Syme (the genius co-worker) has vanished as Winston predicted. Now he has ceased to exist, therefore he never existed.
Winston observes the various preparations for Hate Week: posters, propaganda, Hate songs, and streamers.
Winston reflects that he met with Julia at least seven times during the month of June; all the sex has alleviated the symptoms of his varicose ulcer, his coughing, and his need for alcohol.
Winston briefly thinks about Mr. Charrington, the guy who runs the shop in the prole district and is always down for the small talk. Winston is thankful for the privacy sanctuary Mr. Charrington affords him and Julia. Sounds like more foreshadowing.
Winston is troubled by he and Julia's impending death due to their affair which, in case you forgot, is completely illegal.
He fantasizes that Katharine will die so he can remarry, and even about changing his and Julia's 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. He speaks of questioning the Party's authority, an organized revolution, his intellectual crush on O'Brien, and passing on his efforts to the next generation.