Not long after Mr. Touchett's death, Madame Merle arrives at the Touchetts' London home and discovers that the family is preparing to sell it. Mrs. Touchett tells Madame Merle how happy she is that her husband has left her financially secure; Merle is extremely jealous, though she keeps her feelings guarded. When she learns that Isabel has also inherited a fortune, she says that Isabel is very clever and hurries in to see her. Since Mr. Touchett's death, Isabel has spent a great deal of time thinking about her wealth and what it means; she has decided to be grateful for the freedom her money will afford her.
Isabel soon travels to Paris with Mrs. Touchett, but she finds her aunt's American friends there to be depressingly American. She encounters Henrietta, who is traveling happily with Mr. Bantling. Henrietta says that she disapproves of Isabel's new fortune—she thinks that it will allow Isabel to continue living in a world of dreams and ideals. Henrietta insists that Isabel should worry less about pleasing others and concentrate on facing hard truths about the world.
Mrs. Touchett offers Isabel the choice about whether to travel with her to Italy for the autumn, saying that, now that Isabel is rich, she may do as she pleases. Isabel, out of respect for social conventions, chooses to go to Italy with her aunt. On the way to Florence, they stop in San Remo, where Ralph is staying. Isabel and Ralph discuss her new fortune; Ralph admits that he knew about his father's decision to change his will before he died. Isabel worries that Henrietta is right and that the fortune will be bad for her. Ralph encourages her to embrace the things that happen to her and enjoy her new wealth. His advice reassures Isabel, and she begins to look forward to her trip to Italy, which seems like a great adventure. Thinking of Warburton and Caspar, she wonders if either of them will marry; she thinks that she would feel hurt if Caspar fell in love with another woman but that she would be glad if Warburton did.
Six months after Mr. Touchett's death, Gilbert Osmond meets his daughter Pansy and a group of nuns at his home near Florence; he discusses with the nuns the possibility that he might take Pansy away from their convent and bring her to live with him. He is joined by Madame Merle, who tells him about a beautiful twenty-three-year-old girl named Isabel Archer, who has inherited half the Touchett fortune. She promises to bring Isabel into Gilbert's orbit and says that she wants him to marry her. Gilbert says that Merle is a remarkable woman, but he has no interest in marrying. Merle insists, reminding him that he has no money of his own, and Isabel's fortune could provide a dowry for Pansy. As she watches Pansy playing outside, Merle notes dryly that the girl does not like her.
Not long thereafter, Merle arrives for a month-long visit at the Palazzo Crescentini, Mrs. Touchett's home in Florence. She fills Isabel's ears with flattering descriptions of Gilbert Osmond; eventually, Osmond pays a visit and invites Isabel to visit him at home and meet his daughter. During the visit, Isabel is strangely withdrawn; she is impressed with Osmond's refined manner, and he seems to catch her imagination. Isabel talks to Ralph about Osmond; Ralph says that he is indeed very refined but seems to have no other qualities. But he reminds her that she should judge people for herself.
They discuss Madame Merle, and Ralph tells Isabel that he dislikes the older woman's apparent perfection—she is too devoted to maintaining the impression that she has no flaws. Inwardly, he thinks that Isabel's friendship with Merle will not harm Isabel; one day, he thinks, Isabel will see through Merle and, in all likelihood, will lose interest in her.
Not long after this conversation, Merle takes Isabel to visit Gilbert Osmond's house; looking at the imposing villa from the outside, Isabel has the impression that once you were inside, it would be very difficult to get out. Inside, she meets the Countess Gemini, Osmond's annoying sister; she talks incessantly, and eventually Osmond draws Isabel aside while Merle keeps the Countess entertained. He tells Isabel that his sister is unhappily married and that she covers up her pain by acting foolish.
As Osmond describes his life—he says that he has sacrificed everything but his devotion to art and good taste—Isabel is again impressed with his refinement and his obvious taste. In fact, as he shows her his paintings, she works very hard to say the right things about them; like no one she has ever met, he makes her feel a need to measure up. He tells her that, though he has lived a life of renunciation, he will soon need to find a source of income, because he must provide for his daughter.
This section initiates a new phase of the novel, which centers on Isabel's wealth and Merle's scheme to marry her to Gilbert Osmond. This scheme becomes more and more obvious to the reader throughout this section, just as it remains entirely opaque to Isabel, who believes that Merle is her friend and that Osmond is the wonderful and brilliant man Merle says he is. To virtually every other character in the book, Osmond is unremarkable, pretentious, and selfish; Ralph dislikes him very strongly. But Merle presents Osmond to Isabel as one of the finest gentlemen in Europe, who has cast off the bonds of society and chosen to live for his art. Because Osmond also seems cleverer than Isabel, her romantic side is deeply drawn to him.
James uses a number of literary techniques to make certain that the reader will find Osmond and Merle increasingly sinister throughout these chapters. One technique is a character's unconscious exclamation: in Chapter 20, for instance, when Merle learns that Isabel has inherited her fortune, she unintentionally blurts out that Isabel is "clever." She immediately covers up her mistake, but this exclamation indicates to the reader that Merle assumes that Isabel has manipulated her way into inheriting Mr. Touchett's wealth—hardly a flattering thing to think about someone who is supposed to be your close friend. This seems to indicate that Merle considers manipulation the most likely path to wealth and also that she herself is capable of such manipulation. It follows that she will attempt to manipulate Isabel into gaining access to her newfound wealth.
Another literary technique James uses to make Osmond seem unsavory is to make his surroundings seem ominous: Isabel finds Osmond extremely attractive, but she is unsettled by the sight of his house, which seems prison-like to her, as though, once in, it would require a force of will for a person to get out. (Prison imagery is associated with Osmond throughout Portrait of a Lady, especially as regards his treatment of Pansy.) Throughout the novel, James implies a strong correlation between a person's character and the environment of their home: Gardencourt is a loving, beautiful place, and is a symbol of the Touchetts, while Isabel's ramshackle home in Albany perfectly matches her disorganized upbringing and education. Because Isabel finds Osmond's home ominous, the reader finds Osmond himself ominous.
The Portrait of a Lady is a very sedate novel in terms of action: narrative developments occur slowly, and when they do occur, they are rarely exciting in the conventional sense. The novel is given the pace of the upper- class drawing rooms it portrays, and as a result, it is lacking in visceral excitement. One of the ways in which James sustains the reader's interest as his slow-paced story develops is to propose questions and mysteries and then to delay the answers for a great many chapters. Will Isabel marry? What will she do with her independence? Characters are often introduced and then dismissed, and we are left wondering: what will become of Lord Warburton? Of Caspar Goodwood? Of Henrietta? In this way, James keeps the reader reading, even when his plot seems to lack some of the other elements that normally draw people into a work of fiction.
In this section, James introduces the most lasting and most compelling unsolved mystery that occurs in Portrait of a Lady and one that is not explicitly solved until the end of the book: what is the relationship between Madame Merle and Gilbert Osmond? They seem to be very close, to have a long history together, and to work together in certain ways, but their history is not elaborated and their relationship seems very mysterious. What kind of relationship, particularly in sedate nineteenth-century Europe, features a woman manipulating another woman into marrying a man to which she is very close?