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It starts on a cold, bright day in April 1984. At one p.m., Winston drags himself home for lunch at his apartment.
Winston drinks a bit of Victory Gin and smokes a Victory Cigarette.
Seeing that the alcove in his apartment is hidden from the view of the telescreen, Winston starts writing a diary in the alcove.
Winston’s varicose ulcer itches.
A bit drunk, Winston writes "DOWN WITH BIG BROTHER" in his diary, caps and all, and from that point on he knows that his death is inevitable.
Winston hides the diary.
Winston’s lunch is over as he returns to work by two-thirty p.m.
Winston dreams about the past, his mother’s disappearance when he was ten or eleven, the alluring brunette at his workplace, and Shakespeare – though he does not why.
Winston is awakened by a whistle from the telescreen at seven-thirty a.m., the time at which all workers must rise. He goes into a coughing fit, his ulcer swells and itches, and he does the routine morning exercises the telescreen orders him to.
While Winston exercises, he tries very hard to remember as much as he can about the past. His reflections lead him to doubt the Party’s authority on certain matters, such as who it was at war with at any given time, and when it self-instated as the ultimate power.
Although Winston’s memory of the past is blurry at best, he concludes that he had never heard the word "Ingsoc" before 1960, therefore, the Party could not have been omnipresent as it claims. Winston gets annoyed at the futility of his thoughts, however, because he knows that he can prove nothing, what with the lack of verifiable and confirming documentary evidence and all.
Winston’s job consists of the never-ending alteration of print sources to ensure that they are in agreement with the Party’s version of past and present events.
As a result of Winston’s job, he deems any facts regarding the past, the present, or the future of Oceania to be completely uncertain.
Winston muses that once an act of forgery or spoliation is forgotten, the once made-up subject exists just as authentically as anything else.
Winston has lunch in the canteen with coworker/comrade Syme, who works in the Research Department. Syme is a genius of sorts, but too smart for his own good. Winston imagines that Syme will be vaporized someday.
Syme and Winston discuss Syme’s work on revising the Eleventh Edition of the Newspeak dictionary.
The brunette coworker Winston fancies but hates suddenly stares at him in the canteen, which leads Winston to suspect that she is part of the Thought Police and knows about the thoughtcrime he had already committed.
Winston writes in his diary about his encounter with the prostitute in 1981, his fifteen-month marriage with Katharine, whose whereabouts have been unknown since approximately nine to eleven years ago, and the Party’s denouncement of physical attraction and sex for pleasure.
Winston decries the unthinking, brainwashed followers of the Party, such as Katharine, as he continues to reminisce about sex with her, which she saw only as a "duty to the Party" to make baby comrades.
Winston wants nothing more than to be loved, but realizes that that desire constitutes thoughtcrime.
Winston writes in his diary that if there is hope in overthrowing Party rule, then it lies in the proles, the disregarded masses comprising 85% of the population of Oceania, becoming conscious of their own strength.
Winston looks through a children’s history book, and copies the passage about capitalists into his diary.
Winston now recalls an occasion when he had proof that the Party was changing history. But he kind of dropped the ball on that one.
Winston realizes the futility of physical evidence, and wonders whether the mind itself is controllable. He refuses to believe that it is.
Winston takes a stroll through prole streets, and envies the lives of the ignorant and the free.
He wanders into a pub for beer, and strikes up a conversation with an old man about life pre-Party. The old man is too incoherent to give a satisfactory answer.
Winston passes by the secondhand store in which he bought his diary. We meet Mr. Charrington, a 63-year-old widower who has owned the shop for some 30 years. Winston purchases a glass paperweight containing pink coral to which he is strangely drawn because of its lack of function and its link to the past.
Chatting with Mr. Charrington, Winston is soon led upstairs to a room in which the owner and his deceased wife used to live, but is now abandoned. Seeing that no telescreen exists on the wall (indeed, there is only a print of St. Clement’s Church hanging where a telescreen ought to be), Winston ponders the possibility of renting this room so he can be alone in private.
