Winston writes in his diary, revealing the details of a particularly sordid night when he had sex with a prole prostitute with a face thickly painted in makeup (which Party women never wear). Winston struggles with his internal turmoil surrounding this disdainful act, noting to himself that man's nervous system is his worst enemy. There is no way to fight involuntary facial spasms or talking in one's sleep. These are the actions that cannot be stopped, yet can condemn one to death.
Winston remembers his wife Katharine, whom he separated from but never divorced, as per Party practice. Winston describes how the Party works continually to remove all pleasure from sexual acts, seeing eroticism as an enemy. Party marriages must be approved by a committee, and to gain such approval, the man and woman in question must not demonstrate any true physical affection for one another. The goal of a marriage is to produce offspring, not to seek personal pleasure or satisfaction. In fact, certain Party organizations, including the Junior Anti-Sex League (of which the dark-haired girl is a member, as demonstrated by the crimson band around her waist), advocate celibacy and procreation through artsem, Newspeak for artificial insemination, and even suggest that children should be raised in public institutions rather than by parents.
Katharine and Winston separated almost eleven years ago, and Winston rarely thinks of her. He nicknamed her "the human soundtrack" because of her empty mind and willingness to spout Party propaganda. Katharine had always been extremely cold when it came to sex, but insisted that she and Winston must keep trying to have children so she could fulfill her "duty to the Party".
Winston returns to his story of prostitution, revealing that when he turned on the light to look at the nakedness of the woman he was about to have sex with, he realized that she was old. She had no teeth at all, and was at least fifty, but Winston completed the act nevertheless. In writing this admission, Winston struggles, pressing his fingers against his eyes and using every vestige of control to avoid screaming foul words.
Some time later, Winston writes, "If there is hope, it lies in the proles." The proles, who comprise eighty-five percent of Oceania's population, are the only ones, he believes, who can overthrow the Party. It is impossible to do so from within. Winston remembers walking down a street and hearing what he thought was a riot - a prole rebellion. In fact, it was women fighting over a limited supply of poorly made frying pans that broke in half during the scuffle. Winston writes, "Until they become conscious they will never rebel, and until after they have rebelled they cannot become conscious." Acknowledging this catch-22, Winston reflects on how the Party has claimed to have liberated the proles from the bondage and slavery of capitalist society, when in actuality the proles still live in squalor, work, produce children, drink beer, and die by age sixty. The Thought Police are always among them, seeking out those deemed too intelligent or too aware of the Party's activities, and removing them from society.
Winston takes a copy of a children's history textbook he obtained from Mrs. Parsons out of his desk drawer and begins to copy a passage describing the ills of capitalist society, including starving children having to work for cruel masters, and capitalist men always wearing long black coats with top hats. Winston then remembers other historical matters he has been taught about the capitalist past, including jus primae noctis, which supposedly was a "law by which every capitalist had the right to sleep with any woman working in one of his factories." Winston notes it is impossible to tell how many of these stories are lies, as nothing can be proved or disproved. Only once in his life has Winston ever held actual proof that Party history is false in his hands.
In the mid-sixties, during a series of great purges removing the original Revolutionary leaders, three men named Jones, Aaronson, and Rutherford were arrested. Under torture, they confessed to a variety of crimes. They were then released and returned to posts within the Party. Winston once saw them at the Chestnut Tree Cafe, and their spirits seemed entirely broken. While he observed them, a song came on over the telescreen: "Under the spreading chestnut tree, I sold you and you sold me..." Shortly afterwards, the three were rearrested and charged with a new string of crimes. Five years later, in 1973, Winston was at work and a newspaper clipping describing the three men at a function in New York on the date that they had confessed to being in Eurasia came into his workstation along with other rolled pieces of paper. Winston held in his hand concrete evidence of their innocence. Ten minutes later, Winston dropped the clipping into the memory hole, destroying it forever. But he never forgot the experience.
Remembering this day, Winston writes "I understand HOW: I do not understand WHY." He wonders if he is alone in this belief that the Party alters history, sometimes for entirely unknown reasons. He wonders if he is a lunatic, and whether it is possible to know that anything is true. Recalling O'Brien's face, he realizes he is sane. With new courage, he writes, "Freedom is the freedom to say that two plus two make four. If that is granted, all else follows."
After work one night, Winston finds himself wandering through the streets of London, among the proles. After being warned, he survives a "steamer" (rocket bomb) attack, a common occurrence in London, which constantly suffers such attacks. Following the attack, he continues his walk and finds himself near the antique shop where he bought his diary and the stationary shop where he bought his pen and ink. Across the street, he sees a very old man enter a pub and decides to take the risk of following him in and asking him about life before the Revolution.
In the pub, the old man keeps asking the bartender for a "pint," and the frustrated bartender keeps explaining to him that there are only liters and half-liters for sale. He does not know what a "pint" is. Winston buys the man a drink and begins to ask him pointed questions about the past and how things have changed since the Revolution. The man acknowledges living before the Revolution, but only refers to life before the Revolution with references to minute details of his life that Winston does not find particularly interesting or satisfying, such as references to top hats, lackeys, and his luck with women. The man simply does not answer Winston as to whether life was better before or after the Revolution.
