Chapter 5: Winston goes to lunch and meets up with his friend Syme, who worked in the Research Department. Technically they weren’t allowed to have friends, you had comrades, but Winston found Syme pleasanter than others. Syme was a philologist, which meant he was a specialist in Newspeak - the official language of Oceania. Along with an enormous team of experts, Syme was working on the Eleventh Edition of the Newspeak dictionary. He tells Winston that by creating Newspeak the range of thought is narrowed, allowing it nearly impossible to commit thoughtcrime. Winston thinks that Syme’s intelligence will eventually lead to him being vaporized one day.

Suddenly, the pudgy Parsons, the husband of Mrs. Parsons whose sink Winston fixed, walked over. He asked Winston for the two dollars he supposedly owed for Hate Week. Parsons then apologized to Winston for yesterday when his son shot him with his catapult toy. Interrupting their conversation was a message coming from the telescreen from the Ministry of Plenty. The announcement was that they have won the battle for production, although Winston recalls that the increase they are talking about is actually smaller than it was the day before. He seems to be the only one to notice, as others accept this news rather pleasantly. 

Winston looked over at another table, where the dark-haired girl from the Fictional Department, was looking at him. When they made eye contact, she looked away, and Winston began to spiral into fearful thoughts wondering why she was watching and following him. He began to worry that if she was not a part of the Thought Police, she might be a spy for the Party meaning she was much more dangerous.

Chapter 6: Back at his loft this evening, Winston was writing in his diary. He was writing about his last sexual encounter which occurred with a prole prostitute. Winston has to keep taking breaks from writing to control himself, as he did not enjoy reminiscing about this memory. He thinks about how the Party disapproved of sex and saw the act as a way that men and women would create loyalties that the Party could not control. Winston was convinced that the Party only wanted sex to be seen as a duty to perform for the Party to produce new Party Members, but also removing any pleasure from the act itself. 

When he begins to think of that woman, he also thinks about his former wife Katherine. Katherine did not enjoy their intimacy, but simply saw it as their duty to the Party to produce a child.  Unfortunately, a child never came and Katherine gave up trying. It had been nearly eleven years since they had parted from one another. The Party didn’t permit divorce, but made exceptions in cases with no children for then they encourage separation. 

Deep down Winston wants to experience an enjoyable sexual relationship, but he sees it as the ultimate act of rebellion against the Party. Winston continues to write about his encounter and exposes the fact that when he turned on the light he saw that the prole prostitute was old and ugly, but he went through with the sexual interaction anyway. He then realized that writing about this incident made no difference in how he felt, no weight had been removed from his shoulders. 

Chapter 7: Winston writes in his diary that if there is any hope for a revolution against the Party, it lies with the proles. The proles consist of 85% of Oceania’s population and would therefore have the numbers to overcome the Party and the Thought Police. He believes that the Party cannot be destroyed from within, and even if the Brotherhood, the legendary group of revolutionaries, did exist they would not have enough to defeat the Thought Police. Although the proles seem to have no need to conspire and rebel because they already live oblivious and voluptuous lives and most of them aren’t even aware that the Party is afflicting them.

Winston then grabs a children’s history book and begins to look through it. He wonders why when the Party is said to have built supreme cities,  then why is London where he lives in decay and wreckage as people live frightened and hungry. Winston starts to suspect that most of the Party’s claims are false such as reducing the infant mortality rate, giving citizens more sufficient food and shelter, and that the literacy rate has increased as well. He can’t be sure if they are untrue though, because he knows that all history was written and modified by the Party itself. 

He then reflects on a time in which he had caught the Party in an act of falsification. It occurred in the mid-1960s after all the original leaders of the Revolution were wiped out, and by 1970 only Big Brother was left. Goldstein had escaped and was hiding, a few of the others disappeared, and a majority were executed. The last survivors were three men named Jones, Aaronson, and Rutherford who eventually came forward and confessed to intelligence with the enemy, embezzlement of public funds, acts of sabotage that lead to massive deaths, intrigues against Big Brother, and various murders of Party members. After confessing they were all pardoned and reinstated in the Party. Winston had actually seen all three of them after their pardon at the Chestnut Tree Cafe, but eventually were rearrested for participating in new conspiracies since their release and were executed. About five years later, Winston came across a document at work that had a photograph of the three men at a Party function in New York when at that time they confessed that they were on enemy soil. Winston realized that their confessions were lies, and although he destroyed that photograph he would never be able to destroy that memory of deceitfulness from the Party.

Winston continues writing in his diary but begins to think of his diary as a letter to O’Brien who he still believes is on his side. The only thing Winston knows about O’Brien is his name, yet he can sense a sort of rebellion in him that is similar to his own. Now thinking about the work that Winston does himself, he realizes that the Party wants to control the truth even if it’s incorrect and to force everyone to agree with and believe whatever the Party tells you to believe. He then realizes that freedom is allowing one to perceive reality and how they portray it themselves.