O'Brien has to share with Winston?

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Why is O'Brien showing so much interest in Winston and his writing?

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Why do you think O'Brien was so focused on Winston's article and so worried about Winston?

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Do you think Winston's mom is a symbol of the past and why?

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Why do you think Winston believes he's responsible for his mother's death?

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Did O'Brien bring up syme on purpose to hint he knows what actually happened

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What do you think happened to Winston's mom after he ran away?

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Is the Brotherhood that Julia and Winston joined real or is it just a trap created by O'Brien?

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Do you think O'Brien is really recruiting him or is it a trap?

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What do you think about Winston's distinction between confession and betrayal when talking to Julia?

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Was Syme connected to O'Brien somehow?

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Why do you think O'Brien is part of the Brotherhood if he has all these luxuries that it describes in the Chapter?

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How do you think O'Brien and Winston's conversation foreshadow O'Brien possible connection to the thought police?

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Why does his memory just repress after so long of not having it

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Do you think Winston's family will reappear later on in the book?

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Why is O'Brien able to turn off his telescreen?

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What do you think Julia murmured to O'Brien as she faced him?

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How did O'Brien realize that Winston is unorthodox?

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Do you think that O'Brien will be punished because of his actions in regards to his mentioning of Syme, and the writing down of his address?

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What do you think was the reason that Winston's mother was taken

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Why would O'Brien so plainly commit thought crime in public?

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What was the terrible thing that the mother was waiting for?

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Why do you think O'Brien gave the address in front of the telescreen?

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Why is Winston so afraid of O'Brien?

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If Winston's mother didn't care for him and his sister would he still be a free-thinker?

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Why was O'brien so quick to trust Winston and Julia

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What do you think Winston meant by "[c]onfession is not betrayal"?

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Considering Julia's desire to be sexually rebellious for thrill, do you believe there promise means anything?

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Is O'Brien trustworthy or setting them up?

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Do you think that Winston would have said yes to leaving Julia if she didn't answer O'Brien first? Why or why not?

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In what way will the servant for O'Brien will end up being significant to Winston and Julia?

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Do you think that O'Brien giving Winston the book will lead him to start a revolution?

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What possible deeper meaning could there be to O’Brien giving Winston the dictionary?