Frustrated, Winston leaves and finds himself in front of the antique shop. He walks in, thinking he can claim that he is looking for razor blades if he is questioned. The owner of the store, Mr. Charrington, is a frail man of about sixty years old with benevolent eyes, thick spectacles, white hair, and bushy eyebrows. Winston notes that he has a "vague air of intellectuality" about him. The man remembers when he was last in the store, buying the rare diary, or, as he calls it, the "young lady's keepsake album." Winston wanders through the shop and finds a paperweight with a piece of coral inside of it. Winston is struck by its beauty and decides to purchase it. Mr. Charrington suggests that Winston take a look at another room, above the shop. The room consists of a strip of carpet, a few pictures, an armchair, a fireplace, an old-fashioned twelve-hour clock, and a large bed. With amazement, Winston realizes that there is no telescreen. The man explains that he never had a need for one, and begins to show Winston a picture on the wall of St. Clement's Dane. He recites part of a nursery rhyme about the old church: "Oranges and lemons, say the bells of St. Clement's...You owe me three farthings, say the bells of St. Martin's" He cannot remember the rest of it, but knows that the rhyme included the names of all the London churches.
Winston eventually extricates himself from Mr. Charrington and leaves the shop. He wanders home, briefly wondering what it might be like to rent the upper room from the old man. While recalling the rhyme Mr. Charrington shared, he suddenly sees the dark-haired girl from the Ministry of Truth on the road in front of him. In a panic, he stands stock still as she quickly walks on. He wanders aimlessly for a few minutes and then stops, wondering if he should turn back, follow the girl, and murder her with the paperweight to prevent himself from being turned in to the Thought Police. He quickly abandons the idea, thinking himself too weak, and heads home. Once back in his apartment, he chides himself for being so fearful and not acting to protect himself. He writes the rhyme down in his diary and begins contemplating what will happen to him when the Thought Police do eventually come to take him away. He will be tortured; his bones will snap; he will bleed and scream in pain. He thinks of O'Brien saying, "We will meet in the place with no darkness." In his train of thought the image of Big Brother merges and then replaces that of O'Brien. He pulls a coin from his pocket to look at the face of Big Brother, and is instead confronted with the Party slogans: "War is Peace," "Freedom is Slavery," and "Ignorance is Strength."
Through Winston's painful memory of his experience with an aged prole prostitute, we begin to understand the depths of the Party's sexual repression. The memory pains Winston. Because he was so desperate for a close sexual experience, he continued the encounter even after realizing that the heavily made up woman was toothless and old. The Party represses all sexual acts in an effort to force Party members to channel all of their energy into furthering its own goals and needs. The Party must approve all marriages, and such unions must not appear to be sought because of sexual attraction. Sexual pleasure is an individual act, promoting independent thought and independent experiences. Clearly, sex is required for procreation, but through organizations such as the Junior Anti-Sex League, the Party turns sex into a duty performed purely to continue the Party and propagate the human race rather than an act performed for personal pleasure. Winston's wife Katharine felt this way, and was frigid in the bedroom, much to Winston's frustration and humiliation. As we later learn, the Party even encourages abstinence and advocates procreation only through artificial insemination.
The children's textbook (undoubtedly published in the Ministry of Truth) Winston has obtained is particularly revealing of the Party's revisionist history. The Party demonizes capitalism and capitalists, and Winston does not know what information in the book is true and what is false. Winston's story of the newspaper clipping proving Jones, Aaronson, and Rutherford's innocence further evidences the degree to which he yearns for information about the past. Although Winston destroyed the clipping, he knows that it existed, and he knows that the Party covered it up. Here, he addresses an important question that will continue to arise throughout the novel, and will only be answered in the Ministry of Love: Why? He understands how the Party revises history, but does not understand why this constant revision is necessary.
When Winston travels out into the prole world, we begin to see how the rest of the Oceanian population lives. The proles are destitute, living in poverty in areas removed from Party business and life. The prole areas are also the only places Winston and the others can go if they wish to find relics of the past. Winston notably visits Mr. Charrington's antique store, purchases a paperweight, and dreams about what it might be like to live in the apartment above the shop, free from the eyes of a telescreen. Winston is in awe of Mr. Charrington's shop, and wishes he could soak in the history of his artifacts. Winston sees great freedom in the prole world, and it is for this reason that be believes that if there is hope, "it lies with the proles." Unfortunately, the proles seem unable to capitalize on their freedoms, and take no interest in Party affairs.
When Winston meets the old man in the bar, we see the stark contrast between his hopes for a prole rebellion and the reality of prole existence. Winston hopes that the old man will reveal ideological differences between life before the Revolution and life under Party control. However, the man focuses only on very personal memories that do not speak to Winston's concerns. Winston becomes frustrated in this conversation because he believes that the proles, who are not subjected to doublethink and the revision of history, hold the true details of history, and therefore the hope for a brighter future.
When visiting Mr. Charrington, Winston sees the picture of St. Clement's Dane for the first time. This picture, and its accompanying rhyme, become symbols of the past for Winston. He holds onto this picture, and to the first few lines of the rhyme that Mr. Charrington remembered, believing that they represent his ideal of incontrovertible truth and rebellion against the Party. The Party cannot control this picture, or this poem. Despite the hope Winston places in this object and this rhyme, both foreshadow his downfall. The rhyme ends with the line, "Here comes a chopper to chop off your head," and much later we will learn that a telescreen is hidden behind the picture. Winston's walk through this prole area of the city further confirms his rebellion, and continues to set him on the path towards eventual arrest and defeat.