In May, Olive Kitteridge travels to New York for the first time to visit Christopher, who has remarried. Ann, his new wife, has two children from prior relationships and is pregnant with Christopher’s child; Olive has been “summoned to help” (201). Everyone in Crosby told her that the trip would be good for her. When she arrives at the airport, Christopher seems furious because he has had to wait, partly because Olive refuses to get a cellphone. In the car, Christopher finally asks after Henry and instructs Olive not to refer to his son, Theodore, as “Teddy.”

At the house, the children are playing in the cramped concrete garden to the rear. Olive meets Ann for the first time; Ann has a “stomach huge and hard” (205) and embraces Olive. Theodore cries a lot, and the baby, Annabelle, splashes water in a small plastic pool. From above comes the sound of a parrot reciting Christian exclamations—the fundamentalist Christian renting the apartment owns the parrot and has trained it to respond that way whenever someone swears.

The family eats quickly, but Olive is not hungry. Afterward, Olive lays down in the basement and calls the nursing home. Asking to speak to her husband, she explains everything to a nonresponsive Henry. Later, she steps out to find Ann smoking a cigarette and drinking a beer despite being pregnant; Olive struggles to make sense of this woman, who in several ways is a reflection of herself. They sit together while Christopher reads to Theodore, and then, as Christopher joins them in the garden, Ann departs, leaving Olive and Christopher in silence. Eventually, they make small talk about the tenant. His name is O’Casey—just like someone Olive once knew.

Olive remembers Jim O’Casey from Crosby; they met at a town meeting. She remembers the way he looked at her. By the next year, they worked together at the school. Every morning, Jim drove both Olive and Christopher to the school. Over lunch, he would ask her whether she would leave Henry to be with him. Olive, emphatically, would say yes. However, they “never kissed, nor even touched” (213). Then, the phone call came in the night: Jim had driven off the road and into a tree. He died, and Olive was forced to cope with her profound grief in private. Christopher jokes about his tenant being related to Jim O’Casey and admits that he never liked Jim. Nonetheless, Olive sleeps well that night.

The next morning, Theodore cries about juice boxes and refuses to be taken to school by Olive, who takes the family dog to the park instead. There, she meets a man who she assumes is one of Christopher’s friends. Olive feels the man is being vulgar, talking about Christopher’s private business. The man’s dog eats an old dead pigeon, causing a commotion, and Olive leaves. Spotting a parrot on the man’s shoulder, though, she realizes on the way home that the man is the religious tenant from upstairs. She believes that Christopher should not be living in the city because “he was not a fighter” (218).

At home, she discusses the tenant with Christopher, who reveals to her that Ann’s mother has an alcohol addiction. Olive asks her son whether he worries about another terrorist attack. Christopher says no, but he shares his racist beliefs about a local Pakistani shopkeeper, who has since returned to Pakistan.

The days pass. Despite the strangeness, Olive appreciates being with her son. On the third day, she watches the baby. For a moment, Olive forgets about Annabelle; when she rushes back, her attempts to help result in the baby crying. Ann arrives, laughing and offering assistance, and reveals that it is her and Christopher’s wedding anniversary. Olive refrains from complaining about no one telling her about the wedding and congratulates Ann. The couple met in a “singles group for divorced people” (222), Ann reveals, and they liked the group so much that when the therapist moved to New York, Christopher and Ann followed. Olive decides to “accept all this” (223) and, later, phones Henry and tells him everything.

Olive joins the family for ice cream. She and Christopher walk home side by side and argue about what Henry would have ordered. When they arrive home, though, Olive sees that she has spilled ice cream on her top, and no one mentioned it. She is repulsed, fearing that she has become pathetic.

The next morning, Olive announces that she is returning home. She tries to keep her anger in check, her anxiety mounting as she thinks that Christopher has certainly talked about her with his therapist. Christopher loses his patience and simply offers to call a car service for his mother. She accuses him of kicking her out; Christopher points out that “you say you want to leave, then accuse me of kicking you out” (229). Christopher then calms himself and begins to share what he seems to have learned in therapy. Olive can make people feel terrible, he explains, and she inflicted this on his father in particular. Ann tries to bring Christopher’s accusation to a halt, but he shakes his head; Olive starts to cry. She shouts at Christopher with “more and more fury” (230), until she is hardly aware of what she is saying. Christopher remains calm throughout. The car service arrives.

