Jack Kennison drives to Portland, Maine to buy groceries in order to avoid running into Olive Kitteridge in their town Crosby. He stops at a bar, and he thinks about how he misses Olive. They had spent time together and kissed, but then she never called him again. That was three weeks ago.
He thinks about his late wife, Betty, who died seven months ago and about his affair with Elaine Croft. Jack had taught at Harvard, but Elaine had later filed a sexual harassment lawsuit against Jack, citing that as the reason she never got tenure. As a result, Jack had retired.
On the way back from Portland, Jack gets ticketed for speeding and his vehicle inspection is overdue. They breathalyze him, but he’s just under the legal limit. When he gets home, he looks up a man Betty once loved in her youth, Tom Groger, and informs him of Betty’s passing. Tom responds, admitting to a dalliance with Betty at one point. He’s angry, but ends up just writing a sincere note to Olive saying he’d like to see her again, but is unsure whether to send it.
Olive spots Jack Kennison who she’d spent some time with a month ago and never heard from again. Two days prior, Olive ends up at a baby shower that ended with her delivering a baby. She tells her son Christopher about it, though his wife has recently suffered a miscarriage. Olive finally calls Jack, who invites him to come over.
Jack asks why he never returned his messages, and Olive tells him she doesn’t use her answering machine. Olive sleeps over at a guest room at his place.
Kayley Callaghan is a 8th grader in Crosby, living with her widowed mother, since her father passed away from an illness two years ago. Her older sisters all have their own families and no longer live at home. They have a piano at home, but Kayley rarely has motivation to practice. Her mother is generally stressed out and distracted and does not pay much attention to Kayley.
Kayley cleans Bertha Babcock’s house for extra money, and one day her English teacher, Mrs. Ringrose, asks her to clean for her as well. Sometimes she goes to visit Miss Minnie, who she had really liked and cleaned for until Miss Minnie had a stroke.
When the house is empty, Kayley ends up touching herself sexually while she is in the Ringrose’s home. Mr. Ringrose arrives at home and sees her. He leaves her extra money. The next time she is there, he’s home and nods at her. She touches herself again with him watching and he leaves her extra money again. Kayley is excited about all of it and starts practicing piano with renewed energy. This continues for months.
One day, Mrs. Ringrose abruptly fires Kayley, citing health issues at home. Kayley feels bereft and quits her cleaning job at Bertha’s house. When she gets home, her mother has discovered some of the money, is furious that she’s quit that job and slaps Kayley. Kayley’s sister Brenda comes home and explains that their mother has been very depressed since their father died.
Kayley hides the extra money in the piano, but one day her mother sells off the piano, saying that Kayley never practices anymore. Kayley runs into Olive Kitteridge who tells her that Mr. Ringrose has lost his mental facilities and is being sent to a nursing home.
Christopher and Ann are coming in for a visit. The last time she saw him was three years ago, and the visit had gone poorly.
They come in with all their kids, and Olive is happy because Christopher is talking to her. She hasn’t told Christopher about Jack yet, though so when he asks about the car she’s driving (which is Jack’s), she lies and says she bought it. They decide to take the kids to see the coast, and on the way Ann confides in Olive that her mother died right before her miscarriage. Olive recognizes that Ann is still grieving, and expresses her condolences. She still wonders why he chose to marry this woman.
That night, Olive tells Chris that she and Jack are getting married. Chris is angry, but Olive says he’s coming by the next morning to meet them. When Chris is sour to Jack the next day, Ann berates him for it in front of everyone, and Christopher apologies. When they leave, Olive thinks about how Ann yells at Christopher sometimes and realizes that Christopher has married someone like her. Olive realizes she has failed Christopher as a mother in some ways.
The Larkin house has burned to the ground. The Larkins are a couple who became shut-ins after their son, Doyle, was convicted and sent to prison for stabbing a girl 29 times. Roger Larkin, who was living on the top floor of the home, has died in the fire. (Louise Larkin has dementia and has been living in a nursing home.) Apparently two drug users broke in and tried to cook meth in the kitchen, resulting in a fire.
Suzanne Larkin, the daughter, has come home and meets with Bernie Green, her father’s lawyer. Suzanne works in the Attorney General’s office in child protection services. Suzanne confides in Bernie that she’s likely getting divorced soon because of an affair she had which she’s planning on admitting to her husband. Bernie suggest not telling him. Suzanne also worries that she’s mentally messed up from all this and will end up like her mother. Bernie suggests she find a therapist, but Suzanne says that was who her affair was with.
