Why is Winston so reckless in 1984?

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One could argue that Winston Smith's recklessness is a result of his desperation to experience humanity as originally intended. In Oceania, Winston lives an oppressed, dangerous life, where he is at the mercy of an omnipotent, hostile government, which controls every aspect of society. Winston is under constant surveillance and knows that the Thought Police is watching his every move. Despite the overwhelming pressure from the agents of Big Brother and his orthodox peers, Winston cannot help himself from committing thoughtcrime. The second Winston expresses his hatred towards the Party by writing "DOWN WITH BIG BROTHER" in his diary, he knows that he is doomed. Winston understands that it is only a matter of time before he is arrested, tortured, and killed by the Party, which motivates him to make reckless decisions. These reckless decisions allow Winston to experience life as originally intended and give him the rare opportunity to embrace his humanity. Winston experiences love, freedom, and leisure for the first time once he comes to terms with his fate. Winston's desperation to embrace his humanity and enjoy life motivate him to make reckless decisions before he is eventually brainwashed by the Party. One could argue that the brief moments of freedom and joy that Winston experiences were worth the tragic consequences.

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In this book, Winston Smith is reckless and takes actions that make it almost inevitable that he will be caught.  The reason for this is that he is desperate to the point where he does not really care that much if he lives or dies.

Winston wants to be a real individual.  He wants to be able to have the kinds of personal relationships that are not possible under the Party.  He wants to be able to have real memories and real knowledge.  Again, this goes against what the Party wants.  Because he wants these things so much, and because they are impossible to have in his society, Winston is desperate.  He hates living the life he has and so he doesn't think it would be that much of a loss if he dies.  This makes him reckless.

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