Olive is an irritable, seventy-something former math teacher living in Crosby, Maine. She faces the recent loss of her first husband and a strained relationship with her adult son. Despite her brusque exterior and tendency to offend others, she possesses a keen eye for truth and a surprising capacity to assist people in distress.

Jack is a wealthy, retired Harvard professor and a Republican who relocated to Crosby with his late wife. He feels isolated and estranged from his gay daughter, making him increasingly reliant on his unexpected connection with Olive. He values her absolute bluntness, finding it a relief from his own internal anxieties and past mistakes.

Cindy is a former librarian facing grueling treatment for cancer. Confronting a frightening prognosis, she feels alienated by her family's inability to discuss her potential mortality. She finds an unlikely source of comfort in Olive, whose refusal to sugarcoat reality provides her with much-needed grounding.

Fergus is an older resident of Crosby who proudly embraces his Scottish heritage by wearing a kilt around town. He feels increasingly disconnected from modern society, a disconnect that mirrors his heavily compartmentalized domestic life. He shares a house with his estranged wife, living in strictly divided zones.

Denny is a sixty-nine-year-old retired mill and clothing store worker of French-Canadian descent. He carries a quiet sense of discontent about his winding-down life and worries excessively about his stable, adult children. He bears the silent weight of the prejudice he faced in his youth.

Christopher is Olive's adult son, managing his own growing family while maintaining a tense, distant relationship with his mother. He harbors deep-seated resentment toward Olive's parenting style. He often reacts defensively to her bluntness and her new romantic relationship.

Ann is Christopher's wife and a mother who favors modern parenting techniques, like planning a water birth. She openly dislikes Olive and makes little effort to hide her hostility during family visits, occasionally erupting in anger when provoked.

Henry is Olive's late first husband. Though deceased, his memory heavily influences Olive's current reflections on her past behavior. He was a pharmacist who endured Olive's difficult temper throughout their long marriage.

Kayley is a fourteen-year-old middle school student who works part-time cleaning houses for senior citizens in Crosby. Grieving the death of her father, she manages the confusing behavior of the wealthy adults who employ her. She possesses a quiet intelligence and a strong sense of her Irish heritage.

Mrs. Ringrose is an English teacher and a proud descendant of the Mayflower. She lives in the past, heavily focused on her ancestry and historical artifacts. She hires Kayley to clean her home but frequently leaves her alone there.

Mr. Ringrose is the older husband of Kayley's teacher. He exhibits inappropriate behavior around Kayley when his wife is not present, utilizing money to ensure her silence.

Suzanne is a lawyer specializing in child protection who carries significant trauma from her family's dark history. Returning to Crosby after her childhood home burns down, she seeks counsel from her family's lawyer regarding her complicated inheritance and her own personal mistakes.

Bernie is an elderly lawyer in Crosby who serves as a confidant and secret-keeper for the town's residents. As a Jewish immigrant who lost his parents in the Holocaust, he offers a grounded, pragmatic perspective to clients like Suzanne who struggle with guilt and faith.

Tom is Cindy's husband. He attempts to cope with his wife's severe illness by maintaining a facade of optimism, a coping mechanism that unintentionally isolates Cindy. He struggles to manage his own quiet grief and fear.

Marie is Denny Pelletier's wife. She enjoys a quiet retirement with her husband, sharing a comfortable but somewhat silent domestic routine after raising their children.

Elaine is a professor at Smith College and a former colleague of Jack's from Harvard. She represents a difficult chapter in Jack's professional and personal past, acting as a catalyst for his self-reflection regarding his previous behavior.

Jim is a successful lawyer who left Maine to build a life in New York. He carries longstanding guilt regarding a childhood tragedy that profoundly shaped his and his brother's identities. He struggles with depression, which prompts his unexpected visit to Crosby.

Helen is Jim's wealthy, city-dwelling wife. She feels out of place and deeply awkward in rural Maine, masking her shyness by talking excessively about her grandchildren and drinking wine.

Bob is Jim's brother and a local lawyer. He lives under the shadow of a childhood accident, an event that defined his self-image for decades. He possesses a gentle demeanor and attempts to keep the peace between his wife and his visiting family.

Margaret is Bob's wife. She harbors a strong prejudice against wealthy urbanites and makes little effort to hide her distaste for Helen during their visit. She fundamentally misunderstands Helen's nervous behavior as self-centered arrogance.

Andrea is a famous poet and a former math student of Olive's. Returning to Crosby due to her father's illness, she engages in a revealing conversation with her former teacher, eventually using the encounter as inspiration for her work.

Ethel is Fergus's wife. Following an old betrayal, she has spent over three decades sharing a home with Fergus without speaking to him directly, maintaining a rigid boundary of tape to divide their living space.

Lisa is Fergus and Ethel's adult daughter. She visits her parents to inform them of her unconventional profession and a documentary being made about her, hoping to educate them despite their traditional viewpoints.

Betty is a home health nurse and a former student of Olive's. She holds political views that deeply offend Olive and behaves rudely toward her coworkers, though she harbors her own private griefs and unrequited loves.

Halima is a home health nurse of Somali descent who assists Olive during her recovery. She faces hostility from her colleague Betty but forms a tentative, respectful connection with Olive.

Isabel is a resident of the local senior apartments who befriends Olive. Characterized by her striking honesty, she bonds with Olive over their shared physical vulnerabilities and complex histories with their children.

Betsy is Jack's deceased first wife. Though gone, her hidden past and the secrets she kept severely disrupt Jack's understanding of their marriage and his own self-awareness.