In George Orwell's 1984, what does Winston dream about his mother, O'Brien and the girl with dark hair?

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In 1984, Winston has numerous dreams which are significant in developing the central themes of the text. 

In Part One, Chapter Three, for example, Winston dreams about a girl with dark hair. In the dream, she is running towards him in a field when, all of a sudden, she tears "off her clothes" and flings "them disdainfully aside." 

During this same sequence, Winston also dreams about his mother, specifically that they are in the "saloon of a sinking ship," about to be sucked down to their deaths. Winston dreams of his mother again in Part Two, Chapter Seven, in which she makes a gesture with her arm that is repeated by a Jewish woman thirty years later. It is also in this chapter that Winston reveals another dream of his mother in which he steals some chocolate from his sister. Winston shamefully runs away and when he returns, his mother is gone. This dream is, in fact, a repressed memory from Winston's childhood.

Winston also has a dream that features the voice of O'Brien. The reader learns about this in Part One, Chapter Two when Winston recalls this dream in which he is walking through a "pitch-dark room" when O'Brien's voice says to him: "We shall meet in the place where there is no darkness."

What is important about these dreams is that they represent Winston's inner sense of rebellion. The dreams of his mother, for example, are symbolic of his desire to overthrow Big Brother and return to a society in which freedom of thought and self-expression are encouraged. Similarly, the dark girl's removal of her clothes represents not only Winston's sexual repression but also his hopes of shedding the Party's control and being liberated. These dreams plague Winston, particularly in the first part of the book, and contribute to the plot's development by urging him to act against the Party. 

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