Henry Kitteridge, husband of Olive Kitteridge, is a pharmacist. He hires a shop assistant, Denise Thibodeau. Denise is 22, plain and newly married for one year (to a man who is coincidentally also named Henry). Denise is pleasant and she brightens up Henry’s days. Jerry McCarthy is a delivery boy at the shop, and Denise encourages him to go back to school and improve his life.
One day, Denise’s husband is killed in a hunting accident. With her being widowed, Henry takes it upon himself to teach Denise things like how to drive or how to write a check. Henry even finds her a kitten to raise. However, Denise runs over it with her car in an accident a year later, and she is heartbroken. Henry, again, tries to comfort her. Henry considers leaving Olive, but then dismisses it as unthinkable.
Denise ends up marrying Jerry, who ends up being fairly successful. Henry recalls that her telling him about the proposal, and him telling her “Go.” Denise and Jerry move away, though Denise continues to send Henry notes on his birthday. When Denise writes one day saying how blessed she feels for her life, Henry feels a sense of loss. He realizes he secretly felt a connection to her all these years, though Denise truly moved on.
Kevin Coulson sits in his car near the marina, contemplating suicide. As a child, his mother committed suicide, and he was the one who found her body. He grew up in Crosby but they moved to New York after his mother’s death. He’s back to visit. Olive Kitteridge pulls up in her car as well and join him to talk to him. Olive asks how he’s doing and confides that her father committed suicide as well. Patty Howe, a waitress who used to know Kevin when they were kids, sees the two of them sitting outside. She goes into marina to clip a few lilies from a nearby patch.
Kevin thinks about Clara, his ex who left him. She was obsessive, unstable and cut herself. Kevin finds Olive’s voice comforting but also tries to hint to Olive for her to leave, but she persists in talking to him. Olive asks after his brother, a drug addict, and Kevin tells her about his father dying from liver cancer a year prior.
As they’re sitting in the car, Olive rushes out because she sees Patty has fallen in the water. Kevin dives in and is determined to save her. As she holds on to him, Kevin marvels at the beauty of her will to live.
The Piano Player
Angela O’Meara is in her fifties and plays piano at the local cocktail lounge. She’s a bit of a closed off person and keep people at a distance. She has played there for a long time, but still needs vodka to ward off her stage fright. Angela has been carrying on an affair with a married man, Malcolm Moody, for years. But this day, she sees Simon, an old flame, in the crowd and decides to cut things off with Malcolm. She calls him during intermission and ends things.
However, when Simon finally comes up to her, Angela senses an unfriendly demeanor. Simon insults her, and he tells her about her mother, a prostitute, propositioning him once. Angela realizes he’s an unhappy man who is unfulfilled in his career and unhappy in his marriage, and that he’s taking it out on her. Afterwards, Malcolm finds her and bitterly insults her as well.
Angela thinks about these unhappy people, but then thinks about the kind people in her life as well, such as Joe (the bartender), Walter (bar patron) or Henry Kitteridge (who came in that night). She decides to focus on the kind people in her life, and she decides that tomorrow she’ll open up to Joe about a personal issue (she recently found bruises on her mother who’s living at a nursing home).
A Little Burst
At 38, Christopher Kitteridge (son of Olive and Henry) gets married to a nice woman and gastroenterologist, Suzanne Bernstein, after only knowing her about six weeks. After the wedding at Suzanne and Christopher’s house, Olive wants to go home and worries about Christopher’s future happiness. She thinks about life and the fact that people need both big bursts (the weddings, the births, etc.) of happiness and little bursts of happiness (a smile, a wave, etc.) to be happy.
Olive overhears Suzanne talking to a friend privately about Christopher’s difficult childhood, and Olive feels indignant. (Suzanne also comment disparagingly about what Olive assumes to be her dress.) Olive thinks about how much she loves her son. She remembers not too long ago she took him to get medicine for his depression. Angrily, Olive goes to the closet and steals one of Suzanne’s sweaters, a pair of shoes and a bra. Olive contents herself with giving Suzanne this minor inconvenience of missing clothes — and gives herself a little burst of happiness — and leaves.
A young unmarried couple, Tim Burnham and Nina White, are outside a restaurant on the marina, waiting for a spot to open up. Harmon, who runs a hardware store, listens in as the young couple discuss smoking pot and going to a party later. Harmon has breakfast and brings doughnuts to Daisy Foster, a widow whose husband passed three years ago. Harmon and Daisy are having an affair, but a largely physical one. Harmon return to his wife, Bonnie, afterwards. Harmon and Bonnie’s sons (Derrick and Kevin) are grown, and they no longer have sex.
