Chapter 21: Wemmick introduces Pip to Herbert Pocket and Pip will spend the night. Herbert and Pip like each other immediately. Herbert is cheerful and open, and Pip feels that his easy good nature is a contrast to his own awkward diffidence. Whereas Pip’s already has money, Herbert is an impoverished gentleman who hopes to become a shipping merchant. They realise Herbert is the pale young gentleman whom Pip fought in the garden at Miss Havisham’s house.

Chapter 22: Pip asks Herbert to help him learn to be a gentleman and the two agree to live together. Herbert corrects Pip’s poor table manners, gives him the nickname “Handel,” and tells him the whole story of Miss Havisham. It was assumed that Miss Havisham’s lover was in league with her half brother and that they split the profits from the brewery sale. At some later point, Miss Havisham adopted Estella, but Herbert does not know when or where.

Chapter 23: The next day, Pip visits the unpleasant commercial world of the Royal Exchange before going to Matthew Pocket’s house to be tutored and to have dinner. The Pockets’ home is a bustling, chaotic place where the servants run the show. Matthew is absentminded but kind, and his wife is socially ambitious but not well born; the children are being raised by the nurse. Pip’s fellow students are a strange pair: Bentley Drummle, a future baronet, is unpleasant, and a young man named Startop is soft and delicate. At dinner, Pip concentrates on his table manners and observes the peculiarities of the Pockets’ social lives.

Chapter 24: Pip returns to Jaggers’s office in order to arrange to share rooms with Herbert. There Wemmick invites Pip to dinner. Pip sees Jaggers in the courtroom, where he is a potent and menacing force, frightening even the judge with his thundering speeches.

Chapter 25: Pip continues to get to know his fellow students and the Pockets, attending dinners at both Wemmick’s and Jaggers’s. Wemmick’s house is like something out of a dream, an absurd so called castle in Walworth that he shares with his aged parent. Pip observes that Wemmick seems to have a new personality when he enters his home which is jovial and merry.

Chapter 26: Jaggers’s house is dark, shared only with the housekeeper, Molly. Pip’s fellow students attend the dinner at Jaggers’s with Pip, and Pip and Drummle quarrel over a loan Drummle ungratefully borrowed from Startop. Jaggers warns Pip to stay away from Drummle, though the lawyer claims to like the disagreeable young man himself.

Chapter 27: Joe comes to visit Pip in London. Because Pip worries that Joe will disapprove of his opulent lifestyle and that Drummle will look down on him because of Joe, Joe’s visit is strained and awkward. He tries to tell Pip the news from home: Wopsle, for instance, has become an actor. But Pip acts annoyed with him until Joe mentions that Estella has returned to Satis House and that she wishes to see Pip. Pip suddenly feels more kindly toward Joe, but the blacksmith leaves before Pip can improve his behaviour.

Chapter 28: Hoping to see Estella and to apologize to Joe, Pip travels home, forced to share a coach with a pair of convicts, one of whom is the mysterious stranger who gave Pip money in the pub. Though this man does not recognize Pip, Pip overhears him explaining that the convict Pip helped that long-ago night in the marshes had asked him to deliver the money to Pip. Pip is so terrified by his memory of that night that he gets off the coach at its first stop within the town limits. When he arrives at his hotel, he reads a notice in a newspaper, from which he learns that Pumblechook is taking credit for his rise in status.#

Chapter 29: When he travels to Satis House the next day, Pip pictures himself as a triumphant knight riding to rescue the Lady Estella from an evil castle. He encounters Orlick, now Miss Havisham’s porter, at the gate. When he sees Estella, he is stunned: she has become a ravishing young woman. Despite his newfound fortune, Pip feels horribly inadequate around her, as unworthy and clumsy as ever. Miss Havisham goads him on, snapping at him to continue to love Estella. Pip walks with Estella in the garden, but she treats him with indifference, and he becomes upset. Pip realizes that she reminds him of someone, but he can’t place the resemblance. Back inside, he discovers Jaggers there and feels oppressed by the lawyer’s heavy presence.

Chapter 30: The next day, Pip tells Jaggers about Orlick’s past, and Jaggers fires the man from Miss Havisham’s employ. Pip is mocked by the tailor’s apprentice as he walks down the street. He returns in low spirits to London, where Herbert tries to cheer him up, though he also tries to convince him that, even if Miss Havisham is his secret benefactor, she does not intend for him to marry Estella. Herbert confesses to Pip that he, too, is in love and, in fact, has a fiancée named Clara, but he is too poor to marry her.

Chapter 31: Pip and Herbert go to the theatre, where Wopsle plays a ridiculous Hamlet. Pip takes the hapless actor out to dinner following the play, but his mood remains sour.

Chapter 32: Pip receives a note from Estella, ordering him to meet her at a London train station. He arrives very early and encounters Wemmick, who takes him on a brief tour of the miserable grounds of Newgate Prison. Pip feels uncomfortable in the dismal surroundings, but Wemmick is oddly at home, even introducing Pip to a man who has been sentenced to death by hanging.

Chapter 33: When Pip meets Estella, he is again troubled by her resemblance to someone he can’t place. She treats Pip arrogantly, but sends him into ecstatic joy when she refers to their “instructions,” which makes him feel as though they are destined to be married. After he escorts her through the gas lit London night to the house at which she is staying, he returns to the Pockets’ home.

Chapter 34: Pip feels terribly guilty for his snobbish treatment of Joe and Biddy, and he feels as though his degenerate lifestyle has been a bad influence on Herbert. The two young men catalogue their debts, but they are interrupted by a letter carrying the news that Mrs. Joe has died.

Chapter 35: Pip is surprised by the intensity of his sadness about his sister’s death. He returns home at once for the funeral. He meets Pumblechook, who continues to fawn over him irritatingly. He tries to mend his relations with Joe and Biddy; Biddy is skeptical of his pledges to visit more often. Pip says goodbye to them the next morning, truly intending to visit more often, and walks away into the mist.

Chapter 36: Pip’s twenty-first birthday finally arrives, meaning that he is an adult and will begin to receive a regular income from his fortune rather than having to go to Jaggers to access his money. He feels a great sense of excitement, because he hopes that his entrance into adulthood will cause Jaggers to tell him the identity of his mysterious benefactor. Despite Herbert’s warning, he feels increasingly certain that it is Miss Havisham and that she means for him to marry Estella. But during their interview, Jaggers is cold and brief; he reveals nothing about the source of Pip’s fortune, simply telling him that his income will be five hundred pounds a year and refusing to take responsibility for the outcome. For some reason, the encounter reminds Pip of his meeting with the convict in the graveyard so many years before. Still, Pip invites Jaggers to participate in his birthday dinner, but Jaggers’s oppressive presence makes the evening less enjoyable for Pip and Herbert.

Chapter 37: Pip is going to buy Herbert start a merchants business but Wemmick says he would rather throw it off a bridge than invest.