Hurstwood intends to make Carrie "confess an affection for him." His work schedule is flexible, so he takes an afternoon off to see her. They ride a horse-drawn carriage to the prairie outside of Chicago, where he declares that his times with her have been the happiest he has spent in years. He confesses that he loves her and asks that she declare her love for him. She replies with a kiss.
Carrie rejoices in Hurstwood's love for her and agrees to meet again the next Sunday. Mrs. Hale notices that Carrie has been going out riding with another man while her "husband" is away, and the house-maid, who is fond of Drouet, wonders at Hurstwood's two visits while Drouet is out of town. Gossip spreads through the building.
Hurstwood entertains fantasies of "pleasure without responsibility." He does not think he is doing anything that compromises his life. Carrie dines with him on Sunday evening, but she keeps him at a distance, which paradoxically incites his passion even more. They agree to exchange letters in care of the Post Office in order to preserve the secrecy of their affair. Drouet returns from his trip, and Hurstwood tells him that he had called on Carrie once during his absence because he thought she might be lonely.
Drouet tells Carrie that Hurstwood wants to go to the theater with them. Carrie mentions that he called on her twice during Drouet's absence, contradicting Hurstwood's earlier story, but Drouet thinks nothing of it. Carrie and Hurstwood exchange letters and get their stories straight. Carrie is under the impression that Hurstwood plans to marry her as soon as possible. The evening at the theater goes well, and Drouet continues to suspect nothing. A beggar stands outside the theater asking for money to rent a room for the night. Drouet is the first to notice, and he gives the man some money. Hurstwood scarcely notices, and Carrie quickly forgets.
Hurstwood begins to regard his home life with even greater indifference than before. Julia demands a season ticket to the horse races because she wants to show off her daughter. Hurstwood balks at the cost: one hundred and fifty dollars. After quarreling with Julia, he finally agrees to purchase one. However, his concession fails to heal the rift between them. Hurstwood notices that his family has stopped informing him of their activities. He begins to feel as though they are not giving him his due respect.
Meanwhile, Hurstwood and Carrie frequently exchange letters. He urges her to leave Drouet, but she says they must leave Chicago first because she does not want to get married as long as Drouet is around. Her mention of marriage shocks Hurstwood. He tells her that he will take her on a trip soon and that they will get married somewhere else. He is considering marrying her without divorcing Julia.