Jack Kennison drives to the liquor store in Portland, Maine, an hour from his home in Crosby, to avoid seeing Olive Kitteridge while buying whiskey. He parks once he gets to Portland, and walks along the water. He sits on a bench and calls his daughter. It becomes clear that they are semi-estranged because he rejected her for being gay. Jack has lived in Crosby for six years and his wife, Betsy, died seven months ago. He goes to a bar in the basement of a hotel. He thinks about how his life and marriage might have been different had he and Betsy not married while both were rebounding from previous relationships.

He talks with the bartender, which makes him realize that he misses Olive Kitteridge because she is so forthright. Jack thinks of Olive. They had a strange relationship that was developing, but then Olive severed all communication. He has not spoken to her in about three weeks. While driving home, Jack thinks about his career as a professor. Jack retired from Harvard as a result of a sexual harassment suit filed by a colleague named Elaine. When he retired, he and Betsy moved to Crosby, at Betsy’s behest, even though they knew no one in the town.