Volume 2, Chapter 18: The next Sunday Pip goes to Wemmick's "castle" for dinner and is met by the "Aged." Wemmick is not home, but expecting him. After a little bit, Wemmick does arrive home with a woman named Miss Skiffins. Pip and Wemmick take a walk and Pip explains that he wants to find Herbert a position where he can become a partner in a company, and that he is prepared to put capital into the business for this position. Wemmick agrees to help him, and they spend the rest of the evening amicably. A few weeks pass, and they find a perfect position for Herbert who knows nothing of Pip's involvement. After seeing the joy that Herbert experiences, Pip is finally happy with his wealth.
Volume 2, Chapter 19: All during this time, Pip spends time in Richmond with Estella. He escorts her and the women she lives with to parties, and other social gatherings. Many days he sits by and watches her flirt with other men, often using him to make them jealous. One day, Estella tells him that she received a letter from Miss Havisham that asks her to come home for a visit and that Pip is to escort her. Pip agrees although he is miserably in love. On one such occasion, Estella sits with her arm wrapped through Miss Havisham's. Estella begins to pull away, and Miss Havisham gets angry asking why Estella does not love her. Estella then says questions how she is supposed to love when Miss Havisham raised her for the opposite purpose. After a few moments, they make up, and no such thing occurs on subsequent trips. When back in London, Pip attends a "Finches" meeting, Drummle is asked to make a toast to a lady, and he names Estella. Pip angers at this and one night after a ball, approaches Estella about encouraging Drummle. She tells him that she can do whatever she pleases, and he says that she never gives him the looks and smiles that she gives other men. She tells him that she does that to deceive and entrap them, and that he is the only one in which she does not do this.
Volume 2, Chapter 20: Pip turns twenty-three and he is at home one night reading at his lodgings in Garden-court. He and Herbert were still living together but Herbert was on a business trip. One night, while reading he hears someone coming upstairs. An old man comes in with long gray hair and says that he is looking for Mr. Pip. After a few moments of talking to him, Pip realizes that it is his convict. The man tells him that he was a sheep farm in the new world, and that every cent that he earned, he sent to Pip. He was Pip's benefactor and asks for lodging for the night. The convict also tells him that he is still hunted, so they must be cautious. The convict retires to the couch and Pip tries to sleep but is haunted by the facts he learned that evening.