Winston has many dreams in the novel which reflect his deepest fears and longings.
He first recalls a dream from seven years past in which someone says to him, "We shall meet in the place where there is no darkness."
In a second dream, he sees his mother and sister sinking away from him. He says of this dream that it became
a continuation of one’s [his] intellectual life ... in which one becomes aware of facts and ideas which still seem new and valuable after one is awake.
Both of these dreams show his deep longing for connection. He realizes, too, through dreaming, that his mother was one of the last people from the old days who could have a strong, loving relationship with her children such that Winston would feel his heart was torn out when he lost her. Winston is characterized as having loved his mother very much and now grieving for her and his selfishness toward her.
His third dream is a recurring one of the Golden Country, a pastoral place. In the current version of the dream, a beautiful dark haired woman takes her clothes off in a gesture of defiance against the Party. The dream characterizes his deep longing for connection and his desire to find a way to escape the world of the Party.
A fourth dream, also recurrent, is a nightmare where he is deceiving himself in not knowing what is behind a wall.
In a fifth dream, dreamt as he sleeps beside Julia in the room above Mr. Carrington's shop, his mother and his present life merge, all safely under the glass of the paperweight he bought, an object which represents his desire for escape. He thinks of the dream as
a vast, luminous dream in which his whole life seemed to stretch out before him like a landscape on a summer evening after rain.
This dream gives him comfort that he didn't kill his mother but also brings back very mixed memories of his childhood. It characterizes him as rehumanizing as his love for Julia grows.
In a dream in prison, he awakes when he finds himself crying out aloud for Julia: "Julia! Julia! Julia, my love! Julia!" It shows his desire to protect her.
He learns the following:
For the first time he perceived that if you want to keep a secret you must also hide it from yourself. You must know all the while that it is there, but until it is needed you must never let it emerge into your consciousness in any shape that could be given a name. From now onwards he must not only think right; he must feel right, dream right.
Winston's many dreams in the novel characterize him as a person longing for connection and love, haunted by the past, and capable of deep human feeling. They show that the actions he takes which may seem foolhardy—and are—such as trusting O'Brien or having an affair with Julia, come from a deep place of yearning and humanity within him. Dreams in the novel also foreshadow what is to come.