Stephen spends the summer at his family’s house in Blackrock, a suburb of Dublin. He spends most of his time with Uncle Charles (actually his great-uncle), who has a penchant for strong, ill-smelling tobacco and minor shoplifting (he lets Stephen grab handfuls of fruit from a local store). After running daily errands each morning, Stephen and Uncle Charles go to the park to meet Mike Flynn, a retired athletic trainer and a friend of Stephen’s father. Mike teaches Stephen running techniques and makes him do laps around the park. Stephen enjoys running, but feels put off by the aging trainer’s appearance. On the way home, he and Uncle Charles usually stop by the chapel to pray.
A significant aspect of Stephen’s maturation is his growing disenchantment with and even disgust for adult figures he had once revered. The priests at school suddenly seem spiritually flawed and physically repellent. Mike Flynn’s aged body also repels Stephen, and inspires a mixture of pity and contempt. At the same time, Stephen's new confidence and growing powers of scrutiny cost him a generalized warmth and kindness.
On Sundays, Stephen, his father, and Uncle Charles go for long walks around the neighborhood. Stephen listens eagerly as the men talk about politics and family, and looks forward to a time when he can truly take part in the world they describe. In the evenings he reads The Count of Monte Christo, imagining himself as the wiser, older count who eventually rebuffs his once-beloved lover, Mercedes.
Stephen feels that the world of adults is defined by various political and familial loyalties. He understands that such an adult world is his future but he can’t participate in it at all, for now. He feels much more connected to the imagined world of his novel.
Stephen and a boy named Aubrey Mills become friends and form an adventurers’ club; they explore and fight imaginary battles. Stephen decides to make his costume very simple, like Napoleon’s. Sometimes they go with the milkman to the cow fields in the summer and the cow yards in the fall – the latter sadden and disgust Stephen.
Just as he briefly identified with Daedalus, Stephen tries on the costume of Napoleon, the classic symbol of megalomania. Stephen begins to yearn for a certain kind of confidence and power associated with historical Great Men.
Aubrey goes to school in the fall, but Stephen does not return to Clongowes: his family has been experiencing financial troubles. He imagines living the pleasant life of the milkman, but his vague sense of ambition does not let him dwell on it. His ambition takes the form of a confused, gloomy restlessness. He wanders around his neighborhood, feeling acutely that he is separated in some way from everyone else, and dreams of finding in the world something that resembles his soul.
Stephen spends more time thinking, observing, and constructing ideas about the world; in a way, he builds his own, separate imaginary world from his observations and emotions. This imaginary world is partly wishful thinking: it is a more intense, more exalted, more orderly version of reality. The gap between imagination and the more disappointing reality pains Stephen.