Bernie informs Suzanne that her father’s estate was substantial, but Bernie also admits to Suzanne that her father made much of that money by capitalizing on the apartheid situation in South Africa. Suzanne feels uncomfortable with it. At home, Bernie reflect on his years of covering or ignoring Roger Larkin’s misdeeds. Suzanne goes to see her mother who, in her reduced mental state, admits to molesting Doyle as a boy. Based on the reaction she gets from the clerk at the local motel, Suzanne pieces together that her father probably had various affairs and she worries she’s too much like him as well.
When Suzanne calls Bernie later, she says she is troubled knowing that in the last few years she has lost any semblance of faith. Bernie assures her that her faith will one day return, and Bernie feels a weight lifted off of him, seeing how guileless Suzanne has remained after all of this. Suzanne gets off the phone feeling contemplative and hopeful as well.
Cindy Coombs is in the grocery store and nearly slips and falls. Her former teacher from long ago, Olive Kitteridge, sees her and helps her with her shopping. Olive comes to check up on Cindy later, asking how her treatment is going. Cindy was a librarian before her illness. She admits to Olive that she feels angry, scared and alone at the prospect of dying. She feels irritated with her husband Tom.
Olive goes to visit Cindy again a few days later. Olive has now been married to Jack for two years now and they talk about her marriage. Cindy wonders what will happen if she dies, especially for her husband Tom. Olive assures her that even though she remarried she still misses her late husband Henry all the time.
Cindy has her last chemo treatment. Olive visits again, and Cindy notes that the only other person who still comes to see her is her sister-in-law, Anita (married to Tom’s brother). When Cindy expresses her frustration with Tom, Olive reminds Cindy that Tom is upset too right now and probably can’t concentrate on things.
Cindy realizes Olive is right and her pent up frustrations with Tom dissipates. As they sit there, they are both awed by the beauty of the sunset.
As Denny Pelletier takes a walk around Crosby at night, he thinks about his children who are all grown and moved away with children of their own. He thinks about how quiet the house is now. He also thinks about his life and how he’s spent his whole life just going along with things. He remembers Dorothy “Dorie” Paige, a beautiful girl he knew in high school. They had talked all the time for years, but he never made a move. Finally, she went off to college and killed herself not long after. A mutual friend later told Denny that Dorie’s father had sexually abused her growing up.
As he walks, he sees a man passed out on a bench. He calls 911, and the police confirm that the guy is on drugs and take him to a hospital. They note that Denny saved the guy’s life. As he goes home, Denny feels comforted knowing his kids grew up in a safe home. Denny notes that he’s been feeling down about the waning of his life, but feels more chipper with the reminder that it’s not over yet.
Jack, 79, and Olive, 78, have now been together for five years. When they first married, he realized Olive was very anxious all the time, but as the years have passed it has lessened which makes Jack happy. Recently he walked in on Olive, upset because she could no longer reach her toes to cut her nails. He ends up taking her to get a pedicure, which she enjoyed. One day, they decide to take a ride Shirley Falls, and they driving through the area where Henry grew up and around Olive’s childhood home as well.
They end up at a restaurant, when Elaine, the woman Jack once had an affair with when he was married to Betsy, walks in. Elaine tells them that she’s in town studying clitorectomy (female circumcision) because the town has a Somali population. After Jack and Olive leave, Jack thinks about how much he had loved Elaine. However, all the whie Elaine had been documenting their affair as evidence, and when Elaine failed to get tenure, Elaine filed suit and wound up with three hundred thousand dollars. Meanwhile, Jack was put on leave and didn’t return. Thinking about her puts Jack in a sour mood.
On the way back, Olive and Jack get into an argument and go to sleep angry. But when Jack wakes up disoriented in the middle of the night, Olive leads him back to bed.
(These characters are from Elizabeth Strout’s novel The Burgess Boys.)
Jim and Helen Burgess are New Yorkers who fly to Maine to drop off their eldest grandson, seven-year-old Ernie, at summer camp. Afterwards, they drive to Crosby to see Jim’s brother, Bob, and Bob’s wife, Margaret. (Bob was previously married to a woman named Pam, but his inability to father children ended the marriage.) Bob and Margaret had been living in Shirley Falls, but moved to Crosby. When Bob and Jim were very young, their father died in a car accident with them in the car. Only much, much later did Jim admit to Bob that he had been playing with the clutch which caused the accident.
Bob and Jim drive back to their childhood town of Shirley Falls, where their sister Susan still lives. Jim struggles with his guilt over a number of things: the accident, using medication and blaming his wife for it, and having an affair at one point. Meanwhile, Margaret and Helen attend a city art walk. Margaret is a Unitarian minister in town and many people stop her to say hi. When they get home, Helen slips on the stairs and falls, though she is okay.
