Stephen is spending the summer at Blackrock, a suburb south of Dublin where the family had moved. He spends a lot of time with Uncle Charles, accompanying him on many errands. He runs in the park under the tuition of a coach, Mike Flynn, an old friend of Stephen's father. On their way home they would often visit the chapel, where Charles would pray. On Sundays, Stephen, his father and Charles take long walks. Stephen has the evenings to himself, during which he reads Alexandre Dumas' adventure novel, The Count of Monte Cristo, which stirs his imagination. He befriends a boy named Aubrey Mills and together they found a gang which gets up to some mild mischief in the neighborhood.
Stephen does not return to Clongowes in the fall, and he knows this is connected with his father's declining fortunes. The family moves from the comfort of Blackrock to another house that feels cheerless to Stephen. He has more time to himself, and wanders down to the docks and quays. He visits relatives with his mother, but he feels angry at the change of family circumstances, which has re-shaped his world. At his aunt's house, he encounters a girl called Emma, and meets her again at a children's party. He is entranced by her in a romantic way. They return home on the same tram, and the next day he writes a poem to her.
Stephen's father arranges for him to attend Belvedere College in north Dublin, another Jesuit school. At the end of his second year at Belvedere, he appears in a school play. During the gymnastic performance that precedes the play, Stephen wanders outside, where he meets a friend, Vincent Heron, and another boy called Wallis. The boys tease Stephen about the presence of Emma at the theater. It appears that Stephen has not seen her for two years, but he has thought about her a lot. Heron's insistence that he admit the presence of his imagined sweetheart leads Stephen to recall some events from the past when he was also pressured by others to admit to something. He remembers how in his first term Mr. Tate, the English teacher, accused him of writing a sentence in an essay that contravened the Jesuit interpretation of truth. Mr. Tate called it heresy, and Stephen was forced to amend his statement. A few nights later he had got into an argument with three of his classmates about their favorite writers. Stephen's choice of Lord Byron arouses the derision of the other boys. They grab him and beat him, trying to make him admit that Byron was not a good poet. After this humiliation he returns to the theater and acts his part in the play. He emerges afterwards in an excited state, and rushes past his father and other people he knows. He walks fast without even knowing where he is going, until finally he calms down and walks back.
In the next incident, Stephen travels by train with his father to Cork, where Mr. Dedalus had lived in his youth. They are going to Cork because Stephen's father's property is to be sold by auction. They stay at the Victoria Hotel, and visit Queen's College, where Simon Dedalus inquires after his old friends, only to find that many are dead. He searches for his own desk, in which he carved his initials. Stephen is restless and bored by the visit. His father tells him stories he has heard before and gives him advice, telling him always to mix with gentlemen. Meanwhile, Stephen is living a vivid imaginative life that makes it hard for him to relate to the real world. His memory of his childhood is fading. In the evening, after the property is sold, he and his father go from bar to bar, meeting and chatting with all Simon's old friends. They drink to the memories of the past. Stephen feels separate from it all. He feels he is merely drifting through life.
At Belvedere, Stephen wins some academic prizes. He buys gifts for his family and friends and lends out money. He tries to draw up some rules of life for himself, but when the money runs out, all his plans collapse. He feels isolated from his family, and that his life is a tissue of falsehood. He takes once again to wandering around the streets alone in the evening. He finds himself in a squalid area of the city, where the brothels are, and he has his first sexual experience with one of the prostitutes.
Several of the main themes of the novel appear in this chapter. Stephen emerges as an earnest young man, in some ways a model student at school, and certainly academically gifted. But there are tremendous forces building up inside him, for romance, sex, artistic creation and independence from the expectations of others. As yet, he does not know how to deal with all of them.
There are two opposite images of women presented in this chapter. Emma is the girl who inspires his mystical daydreams although she never appears directly in the novel. She is seen solely through Stephen's imagination. As an ideal feminine image, Emma is like the figure of Mercedes, the long-suffering love of the hero Dantes in The Count of Monte Cristo, who also becomes rooted in Stephen's imaginative life. On the other hand, there is the unnamed prostitute with whom Stephen has his first experience of sex. If Emma and Mercedes represent the ideal, the prostitute is an embodiment of a real, flesh-and-blood woman, and Stephen's sexual adventure with her (and with others in the next chapter), will cause him great feelings of guilt.
Like many a teenage boy, Stephen is not sure of what direction he is to take in life. His father and his masters at school urge him to become a gentleman and a good Catholic. At Belvedere, he is exposed to the cultural atmosphere of the times, in which a number of organizations were being founded with the intention of reviving the Irish language and Irish tradition. Some people tell him he should become part of this revival. Others advise him to work hard to restore his father's worldly fortunes. But all those voices ring hollow for Stephen. They are all part of the pressure to conform to the expectations of others, a theme which is also noticeable in the episodes where others try to force him to admit to something that he does not believe in.