At dinner at the house where she lives, Roberta is caught out in a lie about where she spent the weekend. She had said she was going to visit her sister, but two of the girls from her boarding house saw her with Clyde. Roberta is embarrassed that her friend Grace is there to hear this, and also annoyed about the way she is questioned by the other girls regarding how she spends her time. After dinner she quarrels with Grace and decides she must find new lodgings. She takes a room in a house owned by a Mrs. Gilpin. The room is set off from the main part of the house and allows her to come and go without passing through any other portion of the house. She knows that this will enable Clyde to secretly visit her, and she also knows that this is a potentially dangerous situation for her. But she takes the room anyway.
It is early October, about six weeks after Roberta takes the room. The weather is getting colder, and it will not long be possible for Clyde and Roberta to continue to meet each other and stay outside all the time. Clyde asks if it would be all right for him to come and see her at her home. Roberta refuses, saying it would not be right. Clyde gets angry, but Roberta still says she cannot do it. He walks off, leaving her. She is tempted to run after him, and she feels pain at his departure, but she restrains herself.
Roberta is troubled and does not know what to do to resolve the problem. She believes it would be wrong to invite Clyde into her room. But she is in love with him and also thinks that because of his social position he is a good marriage prospect. For his part, Clyde is unhappy and resentful. He feels that if he gets further involved with Roberta she may expect more of him than he is willing to give. He has no desire to marry her, since as a Griffith he thinks he can aspire to someone of higher status than she. Nonetheless, he is in love with her and desires her. At the factory he ignores Roberta until she sends him a note begging him to see her. She wants him to meet her on the street in the evening, and he conveys a message to her that he will.
Clyde and Roberta are unable to resist temptation, and he visits her many times secretly in her room, where they make love. They continue to meet, even though both regard it as sinful. Clyde’s self-confidence grows and Roberta feels that she is dependent on him. Clyde is devoted to her, and into early December they are very happy together. Clyde, however, is unable to forget his desire to enter the social world inhabited by the Griffiths, and rebels against the idea that Roberta, a factory girl, is all he can expect in life.
One November evening Clyde encounters Sondra Finchley by chance in the street. Sitting in her car, she at first mistakes him for his cousin Gilbert, whom she dislikes. But on recognizing Clyde, she invites him to get into her car and she will have her chauffeur take him wherever he wants to go. Clyde is overawed to be in her presence, and she is charmed by him and aware that he is admiring her. She expresses the hope that they may perhaps meet again, and Clyde eagerly expresses that hope, too.
Clyde longs to know the beautiful and well-connected Sondra better. He thinks she is perfect. That evening he does not want to see Roberta and makes an excuse not to do so. Meanwhile Sondra reflects on their meeting and decides she likes Clyde, mostly because he is not like Gilbert. She also thinks he is better looking than Gilbert. She decides to get to know Clyde just to irritate Gilbert, so that Gilbert might see that perhaps he has a social rival in Clyde. Sondra gets her friend Jill Trumbull to invite Clyde to a dinner dance. Clyde is thrilled, knowing that Sondra will be at the dance. That night, he does not want to see Roberta.
This is one of the fateful turning points in the novel. Clyde, as always a romantic, is swept away by his emotions. He is so taken with the possibility of striking up a friendship with a young woman he regards as a “goddess” that he almost overnight grows cold to Roberta. The lure of the social connections he desires, and thinks he deserves, is too much for him. He insists to himself that he has never promised to marry Roberta, unless under certain circumstances. He means if she were to become pregnant, although he seems confident this will not happen. In his heart he knows he has behaved dishonorably to Roberta, taking advantage of her innocence with no promise of any reward. For her part, Roberta believes that he will never leave her.
Dreiser believed that people’s fates were largely determined by factors such as heredity and environment, but he also made room for chance events that could alter a person’s course. One such chance event happens in this section: Clyde’s encounter with Sondra on the street in which each arouses the interest of the other. The meeting only happens because Sondra mistakes Clyde for his cousin. It is this meeting that sets in motion the chain of events that will lead to the tragedy.