Later, Harmon reads in the newspaper that the couple was arrested after the police broke up a party at their place and found marijuana. Harmon and Daisy start talking more instead of having sex, and they chat about the young couple. Harmon hears from Kathleen Burnham, Tim’s aunt, that the girl Nina is anorexic.
One day, Daisy tells Harmon that Nina is staying with her because Nina and Tim broke up. Nina had turned to Daisy for help. Harmon and Daisy try to encourage Daisy to eat. Olive shows up to pick up a check from Daisy and feels heartbroken at the sight of Nina, who clearly needs to eat. Olive is determined to help and eventually they are able to call Nina’s mother and get Nina admitted into a hospital.
Harmon and Daisy continue following Nina’s progress and cheering her on, all the while Harmon grows distant from Bonnie. However, Nina ends up dying. The whole interlude makes Harmon realize that he’s in love with Daisy. The chapter ends with Harmon not knowing comes next, whether he’s going to leave his marriage or get kicked out by Bonnie or what.
A Different Road
Olive reflects on something that happened one night, when Olive is 69 and Henry is 68. Christopher has recently moved to California with his new wife. Olive and Henry had had dinner with their friends Bill and Bunny Newton. Afterwards, Olive needed to go to the bathroom, so they stopped at the hospital to use their restroom. However, at the hospital they keep asking her questions about her health when she says she has diarrhea. As she’s waiting on the doctor, two masked men (Pig-Face and Blue-Mask) with guns show up looking for drugs. They force Olive and Henry into the hospital bathroom, where they are held hostage.
As they are sat there, Olive and Henry erupt into an argument when a nurse starts to pray. Olive criticizes his mother (Pauline) her brand of intolerant, judgmental Christianity. Olive reminds Henry of how Pauline referred to Olive’s father’s suicide as a sin. Olive also says that perhaps the reason Christopher moved away was because he married a Jewish woman and was worried Henry would be judgmental. Henry then counters, saying that Christopher left because Olive has always suffocated him.
After the ordeal is over, Olive realizes their relationship will always be a little different, not because of being held hostage, but because of what they said to each other that night.
Bob and Jane Houlton (75 and 72, respectively), an older married couple, are on their way to a church concert. They talk their friends Alan and Donna Granger. They also see the Kitteridges, and Jane comments that Henry loves Olive, which is why he can stand her. On the way home, Jane asks Bob about the Grangers’ comment that they ran into him at the airport in Miami, which he never told her about. Bob eventually admits that four years ago he went to Miami to see a former flame (presumably, a mistress) who had gotten breast cancer.
Jane is upset. However, when they go to sleep and he has a bad dream, she still comforts him. She figures they’re all each other has left.
Olive and Henry’s son, Christopher, announces that he’s getting a divorce roughly a year after the marriage, but he intends to stay in California. (Olive recalls a conversation about tulips, and how their ability to bloom lies in its bulb. It’s a reminder that power ultimately lies from within.) Henry soon suffers a stroke. He’s alive, but not responsive and paralyzed so he’s moved to a nursing home. In their house alone, Olive feels lonely.
Olive notices a kind note from Louise Larkin one day, noting what a nice man Henry was. Roger and Louise Larkin are a couple that lives in town, but are now shut-ins that are rarely spotted following an unfortunate incident (it’s implied that their son murdered a woman by stabbing her to death). It prompts her to visit the Larkins, though the visit is creepy and tense. Olive wants to tell someone about it, so she goes to see Henry.
Olive realizes on some level that she only went to see Louise, who she never really liked, in order to make herself feel better about her own life. Olive desire for schadenfreude was called out by Louise, but Olive now recognizes it was wrong for her to desire it. The story ends with Olive deciding whether or not to plant tulips again.
Basket of Trips
Marlene Bonney’s husband Ed, the town grocer, has passed away from an illness. The community has gathered for the funeral. Olive rides with Molly Collins to help set up sandwiches for the reception afterwards because she knows Henry would have done it if he were still able. Marlene and Ed were former students of Olive. Seeing Marlene surrounded by family, it dawns on Olive that the real reason she came was in the hope that someone else’s sorrow would life her own. But it’s now really working. She wants to leave, but her car is boxed in.
