Rather than existing in isolation, the characters in Olive Kitteridge exist in a complex matrix of interrelationships, though the links may not become apparent for several stories (or several decades of time in the story). The most common relationship is a family relationship or some reflection of a family.

The main character is Olive Kitteridge. In the collection, Olive passes from middle age through old age. During these years, she works as a seventh-grade math teacher, retires, becomes a wife and mother, then a caretaker of her husband Henry, who suffers a stroke, and finally a widow who is starting over. Author Elizabeth Strout takes readers past these surface descriptions of Olive and into her complex heart by showing Olive in a range of highly varied situations, and from perspectives that vary almost as much. When readers first encounter Olive in "Pharmacy," she seems causelessly cranky and unsympathetic to Henry's concerns. However, by "Incoming Tide," readers understand that she is deeply scarred by her father's suicide.

Strout's portrait of Olive grows more complex in "A Little Burst," when Olive overhears others talking about her and realizes how she—and her relationship with Henry—seems to the outside world. As a passing character in "Starving," Olive reveals surprising, almost metaphysical depth when she says to an anorexic girl that "we are all starving." What Olive in particular might be starving over is revealed under the intense pressure of being held at gunpoint in "A Different Road": Henry screams at her that she had taken over their son's life once her father died. Due to her pain and loss, and the desperate, often abrupt ways she deals with tragedies, Olive has created many of the negative aspects of the life she is left with.

Through these stories, Olive changes and grows, but self-knowledge only comes slowly, and growth does not always happen in expected directions. For example, harsh as she often is, Olive takes patient care of Henry for years after his stroke, seeing him every day. On the other hand, she is very judgmental of the women her son, Christopher, gets involved with, and seems stunned by his outburst toward her in "Security." Olive can deal with pain and external challenge in a matter-of-fact fashion. For example, when she finds Jim Kennison lying unconscious near the river, she asks him, "Are you dead?" However, Olive seems a clumsy stranger when dealing with her own emotions, overcome by stress in "Security" and surprised by love in "River." She is so distant from her own emotions that the one time she feels true passion, for Jim O'Casey, she never acts on it. She bears the scar of that loss too. Olive does her duty, but fits only poorly in the world, as out of place emotionally as she is oversized.

Olive shapes and is shaped by three people: Henry Kitteridge (her husband), Christopher Kitteridge (her son), and her father. Until...

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