Olive Kitteridge is a retired math teacher, married to Henry, a pharmacist who is subservient to her demanding ways. They live in Crosby, Maine. Olive is well-known in town, but has few close friends. Olive and Henry have one child, Christopher, who moves far away because he can't stand to be near his overbearing mother. Olive's relationship with Suzanne, Christopher's wife, is strained, and the marriage eventually ends. When Christopher remarries and becomes a father, Olive tries to be flexible and accepting of Christopher's second wife, Ann. She wants to be part of their family and perhaps entice Christopher to move back to his hometown. When Henry suffers a stroke, Olive spends part of each day with him in the convalescent home, but he's unresponsive and beyond recovery. Alone and lonely, Olive meets Jack Kennison, who was not originally from the town of Crosby, so she perceives him as an outsider. She realizes that, although he's not perfect, she would rather spend the rest of her life with him than by herself.