Newland goes to Madame Olenska's small, rented house "far down West 23rd Street," in a strange, Bohemian quarter. The Countess is not home, so Newland has ample time to look around her drawing room. The room is intimate and exotic, unlike the staid, conservative rooms of his life. He realizes that his and May's future drawing room will be nothing like this; it will be traditional and conservative. Eventually The Countess Olenska arrives with Julius Beaufort who leaves her at her door. She is house hunting because her family will not let her stay where she is even though the street is respectable. Newland counters that it is not "fashionable." Madame Olenska's candor is expressed when she tells Newland, "why not make one's own fashion?" Throughout their conversation she states candid opinions and he is shocked by her frankness. He tries to warn her that New York society does not like honesty, and she should be listening to her female relatives for advice. He would like to warn her to refrain from driving with Beaufort, but he prudently keeps silent. The Countess wins his sympathy when, sobbing, she explains how lonely she is. During her distress Newland forgets formalities and calls her "Ellen" twice, and then guiltily remembers May. The Duke of Astrey and Mrs. Struthers arrive, and she invites Madame Olenska and Newland to her salon on Sunday. Madame Olenska agrees, but Newland is silent. Leaving, Newland stops at a florist shop to order May's daily lilies of the valley. Seeing richly hued, yellow roses, he considers sending them to May; but instead, without his card, he sends them to the Countess.
Newland's conflict continues. On a Sunday walk with May, he mentions sending roses to Ellen; May finds it odd that Ellen did not mention them. Again, he and May discuss the wedding date, and Newland is struck by May's lack of imagination or original thought. Their conversation leads him to regret the sameness of everything, including her expected reactions to his expected comments. The next afternoon Janey announces to Newland that Mrs. Archer is agitated because Madame Olenska has been seen at Mrs. Struthers' with the Duke and Julius Beaufort. In the midst of the argument, Henry van der Luyden arrives, explaining that he went to see the Countess Olenska to pass along some friendly advice. He says that the Duke does not realize "our little republican distinctions" and is leading Madame Olenska into mischief. Because the Duke was a guest in his house, van der Luyden feels he must explain the Duke's actions in an acceptable manner. Likewise, because Madame Olenska told Mr. van der Luyden that she would be grateful for his guidance, he has defended her to Sillerton Jackson.
Newland works at the legal firm of Letterblair, Lamson, and Low. His boss, Mr. Letterblair, asks him to represent the Mingott family in dissuading the Countess Olenska from seeking a divorce. He gives Newland two letters to peruse, one from a French legal firm about finances and the other from the Count. A deadly quiet dinner with Mr. Letterblair emphasizes scandals that have brought down families and Newland's boss states three points: the Mingott family is against divorce, the Countess does not want the Count's money, and it would be wise to avoid a scandal that could only hurt the Countess and the Mingotts. Newland reluctantly agrees to take the case, but refuses to solidify his stance on the divorce until he has spoken to Madame Olenska. He sends her a note and she agrees to talk to him.