Margaret feel guilty because she wasn’t very nice to Helen that day. She feels Helen is too rich and that makes her self-centered. It occurs to Bob that Margaret is prejudiced against Helen because of her wealth. As Helen rests, Bob thinks about how people are lonely and the things they do to keep them from feeling lonely. When Helen stirs in her sleep, Bob reassures her.
Olive is now 82. She drives to the marina to eat. She spots Andrea L’Rieux, a woman who left town and became a well-known writer and a Poet Laureate. Andrea invites Olive to join her. Andrea is back because her father has dementia and she has things to take care of. They have a nice meal, though Andrea seems a little sad, and Andrea gives Olive a hug when they part.
Jack and Olive has a trip to Oslo, and when they get back Olive hears that Andrea was in a serious accident, but survived. Olive wonders if Andrea had been trying to kill herself.
By the autumn, Jack has passed away. They ended up having eight years together. In May, a magazine arrives, including a poem by Andrea that has been bookmarked with a Post-It. Olive reads it and it’s about Andrea having breakfast with her former teacher. She describe Olive as projecting her feelings of loneliness onto her. Olive wonders who left that magazine in her mailbox. Later, Olive contemplates how far apart human experiences are. She also thinks about how she sees herself as someone who perceives things others don’t, but missed this. She wonders how well she ever knew Henry or Jack.
The End of the Civil War Days
The Fergus and Ethel MacPherson are a couple on the outskirts of town. Fergus MacPherson had an affair when they were younger, before divorce was widely accepted. The couple still lives in the house which is split with a piece of yellow duct tape. They have two daughters, Lisa (older) and Laurie (younger). Lisa visits home and announces she’ll be starring in a documentary about being a dominatrix. Fergus is upset. Lisa assures him she doesn’t have sex with any of the men, but it still results in a big argument.
Fergus is a Civil War reenactor, and they have an reenactment planned. He shows up an runs into Charlene Bibber, who he once had a dalliance with many years ago. He also sees Anita Coombs, who is having car problems and chats with her about how crazy the world has gotten. When he gets home, Ethel and the girls are watching the documentary. Fergus faints. When he comes to, Ethel comforts him, stroking his arm.
Olive wakes up in a hospital. The cardiologist, Dr. Rabolinski tells her she had a heart attack. Olive is kept in the ICU. Chris comes by to see her and arranges for home care. When she finally moves her bowels, she is allowed to go home. A few women show up to provide 24-hour care for Olive. When one woman, Betty (who has a Trump bumper sticker), is rude to the Kenyan woman, Halima, Olive gets mad at Betty.
Dr. Rabolinski comments that Olive must have been a very good mother, considering how often Chrisopher has come to check up on her. Everyone tells Olive she’s doing fine, but she’s sad and lonely.
One night Olive falls and has to force herself to get back up. Soon, Christopher plans to move her into assisted living. Before she moves, Betty drops by and they have a chat. Betty tells Olive about the difficulties in her life, and Olive feels a sort of love for Betty.
Olive is now living in assisted living. Olive feels her world getting smaller. Olive is not very popular there, and she thinks most of the residents are snobs. Bernie Green, who had handled the sale of Henry’s pharmacy is there, but cries all the time because his wife has Alzheimer’s. Ethel MacPherson is also there, and moved in after her husband died. She befriends a couple, the Chipmans, but they are a bit dull.
Christopher comes to visit with all his kids. When she asks for a typewriter and some rosebushes, he obediently brings them to her. Olive starts to type up her memories. Olive thinks about her mother who had a brain tumor and started behaving oddly. Her mother would go stroke her car like a horse, likely because it represented freedom for her.
Olive meets a woman she nicknamed Mouse Pants, whose real name turns out to be Isabelle Goodrow. Isabelle was raped by her father’s friend when she was young and ended up pregnant with a daughter Amy. Isabelle says she was not a good mother, but Amy loves her anyway. Olive says she wasn’t a good mother either. It turns out their kids are both doctors, and they both married pharmacists. Olive and Isabelle become friends. As she and Isabelle bond, Olive realizes she is not unhappy there. After Isabelle falls and hurts herself one day, they make a pact to check up on one another.
After Olive attends a funeral for a resident, Olive reflect on her life and how lucky she’s been. She wonders why anyone ever loved her. She writes a note on her typewriter “I do not have a clue who I have been. Truthfully, I do not understand a thing.” And then goes to fetch Isabelle for supper.