Frank’s class at school is going on a cycling trip to Killaloe in three weeks, and he carefully plots how best to approach Laman about lending him his bicycle to participate. He chooses his moment and joyfully agrees to earn the privilege by cleaning the chamber pot that is otherwise his mother’s responsibility to empty daily. He happily continues visiting the library and is doing well in school. His teacher Mr. O’Halloran even speaks to Angela about the importance of Frank continuing his studies rather than falling into the “messenger boy trap.” He suggests they visit the Christian Brothers and ask about a place for secondary school, but Brother Murray closes the door in their faces, declaring there’s no room. Angela reminds Frank that a similar incident occurred when he and his father went to inquire about becoming an altar boy, but Frank replies he doesn’t care, he wants to work. Even before his fourteenth birthday, Frank applies for the telegram delivery boy job. He flirts with the idea of becoming a missionary but the family doctor refuses to help with the application and sends him home, where his mother has taken to joining Laman Griffin in the loft, sometimes all night. Frank is repulsed to understand there’s “the excitement” up there. One day just before the trip, he makes the mistake of forgetting to empty the chamber pot. Laman declares the bargain is off and refuses to lend him the bicycle, physically assaulting the boy as he yells and screams while Angela does nothing. Frank is so upset he leaves the house, plotting his revenge. He dreams of going to America to tell Joe Louis about his troubles, but walks to his uncle Pat “Ab” Sheehan’s where he is permitted to lick the grease from the newspaper that once held fish and chips.
Frank stays with Pat and steals apples so he can refuse the food his mother sends with his brothers. He keeps going to the library but one day reading about virgin martyrs he comes across the word “turgid” and is caught looking it up. Disgraced, he concentrates on preparing for his first day of work, and decides to wash his clothes. He puts on a dress of his grandmother’s while his clothes dry, and is found that way when Uncle Pat comes home stumbling drunk with Aunt Aggie and Pa Keating because he fell down outside the pub. Even worse, they send Frank outside to fill the kettle where he is seen by Kathleen Purcell next door, who breaks into peals of laughter. Aggie questions his presence in the house, and Frank solemnly replies he intends to move his family to a better place as soon as he starts his job tomorrow.
Aggie intercepts Frank on his way to the post office the next morning, and tells him to let them know he’ll be an hour late. They respond by telling him his job doesn’t start until Monday anyway, and it’s only Thursday. Aggie surprisingly takes him shopping for proper clothes, mainly to prevent disgracing the family by reporting for work dressed in rags. The next week, Frank arrives proudly for work in his new clothes. His first telegram is addressed to Mrs. Clohessy, his old friend Paddy’s mother, and upon arrival there, Frank learns that both father and son have gone to England. She tips him generously, and at the end of the week Frank is rewarded with a whole pound in wages, which he spends treating his brother Michael to a night out. Despite the threat of losing his job for cashing a check for a customer, Frank sympathizes with the ill and elderly clients who cannot leave their homes, and does them such favors on the sly. He soon has his first order for the Carmody family, who are well-known for giving the biggest tips in Limerick. Frank is so excited anticipating the tip that he skids on his bike and arrives at the door bleeding. Seventeen-year-old and red-headed Theresa, who is suffering from the dreaded and unacknowledged tuberculosis, opens the door and insists on cleaning him up. He lets her dry his pants and they lose their virginity on her green sofa. They continue seeing each other for weeks, until one day Theresa’s mother answers the door and says only that her daughter is in the hospital, avoiding the shame associated with the sanitarium. Within the week, their house has the black wreath signifying death on the door. Frank is devastated to think he is responsible for Theresa being sent to hell for what happened between them. He observes the funeral from a distance and grieves for her premature death, a heaviness in his heart that can only be love.
Frank’s excitement about the cycling trip reminds the reader of the passions of an adolescent boy, and Laman’s betrayal of his promise to lend him the bicycle confirms he is a despicable character. Frank is outraged both at the personal offense of renegging on an important promise, and is further demeaned by Laman’s physical mistreatment of both him and his mother. Angela has begun sleeping with Laman to guarantee keeping a roof over her sons’ heads, but Frank is too disgusted by the grunting he overhears to sympathize with any of the reasons his mother may have resorted to nearly prostituting herself. He leaves when she sleeps with Laman even after he has beaten her oldest son, unable to forgive their sins and uncomfortable with his own increasingly sexual thoughts. Frank feels guilty about masturbating, which he learns from the priests causes the Virgin Mary to weep, and is conflicted about obeying his natural instincts and trying to be good. His relationship with Theresa perfectly illustrates these new and complex feelings, for he truly feels tenderly towards the sick girl and misses her deeply, but also thinks of their activities as somehow dirty and worries that she will be condemned to hell on account of his inability to control himself as the church suggests good Catholics should.