At the airport, Olive has to wait in a long line. As she waits, Christopher’s accusations filter through her mind. She was the scariest teacher in school, he told her, and today, a social worker would be called on her “if a kid showed up that way” (232). Olive, still emotionally raw, refuses to take off her shoes for the security checks, upset at the thought of exposing her “shredded panty hose” (232). Security comes and leads Olive away. She goes willingly.

Rebecca Brown is not “the type of person who stole things” (233). However, charmed by a story in a magazine, she took the magazine with her from a doctor’s office. In the back of the magazine, she finds an advertisement for a shirt and resolves to buy it for David, her current boyfriend. She spends a long time talking to the saleswoman who takes her order for the shirt on the phone, her tendency to talk too much on display.

Rebecca comes “from a line of Congregational ministers” (237). Her mother left to become an actress in California when Rebecca was young; her father raised her. Occasionally, her mother sent postcards; one explained that she had joined the Church of Scientology. Though Rebecca wrote to her mother often, she never received a reply. Growing up, Rebecca first studied Scientology. Then, as her wish for her mother diminished, she studied books “about being a minister’s wife” (238), following all the advice she finds. When she left for college, Rebecca worried about her father and told people that her mother was dead. During her father’s funeral, she begins to have “thoughts she knew couldn’t be natural” (239). When she prays, she insults her mother and apologizes to her father.

Rebecca shows David a job ad for a dental assistant; she has struggled to find work. David tries to make her feel better, giving her advice about how to interview. After they have sex, as usual, David falls asleep while Rebecca lays awake. On this occasion, she gets out of bed and goes to the kitchen to listen to the noise from outside. In the morning, David flexes and admires his muscles; Rebecca recalls that vanity is a sin. She remembers how her math teacher, Mrs. Kitteridge, had offered to talk “about anything” (242) with her, but Rebecca had not taken her teacher up on the offer.

Even though it was only Rebecca and her father, her father never allowed talking at the dinner table. Rebecca now has an almost uncontrollable urge to talk constantly. She phones and tries to change the shirt size, but it is too late, as the shirt has already been shipped. She talks to the same woman on the phone and discusses her need to find a job.

In college, Rebecca dated a pianist named Jace. She fell in love with him, but he broke up with her; around the same time, her father first told her about his heart condition.

Rebecca does not get the job as the dental assistant, thinking that she “probably talked too much” (246) in the interview. Eventually, she gets a job “typing traffic reports for a fat man who scowled and never said please” (246). After a few weeks, she becomes so bored with it she thinks she will quit. The shirt arrives: It is beautiful, but it is a shirt Jace would wear, not David, so she returns it. In the doctor’s office the next day, she searches “for something to steal” (247). She complains to the doctor about her stomach hurting, but he seems irritated with her. On the way out, Rebecca steals a vase from the waiting room.

Rebecca and David sit at home, watching television and talking about shoplifting when they were children. Rebecca never did—not because she thought it was wrong, but because she worried that someone would catch her. Reflecting, she becomes concerned that all the butter-soaked food she cooked her father may have caused his heart problems: “I bet legally that makes me some kind of criminal” (249), she says. David, only half-listening, tells her not to worry.

Beneath her window, Rebecca sees police cars gather. The cops arrest a man. The cars leave, and the kitchen is dark once again. She takes postcards from her mother, the magazine she stole, and the shirt she ordered for David and places them in a bag. She exits the house with two cigarette lighters, repeating the Miranda warning to herself as a mantra, thinking that “it would be worth the arrest if they put it like that” (250).

Olive Kitteridge almost backs her car into Jack Kennison in the library parking lot. He is “a tall man with a big belly, slouching shoulders, and—in her mind—a kind of arrogant furtiveness in the way he held his head thrust forward and didn’t look at people” (251). Jack attended Harvard and “let everyone know” (251), which always disgusted Henry. With his wife, Jack retires in Crosby. Jack’s daughter is gay, and Jack disapproves; Henry condemns this attitude, though Olive notes that Henry develops paralysis before Christopher remarries and dies before Christopher’s baby is born. This timing, Olive believes, means that Henry “had never been tested” (252).

