Henry Kitteridge hires young Denise Thibodeau at his pharmacy after his previous assistant, Mrs. Granger, dies.

Denise's husband is accidentally shot and killed by his best friend during a hunting trip.

Kevin Coulson returns to Crosby with a rifle intending to die by suicide, but Olive intercepts him at the harbor.

Patty Howe falls into the harbor water, and Kevin dives in to pull her to safety.

Christopher Kitteridge marries Suzanne, and Olive eavesdrops as Suzanne mocks her dress and implies Christopher had a difficult upbringing.

Olive draws on Suzanne's sweater with a marker and steals several items from Suzanne's closet and dresser.

Armed robbers take Olive, Henry, and hospital staff hostage during what was meant to be a quick bathroom stop.

Olive and Henry have a devastating argument while held hostage that permanently alters how they see each other.

Henry suffers a stroke in a parking lot and is moved to a nursing home in an unresponsive state.

Olive visits the Larkin home and is deeply unsettled by Louise Larkin's disturbing insights into her state of mind.

Olive travels to New York to visit Christopher and meets his new pregnant wife, Ann, for the first time.

Christopher calmly tells Olive she has made people feel terrible; Olive rages and weeps until she is barely coherent.

A taxi arrives and takes Olive to the airport, abruptly ending her three-day visit to Christopher.

Olive finds Jack Kennison collapsed on her walking path by the river and stays with him until he recovers.

Olive lies beside Jack in his bed and realizes she is not yet ready to leave the world.

The story begins with Henry Kitteridge's pharmacy and his complicated attachment to young assistant Denise Thibodeau, ending in his quiet awareness of Olive's emotional affair with a colleague. Olive's most dramatic encounters unfold as she intervenes with a suicidal former student at the harbor and secretly vandalizes her son's new wife's belongings at their wedding. A hostage crisis at a local hospital exposes the deep fractures in Olive and Henry's marriage, while Henry's subsequent stroke leaves Olive profoundly isolated. Olive's attempt to reconnect with her son Christopher in New York ends in a shattering confrontation that forces her to face how others truly experience her. The novel closes with Olive finding unexpected companionship with widower Jack Kennison and arriving at a fragile but genuine will to keep living.

The headline events of Olive Kitteridge's life in Crosby.

Henry invites Denise and her husband to dinner at his home despite Olive's explicit disapproval.

Henry brings Denise a kitten to comfort her after her husband's death, and she names it Slippers.

Denise marries Jerry, the pharmacy delivery man, and moves with him to Texas.

Henry receives a birthday card from Denise signed with 'love' and reflects on the depth of Olive's grief for Jim O'Casey.

Angie O'Meara slips away from the piano for the first time in years and calls Malcolm at his home to end their affair.

Simon bends down and whispers to Angie at the piano that her mother once propositioned him in Boston.

Malcolm confronts Angie in the cold outside the bar and insists she call him at work when she sobers up.

Harmon watches Tim Burnham and Nina White strolling along Main Street and is charmed by the young couple.

Tim Burnham and Nina White are arrested in a drug bust, and Nina is revealed to have severe anorexia with heart damage.

Olive arrives at Daisy Foster's house to collect for the Red Cross and breaks down crying over Nina's condition.

Nina dies of a heart attack after relapsing from her eating disorder, devastating Harmon, Daisy, and Olive.

Harmon confesses his love to Daisy Foster in the wake of Nina's death, and Daisy accepts.

Bob and Jane Houlton attend a winter concert where Donna Granger casually mentions having met Bob in the Miami airport.

Bob confesses to Jane that he flew to Florida to visit his former mistress, who was sick with breast cancer.

Jane admits her fear of dying; the couple sit together in silence for a long time on the couch.

Henry Kitteridge's unspoken attachment to Denise Thibodeau shapes his inner life across years, from shared dinners and a gifted kitten to his eventual acceptance of her marriage and departure to Texas. Angie O'Meara's life as a barroom pianist reaches a turning point when she severs a long affair by phone and then absorbs a cruel revelation delivered by an old flame at the piano. A young couple, Tim and Nina, briefly captivate the community before their lives unravel in a drug arrest and Nina's worsening anorexia ultimately claims her life. Bob and Jane Houlton's long marriage is shaken when Jane pieces together evidence of a past infidelity at a winter concert, forcing them to confront their shared mortality. These stories of longing, betrayal, and fragile connection form the community tapestry that surrounds and gives meaning to Olive's own journey.

The secondary lives and quiet dramas surrounding Olive's world.

Denise accidentally runs over her kitten Slippers and calls Henry in tears; he goes to her and promises to take care of her.

Henry Kitteridge quietly understands that Olive had an emotional affair with Jim O'Casey after Jim dies in a car accident.

Olive reveals to Kevin Coulson that her own father died by suicide while they sit together in his parked car.

Angie O'Meara decides she will visit the church the next morning to play piano as she once did as a child.

Christopher reveals to Olive that he has considered suicide, deeply affecting her given her own father's history.

The young gunman removes his Halloween pig mask and begins to weep as police sirens draw close to the hospital.

After the hostage ordeal, Henry tells Olive they will never fully get over the things they said that night.

Christopher announces he is divorcing Suzanne but reveals he will stay in California rather than return home to Crosby.

Sitting alone at her kitchen table, Olive contemplates that she could kill herself at any time and leave no note.

Olive instinctively apologizes to Mary Blackwell in a parking lot and is shaken by the question of who she thought she was.

Olive finds Marlene Bonney sitting next to the unconscious Kerry Monroe and holding a knife against Kerry's neck.

Winnie Harwood lies for her escaping sister Julie and understands that her relationship with her mother has permanently changed.

Olive remembers her emotional affair with Jim O'Casey after learning that Christopher's upstairs tenant shares his surname.

Olive refuses to remove her shoes at airport security and is calmly led away by the guards.

Olive and Jack Kennison exchange emails after weeks of silence, each admitting their child feels estranged from them.

Hidden realizations and confessions drive this pool, beginning with Henry's silent understanding of Olive's affair with Jim O'Casey and Olive's own disclosure of her father's suicide to a man she suspects is planning the same. Christopher's confession of suicidal thoughts reminds Olive how closely mental illness shadows her family, while Angie O'Meara's small private decision to return to church marks her own quiet turning point. As Henry's stroke deepens Olive's isolation, she approaches despair before a chance near-collision in a parking lot triggers a startling and unexpected flash of self-reflection. A funeral confrontation, a runaway sister's secret, and a breakdown at airport security each mark moments where characters are forced into contact with truths they have long evaded. The pool closes with Olive and Jack's tentative email exchange — a small but significant step toward the connection that ultimately saves her life.