Pip suggests to Mr. Jaggers that Orlick can't be trusted as Miss Havisham's porter. Mr. Jaggers agrees, happily noting that posts of trust are never filled by upright men. To Pip's surprise, Mr. Jaggers' cheerfully announces he'll fire Orlick immediately, unfazed by Pip's fear that Orlick might put up a fight.
Mr. Jaggers' cheerfulness is further evidence of his comfort dealing with people lacking in principles and integrity.
While walking through town, Pip runs into Trabb's Boy, who follows Pip throughout the town making fun of him by feigning intimidation and parodying Pip's snobbish demeanor. Pip feels disgraced and, thinking it would be "futile and degrading" to argue with the boy himself, writes Mr. Trabb a letter informing him that Pip will no longer patronize his business because of the boy.
Trabb's Boy is the only villager Pip encounters who does not fawn over his newly won status and wealth. His taunts deal a blow to Pip's pride, but instead of confronting Trabb's Boy directly, Pip uses his financial might to indirectly punish him.
Pip takes the coach back to London and, immediately upon arrival, sends "a penitential codfish and barrel of oysters to Joe" to make up for not having visited him.
Pip confuses a generous heart with a generous wallet, thinking he can replace one with the other.
Back at Barnard's Inn, Pip tells Herbert about his love for Estella and is shocked to hear Herbert already intuited it. Herbert reveals that he too believes Estella is secretly betrothed to Pip. But when he hears Mr. Jaggers has never mentioned marriage among Pip's expectations, Herbert changes his mind. He advises Pip to detach himself from her because of Estella's background and character, which "may lead to miserable things." Pip agrees, but feels unable to detach himself.
As in all matters concerning Estella, Pip is delusional and doesn't realize how obvious his infatuation with her is to others. Herbert advises Pip to stop loving Estella in order to improve Pip's quality of life, knowing that Miss Havisham's vengefulness has shaped Estella to torture men who love her.
Changing the subject, Herbert confides to Pip that he himself is secretly engaged to Clara, the daughter of a ship's steward who would not live up to Mrs. Pocket's title-obsessed standards. Clara lives with her ailing, foul-tempered father. Herbert says he will marry Clara as soon as he begins to make money.
Herbert has not inherited his mother's obsession with social status and inherited titles—in fact, he wants to distance himself as far from her value system as he can.