Kerry Monroe, Marlene’s troubled cousin, gets drunk at the reception and Marlene puts her to bed. Marlene confides to Olive that earlier in the day, Kerry admitted to cheating with Ed once many years ago. Marlene also admits to feeling embarrassed about all the plans she and Ed made, their “basket of trips,” even while his health was declining.
Olive wants to comfort Marlene and has some idea of what to say or do, but she’s not in the habit of doing those things and doesn’t quite know how to do it, and so she looks out the window instead.
Ship in a Bottle
Anita Harwood tries to comfort her daughter Julie Harwood who is 21 and has just been left on her wedding day by her fiancee, Bruce. Bruce wanted to move in together, but Anita had insisted they get married first. Julie’s stepfather Jim, who is kind but a recovering alcoholic as well as the janitor at the local school, and is building a boat in their garage, but he has realized it may end up being too large to get out.
When Bruce comes by to talk, Anita shoots at him to scare him off. He’s okay, but when the dust settles, Julie talks to Winnie, 11, her little sister. She tells her about how their life is strange because their mother insists on staying in this ramshackle house, and that their mother isn’t normal. Julie tells Winnie about the advice her teacher Mrs. Kitteridge had given her class: “Don’t be scared of your hunger.”
Julie decides to run away to be with Bruce.
Olive Kitteridge, at 72, goes on a trip to New York to see Christopher. Christopher has now remarried to a woman named Ann, and now has two stepchildren. Ann is pregnant and Christopher needs help, so he asks Olive to please come to stay. In New York, the house is chatic, but Ann is open and friendly.
Upstairs, a family with the surname O’Casey is subletting the unit. Olive wonders if they are related to Jim O’Casey, a former colleague of hers that Olive had fallen for, but never physically cheated with. Like Olive, Jim had been married with children. However, Jim was killed in a car accident before anything transpired between them, and Olive had grieved for him. Olive thinks about how kind and Henry was, but also about the deep loneliness she had felt at times.
The visit is going well, and Olive is feeling happy until she notices that she’s dripped sauce over herself and no one told her. She thinks to herself that they must think of her as a useless old woman and is suddenly irritable and determined to leave. Christopher tries to coax Olive into telling him what’s going on, but Olive refuses. Christopher tells Olive that her suddenly changing moods were difficult for him growing up, but Olive refuses to engage. Christopher then simply helps her leave, saying he’s not going to let her make him feel bad about it any more.
At the airport, Olive considers calling Christopher to patch things up, but then changes her mind. When the airport officials ask her to take off her shoes, she refuses and the airport security is called over.
Rebecca Brown was raised by her father, a Congregation minister, because her mother ran off to be an actress. (She’s also Olive’s former student.) Her husband is a bit patronizing and condescending, in a passive aggressive way.Her controlling and cold father has recently passed away, and she starts thinking somewhat deviant thoughts, like things about inappropriate sex or pyromania. She also starts having kleptomaniac tendencies, like stealing a magazine and vase from the doctor’s waiting room. She goes to a doctor because she feels unwell, but he’s dismissive of her concerns. She only feels better when she steals something from him.
At the end of the story, Rebecca heads out of the house at night, calculating that the doctor’s office is a 30 minute walk away. Before doing so, she rips up her postcards from her mother and puts it in a bag, along with a magazine she stole and a shirt that reminds her of an ex. She also takes along the barbecue starter supplies and two cigarette lighters. (I think the story is implying that she is going to take these things, burn them and start a fire at the doctor’s office.)
The Kennisons are a couple who moved to Crosby for retirement. Olive is weary of retirees and summer people, who she feels have too much money and seem entitled. Henry has now passed away, and Olive hopes her own death will be quick. Olive thinks that Bunny, even though her husband has annoyed her their whole life, has won the lottery simply because he’s still alive.
Olive is at the beach one day and sees that Jack Kennison has fallen and needs help. She waits with Jack for help, and he confides that his wife died in December. After Jack is admitted to the hospital, Olives goes to check up on him. Soon, they make plans for dinner together, and eventually he kisses her.
Jack admits that his daughter hates him, because she is a lesbian and he disapproves. Olive admits to him that Christopher hates her too and it is probably her fault, something that she’s never been able to admit to Christopher himself. As Olive reflects on her feelings for Jack, she finds a renewed will to live.