How does Mr. Charrington's upstairs room affect Winston and why?
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Ah, an interesting question. At first it gives him a great freedom. He has a place relatively free of his oppressive society, and one with glimpses of the past world. It gives him a place to have sex with Julia (and to read). It lets him feel free.
At the same time, though, he's really just getting himself deeper into trouble. He's engaging in thought crime, and he's been under surveillance the whole time. Eventually, he's arrested, and a good portion of the reason why is the time he spent there.
in addition WInston feels drawn to the past. Mr Charrington's store reminds him of it, he bought the paperweight and diary in that store. He feels relatively safe and he thinks the party doesn't know what he is doing in there
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