Winston and John reminisce about an old man who used to be there, Peter. They sing the song Peter started singing on the way to the prison, one of the Defiance Campaign songs. John talks about how he had to urinate on the way to the prison, but wasn't able to, so had to hold it in the whole way. They reminisce about the whole journey to the prison, how it was their first time on a boat. "Remember your words when we jumped off onto the jetty?" John says, remembering that Winston said "Farewell Africa!" as they arrived at the prison.
A stage direction tells us that John suddenly realizes what his release means to Winston, who has been sentenced to life in prison. He tries to cover his tracks, saying, "Look, in this cell we're going to forget those three months. The whole bloody thing is most probably a trick anyway. So let's just forget about it."
Scene 3. Later that same night, John cannot sleep, and gets up to get some water. He begins to count the days of three months, when Winston wakes up and catches him. John tells him it's only 92 days left and tries to go back to sleep. Winston says, "They won't keep you here for the full 3 months. Only 2 months. Then down to the jetty, into a ferry-boat...you'll say goodbye to this place...and straight to Victor Verster Prison on the mainland. Life will change for you there. It will be much easier. Because you won't take Hodoshe with you. He'll stay here with me, on the Island." He goes on to say that he will work at the vineyards, and his diet will change, and eventually he will be released.
John tries to remember what he was wearing on the day they locked him up: a white shirt, black tie, grey flannel pants. He cannot remember the socks. Winston keeps narrating the path to freedom, and when he gets to the part where John is released in New Brighton, "John breaks the mood as the anticipation of the moment of freedom becomes too much for him." He tells Winston to stop narrating it, but Winston keeps going, talking about the reunion with his family. "You'll tell them about this place, John, about Hodoshe, about the quarry, and about your good friend Winston who you left behind," Winston says.
Winston imagines John going out with "the boys" and them finding him a woman. He describes the sexual experience John will have when he gets out and John gets more and more upset, yelling, "Why are you punishing me?" Winston tells John that his freedom "stinks" and it's driving him insane.
Winston says he ended up next to old Harry at the quarry that day. Old Harry is also serving a life sentence, and Winston describes him thus: "He's forgotten himself. He's forgotten everything...why he's here, where he comes from." Winston says he also forgets why he is there, and John tells him he is there for his political ideals.
John sinks to the floor, and a stage direction reads, "Winston almost seems to bend under the weight of the life stretching ahead of him on the Island...When he speaks again, it is the voice of a man who has come to terms with his fate, massively compassionate." Winston apologizes to John for the fact that he is inevitably going to forget John.
What begins as an innocent reminiscence about their journey to the prison becomes darker as they keep remembering. John remembers how they became close almost immediately, as they were shackled to one another. They laugh about the harrowing journey to the island, how the prisoners were all packed into the back of a truck. Then, when John remembers Winston's parting words to their continent of origin, "Farewell Africa!" he realizes that his early release is a victory for him, but a slap in the face for Winston.
When John reminds him what he said upon arrival at the prison—"Farewell Africa!"—Winston becomes almost catatonic. The stage direction reads, "The Mood of innocent celebration has passed. John realizes what his good news means to the other man." Winston, when reminded of the reality of his situation and the injustice of his having been imprisoned for life, enters a state of complete dejection. Not to mention the fact that his only friend in the prison, John, is not only leaving, but is getting off on a much easier sentence than he himself faces.
The promise of freedom continues to hold a tempestuous sway over the two friends. Neither of them can quite fathom what it will mean to be free, but they keep coming back to the subject with a giddy kind of delight. Every time the fantasy of freedom gets closer, however, it becomes too much to fathom, and the joyful mood is broken in some way. John is so overwhelmed by the promise of liberation that any reference to it becomes almost painful.
Winston's narration of John's imminent freedom is not coming from a place of generosity and vicarious excitement, but is actually a twisted method of punishing John for his good fortune. He describes the exaltation of John's release as a way of showing John that he ought to feel guilty about his good fortune, given what Winston is going through. "You stink, John," he says, "You stink of beer, of company, of poes, of freedom... Your freedom stinks, John, and it's driving me mad." Winston shows his cards here, and tells his friend that he is unable to be happy on his behalf, because his envy is so strong.
Beyond the oppressive conditions in the prison, there is also the longterm psychological toll the island takes on the prisoners, as Winston explains in his impassioned speeches in this section. More specifically, Winston fixates on the toll that a life sentence takes on a prisoner's memory. He talks about an older inmate who has been imprisoned for life and has no psychological connection with the past or his previous life. Winston even admits that he himself has already begun to forget why he is there, the political ideals he fought for outside the prison, and his life prior to being imprisoned. At the end of the interaction he warns John "Forget me...because I'm going to forget you. Yes, I will forget you. Others will come in here, John, count, go, and I'll forget them. Still more will come, count like you, go like you, and I will forget them. And then one day, it will all be over."