On his way home, Winston encounters a Party member in blue overalls (Party uniform), and sees that she is the brunette coworker. This confirms for him that the she MUST have been spying on him. Frightened, he temporarily contemplates murdering her with the paperweight in his pocket.
He finally returns home at ten p.m., relieved but restless. He tries to write in his diary, but in his jolted state, he has little success other than jotting down the Party slogans.
Winston leaves his cubicle at work to go to the restroom. Four days have passed. He encounters the brunette "spy" in the corridor – she falls, hurting her arm, and passes him a scrap of paper folded into a square. The note says, "I love you."
Winston suddenly feels an intense desire to live.
After two days, Winston manages to sit at the same table in the canteen as the brunette, and they quickly arrange to meet each other among the crowds at Victory Square at seven p.m. that evening.
When they meet, the thick crowd hides their movements from the telescreens, and the brunette gives Winston precise directions to a place where they can be alone the next Sunday at three p.m. They briefly hold hands, hiding amidst the crowd.
That Sunday, Winston follows the brunette’s directions and the two meet in the countryside amidst bushes, away from telescreens and hidden microphones. The brunette kisses Winston, and tells him that her name is Julia. Winston feels confident with the hiding place, given Julia’s apparent experience.
Julia tears off her Junior Anti-Sex League sash and shares a small slab of luxury chocolate with him. They continue walking through the bushes into the woods.
In the woods, Julia tears her overalls off, flings them aside, and does the deed with Winston.
Winston asks whether Julia has had sex before. She answers that she’s done it scores of times and always with Party members. Winston responds that the more men she has been with, the more he loves her.
The two lovers fall asleep.
Upon waking up, Julia instructs Winston on how to return to London.
Over the coming weeks, the two arrange several meetings but only succeeded in making love once during the month of May.
The two muse about the reasoning behind the Party’s anti-sex campaigns and about parenting.
Winston rents the room above Mr. Charrington’s secondhand shop for private times with Julia. The pair has been preparing for Hate Week at work, and because of the longer working hours, Winston has become increasingly frustrated over their inability to meet during the month. Julia has become a physical necessity for him. Winston daydreams about growing old and living a carefree life with her.
He has sex with Julia and falls asleep again.
Winston proclaims that rats are is his biggest fear.
Winston prepares for and participates in Hate Week.
Winston reflects that he met with Julia at least seven times during the month of June, and the love affair alleviated the symptoms of his varicose ulcer, his coughing, and his need for alcohol. He and Julia’s impending death (due to their criminal affair) troubles Winston. He fantasizes that Katharine will die so he can remarry, and even about changing their identities to become and live like proles.
Winston and Julia speak about politics and the Brotherhood. But Winston is annoyed by Julia’s selfish concerns and lack of lofty, rebellious goals.
O’Brien makes what Winston believes to be subversive contact with him in the corridor at the Ministry of Truth. Winston is all eager and excited.
O’Brien discusses with Winston the tenth edition of the Newspeak dictionary, and tells him that he can take a peek at it if he makes a visit one evening.
Winston awakes one morning in the room atop Mr. Charrington’s shop, crying. He tells Julia about his dreams of the past – repressed memories of his childhood revealed. Up until this moment, Winston has believed that he had murdered his mother, but the dream clarified that he in fact, in all likelihood, did not.
Winston tells Julia that the Party has made them inhuman by severing familial ties and loyalties, and by its attempt to alter histories.
Winston and Julia discuss their steps going forward, given O’Brien’s contact. The two acknowledge the possibility of torture and death if they are captured. They agree not to betray one another.
Winston and Julia arrive at O’Brien’s luxurious flat.
Winston and O’Brien converse about Goldstein, the conspiracy, and the underpinnings of the workings of the rebellious forces. O’Brien tests the pair’s commitment to the Brotherhood.
