Jack Kennison, a seventy-four-year-old widower and retired Harvard professor, drives to Portland to buy whiskey to avoid the possibility of running into Olive, who he has since separated from, at the grocery store in Crosby.

One of the pregnant guests goes into labor and Olive attempts to drive her to the hospital, but finds herself having to deliver the stranger's baby in the back of her own car.

While cleaning the house of Mrs. Ringrose for money, Kayley begins experiencing sexual feelings and touches her breasts.

In the last days of summer, Kayley learns from Olive Kitteridge that Mr. Ringrose's behavior has become abnormal and he is being put in a nursing home.

Two days before Kayley begins high school, she rides her bike near the nursing home and feels a longing for Mr. Ringrose.

Olive invites her son Christopher, a podiatrist living in New York, to finally come visit Crosby with his wife, Ann, and their four children.

Olive reflects that she has "failed on a colossal level" with both Henry and their son Christopher and has "lived her life as though blind."

Suzanne Larkin returns to Crosby, where her childhood home recently burned down with her father having died in the process.

Denny stumbles upon a man bent over a bench and calls the police, who arrive and intervene by injecting him with Naloxone.

Their silence and separation is somewhat broken when their older daughter, Lisa, returns from Portland to tell them she has become a dominatrix and is the star of a new documentary.

The story draws parallels between the performance aspect of Fergus' Civil War reenactments with their daughter's work as a dominatrix.

Christopher visits Olive frequently and eventually helps her get into Maple Tree Apartments, an assisted living facility.

[10] In the January/February 2020 issue of Bookmarks, the book received 4.0 out of 5 stars, with the critical summary saying, "Her's are stories of memory, relationships, loneliness, and the ordinary moments of people's life, and Olive is "as indelible and lifelike a creation as you'll find in contemporary fiction" (Entertainment Weekly)".

[11][12] Kirkus Reviews praised the novel, writing, "Beautifully written and alive with compassion, at times almost unbearably poignant.

"[14] In her review for The Washington Post, Joan Frank gave the novel a positive review, calling it "arguably better than the original" and writing, "Sentences flow in simplest words and clearest order — yet line after line hammers home some of the most complex human rawness you'll ever read.