Olive Kitteridge is a collection of thirteen short stories, essentially a "novel in stories," linked by the character Olive Kitteridge. What makes Olive striking is the variation in her roles throughout the book. In some of the stories, Olive is the main character. In others, Olive is only a supporting figure, a foil, or nothing more than a name mentioned in passing conversation—a theme or trope that links these stories set in and around the small town of Crosby, Maine.
The first story, "Pharmacy," focuses on Olive's husband, Henry Kitteridge, as he looks back from retirement age at what may have been the happiest year of his life. That year, his assistant at the pharmacy retired, and a new woman came to work there, a shy, college-educated young woman named Denise Thibodeau. Henry becomes very fond of Denise and her husband, Henry, and they and Jerry McCarthy, who makes deliveries to the pharmacy, become a kind of surrogate family to Henry Kitteridge, replacing the distance and tension he feels with Olive and their son, Christopher. Then Henry Thibodeau goes hunting with his best friend, Tony Kuzio, who accidentally shoots and kills him. Henry Kitteridge steps in to become even more of a father to Denise, teaching her to drive and helping her get back on her feet. She does, and eventually marries Jerry.
The second story, "Incoming Tide," is also marked by reflection on the past. Kevin Coulson has returned to Crosby for the first time since he was thirteen. His father had moved the family away after Kevin's mother had killed herself. Kevin is sitting in his car by the marina, watching the activity on the water and in the marina diner, where Patty Howe, a friend of Kevin's when they were both children, is waitressing. Olive Kitteridge, who had been Kevin's seventh-grade teacher, sees him and gets in his car. They sit and talk about the time since they had seen each other last, and about the suicides in their families (Olive's father killed himself). As they talk, both think about other people in their lives who have mental illnesses: Olive's son, Christopher, who is depressed, and Kevin's ex-lover Clara, who cut herself. Suddenly Olive jumps out of the car, calling for Kevin to follow her. Patty Howe, depressed over being unable to have a baby, has jumped into the water, and Olive and Kevin keep her from drowning.
"The Piano Player"
Angela (Angie) O'Meara, the main character in "The Piano Player," has been playing piano four evenings a week in the Warehouse Bar & Grill for over twenty years. Angie loves playing piano—she taught herself, starting at four years old, and never had a lesson—but she gets stage fright every time she plays, and so comes to work somewhat drunk every evening. "The Piano Player" takes place one evening not long before Christmas. That night, Angie calls Malcolm Moody, the town selectman she has been having an affair with for twenty-two years, and breaks off their relationship. Then, she sees Simon, a former lover, who tells her an unpleasant story about Angie's mother approaching him sexually decades before. After she gets off work, Malcolm accosts her, insulting her as a "nut" and a "drunk."
"A Little Burst"
"A Little Burst" takes its title from one of Olive's beliefs about life: there are "big bursts" of energy (e.g., having kids) in life that are very important but somewhat dangerous, and there are "little bursts" (e.g., a waitress at a coffee shop recognizing you) that get you through the day. "A Little Burst" is set a few hours after one of the big bursts: Olive's son, Christopher, has just married a woman named Suzanne who is, like Christopher, a doctor. Olive is hiding upstairs in Christopher's house, which she and Henry built, taking refuge from the crowd at the reception. There Olive overhears people outside the house talking. Someone asks her new daughter-in-law what she thinks of her in-laws. Suzanne calls Henry "a doll," but judges Olive's clothes unkindly and says that Christopher had a hard life (with Olive as his mother). Olive is upset, and filled with intense memories of her years raising Christopher. She takes her small revenge on Suzanne—a "little burst"—by damaging a sweater and stealing a bra so that Suzanne will be hurt, confused, and frustrated later.
Harmon overhears a young couple on the street and finds them charming. The couple later gets into trouble with the law, and then breaks up. The girl, Nina White, ends up coming to Daisy Foster for emotional support. Harmon and Daisy are lovers, and when he comes over to visit Daisy one Sunday morning in November, he finds that Nina is there. They try to help Nina, first with being upset over the breakup, and then with her anorexia, as does Olive, who stops by Daisy's when soliciting for charity. However, they fail, and Nina dies of a heart attack. In the course of the story, Harmon realizes he is not just sleeping with Daisy: he loves her.
"A Different Road"
Olive and Henry Kitteridge go out to dinner one evening. After dinner, Olive desperately needs to go to the bathroom. They cannot find a place, so Henry stops at the hospital. When Olive asks to use the restroom, the doctors there insist on checking her health, especially for allergies to crab. Just after Olive has changed into a hospital...