O’Brien questions Winston about his hiding place and tells him about the importance of Goldstein’s book.
Winston and O’Brien repeat the old rhyme about St. Clement’s Church.
Winston reads Goldstein’s The Theory and Practice of Oligarchical Collectivism, the anti-Party manifesto.
Julia joins him in their private sanctuary. He reads to her.
The two fall asleep.
Winston and Julia awake at eight-thirty p.m. The two discuss how the future depends on the proles and their progeny. They realize that they are the dead.
From behind the picture of St. Clement’s Church, Mr. Charrington’s voice repeats, "You are the dead." The two realize that a telescreen is hidden behind the picture, and soon stomping boots surround the house.
Winston is beaten and then taken away by the Thought Police.
Winston wakes up in a bright, high-ceilinged, windowless cell at the Ministry of Love.
Winston first meets a large prole woman who shares his last name, Smith. Both contemplate the possibility of her being his mother.
Winston briefly meets a poet, Ampleforth, who was incarcerated for the crime of leaving the word "God" in a Kipling translation. Before long, Ampleforth is dragged off to a mysterious place called "Room 101."
Winston then sees his neighbor and coworker, Tom Parsons, whose daughter chewed him out to the Patrols upon hearing his blabbering "down with Big Brother!" in his sleep.
Winston then meets the man dying of starvation, named "2713 Bumstead J." He is beaten brutally when he tries to accept a piece of bread from Winston, and is then sent to Room 101.
Winston is completely discombobulated, not knowing how much time had passed nor even the time of day. He dreams about saving Julia by agreeing to double the amount of pain allotted to him, and wishes the Brotherhood would send him a razorblade so he could off himself.
Finally, O’Brien enters Winston’s cell, and self-introduces as the chief operator of the Ministry of Love. Winston is crushed, and a guard uses the truncheon to disable Winston’s left arm. So begins his journey of physical torture.
Subjected to prolonged torture, Winston (like all the other prisoners) confesses to an extensive range of crimes – espionage, sabotage, and the like.
At O’Brien’s direction, Winston is strapped onto a torture machine that is designed to stretch backbones until they break.
Winston becomes brainwashed.
After weeks or maybe months of torture, Winston is forced by O’Brien to look in the mirror for a picture of "humanity." Winston cries upon seeing his deterioration; he looks to be 60 years of age with the grayness, emaciation, and bent spine.
Winston lashes back, and O’Brien recognizes that he still hasn’t betrayed Julia.
After weeks or maybe months, the tortures eases and Winston grows fatter and stronger.
Voluntarily, Winston tries to make himself believe in Party slogans, to learn to be stupid.
One night, he screams out Julia’s name in the middle of a nightmare. Guards come for him, and he realizes that he has a new goal: to die hating the Party, as that will be a wee victory.
Winston faces O’Brien, and tells him he hates Big Brother. To Room 101 with you, Winston!
O’Brien threatens Winston by showing him a cage of large, vociferous rats, waiting to gnaw away at Winston’s face.
Winston, with the rats just inches away from his face, is terrified. He cries out, "do it to Julia!"
Winston is released.
At three p.m. one day, months later, Winston sits at the Chestnut Tree Café, where dismissed Party members go to have gin. He is content, is working as a sinecure, and accepts all that the Party says and does.
He reminisces about the time back in March, 1985 when he saw and spoke with Julia again.
Winston felt nonchalant about her. They spoke of their mutual betrayal and how torture can change people. They agreed to meet again, though neither intended to carry that out.
Winston cries. He remembers happy family life with his mother and sister, but wonders if it is a false memory; he listens to the telescreen spewing propaganda that he now truly accepts.
He daydreams about his time at the Ministry of Love, and further about the promised bullet that is destined to enter his brain. He looks up at the picture of Big Brother on the telescreen, and feels joy over his love for him and the great victory he has won over himself (as a traitor).