Stephen and Mr. Dedalus enter the Bank of Ireland, leaving the rest of the family waiting outside, so that Stephen can cash the check for thirty-three pounds he has received as a literary prize. Mr. Dedalus muses patriotically about the fact that the Bank of Ireland is housed in the former Irish Parliament building. Outside, the family discusses where to have dinner, and Stephen invites them to a fancy restaurant. This initiates a great spending spree in which Stephen regales his family members with costly gifts, treats, and loans.
Stephen's prize money is soon depleted, leaving him upset by his foolishness. He had hoped that spending the money would bring the family together and appease some of their animosities, but he realizes it has not worked—he feels as alienated from his family as ever. Stephen begins wandering the streets at night, tormented by sexual cravings. One night, a young prostitute dressed in pink accosts him. Stephen follows her to her room. He is reluctant to kiss her at first, but they eventually have sex. It is Stephen's first sexual experience.
In December, Stephen sits in his school classroom, daydreaming about the nice stew of mutton, potatoes, and carrots he hopes to have later. He imagines that his belly is urging him to stuff himself. Stephen's thoughts soon turn to the wandering he will embark on at night and the variety of prostitutes who will proposition him. He is unable to focus on the mathematical equation in his notebook, which seems to spread out before his eyes like a peacock's tail. He contemplates the universe, and imagines he hears a distant music in it. He is aware of a "cold lucid indifference" that grips him. Hearing a fellow student answer one of the teacher's questions stupidly, Stephen feels contempt for his classmates.
On his wall, Stephen has a scroll testifying to his leadership of a society devoted to the Virgin Mary. Mary fascinates him, and with pleasure he reads a Latin passage dedicated to her, reveling in its music. At first, Stephen does not see his veneration of Mary as being at odds with his sinful habit of visiting prostitutes, but he gradually becomes more worried by his sins of the flesh. He realizes that from the sin of lust, other sins such as gluttony and greed have emerged. The school rector announces a retreat in honor of the celebration of St. Francis Xavier, whom he praises as a great soldier of God. Stephen feels his soul wither at these words.
These sections explore the relationship between worldly pleasures and sin. The scene in which Stephen cashes his prize money is the first of several episodes in the novel that focus intensely on money and the thrill money evokes. The prize money Stephen wins seems strangely connected to his religion: the sum, thirty-three pounds, echoes Christ's age when he was crucified. Stephen confuses monetary and spiritual matters when he attempts to purchase familial harmony with money and gifts. In Christian theology, the sin of trying to exchange spiritual things for worldly ones is known as simony, a word that recalls the name of Stephen's father, Simon. This implies that such confusion of the material with the spiritual—with concepts such as faith and love—may be part of Simon's legacy to his son. Indeed, Stephen does have trouble seeing the incompatibility of some of his actions with his religious beliefs, venerating Mary even as he daydreams about visiting prostitutes. However, when Stephen says that his soul withers as he hears the rector praise St. Francis Xavier, it is clear that Stephen knows the church would view his acts as sinful.
Stephen's relationship with women becomes more complex in this section. He simultaneously displays a fervent devotion to the Virgin Mary and an obsession with visiting whores. In both cases, Stephen relates to women not as individuals but as representatives of a type. Both Mary and the prostitutes are described more as myths or dreams than as any element of everyday life. Stephen portrays Mary in a highly poetic and exotic manner, using evocative words such as "spikenard," "myrrh," and "rich garments" to describe her, and associating her with the morning star, bright and musical. However, when Stephen muses that the lips with which he reads a prayer to Mary are the same lips that have lewdly kissed a whore, we see that he has mysteriously linked the images of the whore and the Virgin in his mind as opposite visions of womanliness. Indeed, Stephen describes his encounter with the prostitute in terms similar to a prayer to Mary: when he kisses her, he "bow[s] his head" and "read[s] the meaning of her movements." When Stephen closes his eyes, "surrendering himself to her," this quiet submission mimics the Christian surrender to the Holy Spirit. Moreover, both the Virgin Mary and the prostitute represent a refuge from everyday strife, doubts, and alienation. Stephen attempts to flee mentally to the pure realm of the Virgin Mary when he is repelled by the stupidity of his classmates. Similarly, Stephen flees to the prostitute after reaching the dismal realization that his financial efforts have done nothing to allay the discord in his family. Like Mary, the prostitute offers him a chance to escape the discord around him in an almost religious way, if only momentarily.