The following version of this book was used to create the guide: Tyler, Anne. Redhead by the Side of the Road. Alfred A. Knopf, 2020.

Tyler's novel is divided into eight chapters. The action of the novel describes a week in the life of a 43-year-old-man, Micah Mortimer, who runs his own tech support company and also manages a tenement building. Each chapter describes a day during a single week in his life. The chapter structure follows this timeline, where chapter one falls on a Monday, and the last chapter falls on the following Monday. The novel is told from the point of view of a third-person semi-omniscient narrator who does not figure as character in the action of the novel. Following the time frame of the week, the events of the plot are told in linear chronological order. Scenes from the characters’ pasts are narrated whenever relevant to the present action. The novel is set in the city of Baltimore.

The novel begins with a portrait of Micah's life and daily routine. His life is described as never varying from his usual activities, which include running, housekeeping, responding to tech support calls, addressing building tenants' needs, and spending evenings with his girlfriend, Cass, who lives separately from him. However, over the course of the week described in the novel, the tidiness of his life is disrupted by the arrival at his doorstep of Brink Adams, a college freshman whose mother was once Micah's girlfriend. Brink has run away from college, and he seeks out Micah because he believes Micah to be his biological father.

The arrival of Brink upsets Cass, who believes that Micah invites Brink into his house only to create an excuse not to offer her a place to stay after she had expressed to Micah her concern over being evicted from her residence. Even though this was not Micah's reason for inviting Brink into his home, he nevertheless is insensitive to Cass' worries. The reader is lead to conclude that Micah is habitually insensitive to others' feelings, insofar as other people's feelings bring an unwanted element of chaos into the tidiness of his life.

This event precipitates Cass' decision to break up with Micah. When he calls her to invite her to a dinner at his sister's house, she tells him that they should stop seeing each other. The next day at his sister's house, he explains to his family that Cass has broken up with him. His adult siblings dredge up episodes from Micah's personal history in order to explain why he insists on such a rote and tidy way of life, and the narrator draws the connection between this history and its effect on Micah's love life. At this dinner, he also tells his family about Brink, and how he had kicked Brink out of his apartment when he refused to tell his mother, Lorna, where he was. His family questions him why he did not contact Lorna himself, or otherwise actively intervene in reuniting together Lorna with her son. When Micah returns home that evening he finds Lorna on the internet and sends her a message.

The next day Lorna shows up at Micah's residence. She tells Micah about Brink's situation prior to his leaving school. They also reminisce on their shared past, and Lorna asks about Micah's family. Around this time, Micah goes to return some personal belongings to Cass. When they meet, Micah desires a reconciliation of some kind, however his inability to properly emote prevents this from happening.

On a later day, Brink appears at Micah's residence. After he invites him inside, Brink tells Micah that he was suspended from school until he admitted to his parents that he cheated on an assignment and a meeting was held between Brink, his parents, and the dean. Micah then alerts Lorna that he has found Brink. After some time, Lorna and her husband, Roger, arrive. While Brink is speaking to Roger alone outside, Micah confides in Lorna about the failures of his love life. Lorna explains her side of the story as to why they broke up years ago. Micah interprets this as an accusation that it was his fault. Roger and Brink then reenter the house and Brink explains to his mother why he left school. His remorse is described as insincere.

The next day, Micah finds himself driving near the school where Cass teaches. He stops and goes to the school playground and asks the children where Cass is. Micah then trips on a sweater, and when Cass arrives on the scene she finds Micah with his knees muddied and scuffed. She takes Micah into her arms, and they walk together off of the playground. Micah feels optimistic that Cass will give him a second chance.