Now alone, Olive does the same thing every day. She goes to Dunkin’ Donuts early and walks six miles along the river: “Let it be quick” (253), she thinks, as she considers her own mortality. One day, she finds Jack Kennison collapsed on the path; concerned, she rouses him. She offers to fetch help, but he asks her not to leave him alone. When Olive insists that he see a doctor, Jack says that he does not care if he dies. Olive helps him to his feet; Jack explains that he fainted while sitting on the bench. They sit for a while on the bench together, and Olive notices that Jack is crying. He explains that his wife died in December. Olive tells him, “Then, you’re in hell” (255)—he agrees.

Olive goes to the doctor with Jack and sits in the waiting room feeling “perfectly comfortable” (255). She reads a magazine but cannot stand to look at pictures of George W. Bush. After, she drives Jack back to his car and follows him home. He invites her in for lunch, but she refuses and leaves, later telling a friend that she plans to call Jack to check up on him. Their conversation is brief.

A week later, Olive has come to realize how invigorated she felt during her time with Jack. Everything she has tried since Henry died has been a failure. One morning, while walking, she sees Jack again. They briefly speak, and though Olive continues her walk alone, she thinks of Jack. When she gets home, she telephones him and invites him for lunch. He proposes dinner instead, and Olive accepts.

Olive bristles at her friend’s teasing (“Olive, you’ve got a date” [259]), but Olive’s mood nonetheless continues to improve. Olive invites Christopher and his baby to visit in the summer, and while they talk, Olive tells Christopher about her dinner plans with Jack. When Olive reports her friend’s teasing, her son says to think of the dinner as “volunteer work or something” (260). Olive agrees.

Olive meets Jack at the Painted Rudder; she is not impressed by his drink order (vodka and tonic), but talking with him is “kind of nice” (260). They meet for lunch the next week, and after, she invites him to her house.

The couple spends increasingly more time together. Jack kisses Olive on the cheek and then even on the lips, but Olive does not tell anyone, as it’s nobody else’s business. While picturing Jack embracing her, she also criticizes Jack for being “afraid to be alone” (262). Bad weather keeps Olive in the house, and she does not speak to Jack for five days. She talks with Christopher, who asks her about her date; Olive calls Jack a nitwit and refuses to admit that it was a date. Christopher has to go, but then, “like a rainbow” (263), Jack calls. They arrange to meet the next day.

As Olive and Jack walk together, Olive agrees to “rest whenever you want to rest” (263). They begin to talk about Jack’s daughter and her “alternative lifestyle” (264). Olive is adamant that she would not mind if her son was gay, but Jack argues that she is being sentimental. As the conversation shifts into politics, Olive begins to fume about the fact that “we have a cowboy for a president” (265). When Olive realizes Jack voted for the “cowboy-president,” reacting with horror to the news that he is Republican, Jack jokes that she is prejudiced against “white men with money” (266). Olive storms off.

Later, when Olive tells her friend about Jack’s politics, her friend merely laughs. Olive tells Christopher, too, who at least agrees that it’s “gross.” However, as Christopher starts to hint again at Olive’s problematic behavior, the call acrimoniously ends as Olive hangs up.

For two weeks, Jack doesn’t call. Olive stops speaking to people. Then, after waking alone in the middle of the night, Olive caves and sends Jack an email, asking bluntly whether his daughter hates him: “Yes,” he responds. Two days later, Olive emails back that her son hates her, too. They bond over their shared pain. Olive goes to walk the dog and, when she returns, there is another message from Jack, this time inviting her over to his house.

Olive goes. There is no answer when she knocks, but she enters anyway. Jack invites her to lay beside him on the bed, and he admits that he is scared. Olive halts herself before she admonishes him. Instead, she sits down beside him and looks into his eyes, seeing in them “the vulnerability, the invitation, the fear” (269). Feeling his heartbeat in his chest, she feels desire. She remembers Henry with some regret. However, as she closes her eyes, the waves of gratitude and regret washing over her, Olive gains a moment of apparent peace: “It baffled her, the world. She did not want to leave it yet” (270).