The book is a collection of 13 interconnected short stories revolving around Olive Kitteridge, a retired schoolteacher living in a small town in Maine. Olive is a complex character with a prickly exterior but a deep well of emotion and empathy beneath the surface. Through her interactions and relationships with various town residents, the book explores themes of love, loss, aging, and change, painting a rich portrait of a community and its inhabitants.

"Who Do You Think You Are?" is a collection of short stories that follow the life of a woman named Rose from her childhood in rural Ontario through her adulthood as she navigates the complexities of relationships, personal identity, and social class. The stories explore themes of self-discovery, the nature of memory, and the impact of personal history on one's present. The narrative is a deep exploration of the human condition, revealing the intricacies of the protagonist's experiences, emotions, and perceptions.

"The Progress of Love" is a collection of short stories that explore the complexities of human relationships, particularly focusing on love. Set in various locations, from small-town Ontario to post-war Italy, the narratives delve into the lives of different characters as they navigate the intricacies of love, loss, and the human condition. The stories intricately weave together themes of memory, time, and the constant evolution of love, showcasing the author's ability to portray the subtleties of everyday life with profound insight and empathy.

"Runaway" is a collection of short stories that explore the depth of human relationships, the complexities of love, and the consequences of life's unpredictable turns. The stories revolve around women of varying ages and circumstances, each dealing with her own unique situation. Some are escaping from their past or present situations, while others are struggling to find their place in the world. The narratives delve into themes like betrayal, loss, and the often complicated dynamics between parents and children, and husbands and wives.

"Open Secrets: Stories" is a collection of eight short stories that delve into the complex lives of women, exploring themes of love, loss, and the secrets that bind and divide people. Set in various locations, from small-town Ontario to Australia, the stories feature characters grappling with their pasts, negotiating relationships, and confronting the mysteries of life. The narrative oscillates between past and present, revealing the profound and often unsettling truths hidden beneath the surface of ordinary lives.

"Hateship, Friendship, Courtship, Loveship, Marriage" is a collection of nine short stories that explore the complexities of human relationships. Each story delves into the intricate web of emotions and experiences that define the human condition, including love, hate, friendship, courtship, and marriage. The characters are rendered with depth and nuance, their lives marked by moments of profound change and subtle transformation. The stories are set against the backdrop of rural and urban landscapes, offering a rich, evocative portrayal of life in all its complexities and contradictions.

"Reasons to Live" is a collection of short stories that depict various characters grappling with loss, grief, and existential crises. The narratives are filled with dark humor, sharp observations, and profound insights into the human condition. The stories explore themes such as death, suicide, and mental illness, but they also highlight the resilience of the human spirit and the potential for healing and redemption.

"The Love of a Good Woman" is a collection of eight short stories, each delving into the complex nature of relationships, particularly focusing on women. The narratives explore various themes such as love, betrayal, death, and the often overlooked intricacies of everyday life. Set in small-town Canada, the stories are filled with characters grappling with their desires, secrets, and the unexpected turns of life, offering a profound and nuanced exploration of human behavior and emotions.

"Anything is Possible" is a collection of interconnected stories exploring the lives and struggles of various residents in a small town in Illinois. The stories delve into the characters' pasts, revealing their secrets, regrets, and the complexities of their relationships. The book explores themes of poverty, trauma, and the human capacity for change, demonstrating that despite hardships and heartbreak, anything is possible.