The following version of this book was used to create the guide: Strout, Elizabeth. Olive, Again. Random House, 2019.

Olive, Again is divided into thirteen discontinuous yet interrelated chapters, each of which could function as a standalone short story. It is told in the third person, but each chapter focuses on one character, whose thoughts the narrator presents.

In the first chapter, “Arrested,” Jack Kennison, a former Harvard professor in his seventies, drove to Portland, an hour away, to buy whiskey in order to avoid Olive Kitteridge at the grocery store. The pair was beginning a romance, but Olive suddenly stopped answering his calls and emails. In Portland, he reflected on his past, particularly his relationship with his late wife, Betsy, with whom he had strained relations towards the end of her life after an affair with another professor became public. Jack called his daughter, Cassie, who lived in San Francisco and with whom he had not had a relationship since she came out as gay and he did not accept her. She rushed him off of the phone, not accepting his apology. At home, he emailed the man Betsy had dated before him to let him know Betsy had died, and he responded that he knew and that they had had an affair together.

Olive helped deliver a baby at a baby shower for a different woman. She called her son, Christopher, to tell him about it but he was uninterested. Lonely at home, she called Jack and went to his house, where she spent the night, albeit in a different room.

“Cleaning” tells the story of eighth-grader Kayley Callaghan who recently lost her father and lacked a significant relationship with her mother. While cleaning her English teacher’s house, one of a few houses she cleaned for pocket money, her English teacher’s husband found her touching her breasts and asked her to continue. She did and after cleaning she found an envelope of cash outside. This interaction repeated each week for several months until her English teacher let her go because her husband had developed dementia, and since she was retiring to take care of him she would not have time to clean herself. Kayley was heartbroken when the arrangement ended, and went to stand outside the man’s nursing home, wishing she could see him.

Christopher came to visit from New York with his second wife and their four children. The children were rude and dismissive of Olive, while her son became upset when he saw Olive had gotten rid of some of her former husband’s belongings. When Olive tells him that she was marrying Jack, Christopher grew angry and was then rude to Jack when he came to introduce himself. Christopher’s wife yelled at him for being rude, causing Olive to reflect on the fact that she had publicly yelled at her husband that way.

Olive ran into her former student, Cindy Coombs, at the grocery store and learned that she was very ill. Olive began to visit her frequently and discuss Cindy’s regrets and fears surrounding her illness, simultaneously considering her own past.

In “The Walk,” Denny Pelletier reflected on his life and what he considered might have been his negative influence on his children who, like him, married quite young. At the outset of the walk he felt that he, at age sixty-nine had little to look forward to in life. In the course of his walk he remembered an outwardly successful girl from his youth who had killed herself after finishing university as a result of sexual abuse from her father. He then came across a boy from his daughter’s class overdosing on a bench and called the police, saving his life. After reflecting on these two lives, he realized that he and his family were doing just fine, and that he had much to look forward to in life.

Jim Burgesses and his wife, Helen came from New York to visit Jim’s family in Crosby. Helen was left alone with the wife of Jim’s brother, who made little effort to get along with Helen. As a result, Helen got quite drunk and fell down the stairs, causing her sister-in-law to realize how cruel she had been.

Olive ran into another of her former students, who had recently become the Poet Laureate of the United States, at a diner. The two talked and Olive shared a great deal about her life. Months later, Olive learned via a magazine someone left in her mailbox, that the girl had written a poem about her, suggesting that Olive was lonely and terrified. After some reflection, Olive realized that the girl was right.

Lisa Macpherson came back to Crosby from New York to visit her parents who, in their 42 years of marriage had spent thirty-five years living in a house divided in half with duct tape and communicating. Upon arrival, she told them she had been in a documentary about her work as a dominatrix. Initially, this caused great conflict, but her parents eventually came around and in doing so healed their relationship.

One night, Olive and Jack were eating dinner in a nearby town when they saw the woman with whom Jack had had an affair at Harvard. Her coldness causes the two to fight on the way home and Jack reflected to himself that he missed his first wife.

Suzanne Larkin came back to Crosby after her father’s death in a house fire, and found her mom suffering from dementia. She met with her father’s lawyer Bernie Green who helped her process the information she learned while in town, including knowledge of her father’s affairs and a comment from her mother which suggested she had molested her son, who later became a murderer, as a child.

Olive had a heart attack and her son, Christopher, grew more supportive in response. Christopher helped her move into a nursing home, where she made a new friend with whom she quickly bonded over their life histories.