Tom is a lawyer and law professor in his fifties living in Westchester County. He approaches life with a detached, unaffected demeanor, often refusing to engage in emotional conflicts with his family. He harbors quiet resentment over his wife's past affair and views his impending empty nest as an opportunity to escape his current life. Lately, he has been experiencing mysterious physical symptoms like a swollen face and dizziness, which he stubbornly ignores.

Amy is Tom's wife, a woman struggling to cope with her youngest child leaving for college. She frequently bickers with her daughter and grows easily frustrated by her husband's emotional distance. Twelve years ago, she had an affair that permanently damaged the foundation of her marriage, leaving her anxious about her family's future as she faces an empty house.

Michael is Tom and Amy's adult son, who now lives and works in California. He acts as a mediator within his family, frequently stepping in to defuse arguments between his mother and sister. He shows deep concern for his father's failing health and tries to encourage Tom to reconsider his controversial professional choices.

Miriam, commonly called Miri, is Tom and Amy's 18-year-old daughter. She shares her father's laid-back, avoidant disposition, which causes constant friction with her mother. She heads off to study at Carnegie Mellon, leaving behind a high school relationship and unintentionally triggering her father's cross-country crisis.

Brian is Tom's former college basketball teammate who now lives in Denver. He shares many of Tom's conservative views and operates with a brazen, assertive personality. He reaches out to Tom with a professional opportunity involving a basketball player seeking to sue a sports league for discrimination.

Sam is an English professor and one of Tom's oldest college friends. Single and childless, he struggles to relate to Tom's complaints about marriage and parenting, focusing instead on his own academic career and dating life.

Eric is Tom's younger brother, separated by six years and a somewhat strained history. He is divorced and shares custody of his daughters, often feeling trapped by his circumstances while harboring lingering resentments toward Tom's perceived arrogance.

Jill is Tom's high school ex-girlfriend who now lives in Nevada with her daughter. She maintained a friendly correspondence with Tom after their breakup and quickly grows frustrated by his inability to express genuine emotion during his visit.

Todd is a young basketball player seeking legal representation to sue his sports league. He vocalizes bigoted beliefs about racial discrimination, forcing Tom to confront the reality of the clients he defends and the politics he supports.

Zach is a man from Amy's synagogue who engaged in a three-month affair with her when she struggled with fertility issues. His past involvement with Amy continues to cast a long shadow over the Layward marriage.

Jim is Miriam's high school boyfriend. He wants an open relationship during college, leading to their breakup before she leaves for Pennsylvania.

Terry is the owner of the Denver Nuggets. He faced suspension and fines for workplace sexual harassment and racism, and his decision to hire Tom resulted in intense public backlash that damaged Tom's reputation.

Betty is a close friend of Michael's who lives in Los Angeles. She joins Michael and Tom for meals and a trip to the beach, helping to care for Tom when he physically collapses.

Bianca was a student in the French club Amy once ran. She developed a dangerous obsession with Amy that culminated in a medical emergency and a threatened lawsuit, prompting Amy to quit teaching.

Tandy is Brian's wife, managing their household in Colorado. She warmly welcomes Tom into their home and offers him a place to stay during his cross-country drift.