O'Brien then lists a series of horrific crimes that Julia and Winston might be required to commit by joining the Brotherhood. Julia and Winston admit that they are willing to carry out the various crimes but refuse to separate or leave each other's side. O'Brien goes on to explain the costs of being a member of the Brotherhood and assures them that they will never live to see the destruction of Big Brother. He then discusses the makeup of the Brotherhood and explains that there is no way of telling how many members are part of the secret organization.

O'Brien also explains that nothing holds the organization together except an indestructible idea and assures Julia and Winston that they will eventually be captured by the Thought Police. However, there is hope that another member of the Brotherhood might be able to smuggle a razor blade into their prison cell before they are tortured. Julia, Winston, and O'Brien then raise their glasses of wine and toast to the past. O'Brien then promises to give Winston a copy of THE BOOK and recites the last line of the traditional English nursery rhyme before they exit the apartment.

O'Brien then elaborates on the seriousness of becoming a member of the Brotherhood and mentions that Julia and Winston "will be fighting in the dark." According to O'Brien, Julia and Winston will receive orders and must follow them blindly without understanding why. He also mentions that he will be their only contact and explains that the Brotherhood is a loose, ambiguous organization, which makes it impossible for the Party to destroy it. O'Brien then informs Julia and Winston that they will never witness any "perceptible change" or progress in their entire lives and mentions that the Brotherhood's primary goal is to spread "knowledge outwards from individual to individual, generation after generation." Before Winston leaves, O'Brien promises to supply him with a copy of Emmanuel Goldstein's book and gives him instructions to pick it up.

In Part 2, Chapter 8, Winston and Julia go to see O'Brien at his luxury apartment. O'Brien is a member of the Inner Party and so enjoys special privileges unavailable to those outside this charmed circle. When they finally meet Winston confesses to O'Brien that he and Julia are both enemies of the Party. Winston's trust in Julia has given him the confidence to trust O'Brien as well. All three drink wine and make a toast to the past, demonstrating their hatred for the Party and its rule.

O'Brien reveals the existence of a secret Brotherhood, an underground insurrectionary group dedicated to the overthrow of the Party. The Brotherhood is inspired by the ideas of Emmanuel Goldstein, a mysterious oppositional figure who represents the antithesis of Big Brother. Yet, no one knows for sure whether he actually exists. But O'Brien assures Winston that Goldstein is indeed a real person. He promises to send Winston and Julia a book written by Emmanuel Goldstein which will spell out in precise detail how the Party can be destroyed. Then, they will become members of the Brotherhood.

As Winston leaves he asks O'Brien if they will meet again "in the place where there is no darkness," a suitably ambiguous expression which foreshadows much of what is about to happen. O'Brien also knows an old nursery rhyme which indicates to Winston that he's genuinely opposed to the Party, as such historical knowledge is strictly forbidden in the totalitarian state of Oceania.