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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
In George Orwell's 1984, Mr. Charrington’s upstairs room provides a welcome but brief respite for the characters of Julia and Winston. The dystopian futuristic society of Oceana is extremely stressful for people like Julia and Winston, and this opportunity to get away from its constraints and the prying eye of Big Brother gives them a chance to be themselves. This also gives the reader a chance to see what these characters are like under slightly more normal circumstances.
However, Winston and Julia also realize that they are going to get caught at some point; they harbor no illusions about their ability to overcome the power of the Party. When they are finally caught, Winston knows that he will be tortured and asked to turn on Julia, which he tries not to do. However, the Party’s torture methods are too effective, and he eventually does.
The end result of all of this is that Winston realizes that he cannot win and finally gives in to the Party’s demands. This leaves the reader with a feeling of doom and foreboding—the individual is no match for a government that has unchecked power and unlimited resources.
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