Ali is a 38-year-old professional organizer living in the New York suburb of Beechwood. Separated from her husband and grieving her late mother, she finds it difficult to manage her daily life or clean her own house. She decides to finalize her divorce and slowly reclaims her independence through small steps like wearing proper clothes and taking her dog to the park.

Ethan is a lawyer who runs a private practice and a community skate park in Devon, Massachusetts. He visits Beechwood to prepare his parents' house for sale. He forms a quick connection with Ali while helping her review legal documents. He listens closely to others and takes pride in his structured life in Devon.

Pete is Ali's estranged husband who moved out a year prior. He maintains an emotionally distant approach to parenting and frequently alters his visitation schedule to accommodate biking trips with friends. He attempts to manipulate their financial mediation to reduce his alimony obligations.

Fancy is Ali's late mother. She passed away two years prior. A spirited woman who loved hosting, she heavily influenced Ali's domestic choices and encouraged her to avoid marital conflict. Ali frequently holds internal conversations with her while attempting to untangle her own desires from her mother's expectations.

Frannie is Ali's lifelong best friend and the manager of Hogan Diner. She provides blunt advice and pushes Ali to engage with the outside world. She faces immense stress when her parents suddenly retire to Florida and leave her to manage their local businesses alone.

Phyllis is an elderly woman living next door to Ali in a matching twin house. She accepts Ali's daily help with meals but provides quiet wisdom in return. She observes Ali's personal changes and consistently encourages her to embrace happiness rather than fear.

Greer is Ali's oldest daughter. She was born shortly after Ali moved back to Beechwood from Manhattan. She is highly sensitive to the shifting dynamics between her parents and often internalizes the household stress.

Iris is Ali's middle daughter. She joins her siblings in their seasonal paddleboarding tradition and adapts to the new schedule of weekend visits at her father's apartment.

Cliffy is Ali's six-year-old son. He represents the final effort Ali and Pete made to save their marriage before their separation. He is energetic and enjoys practicing sports with his dad.

Lacey is the professional mediator tasked with formally dissolving Ali and Pete's marriage. She facilitates discussions regarding the house, assets, and custody schedules.

Marco is Frannie's husband. He works alongside her to keep Hogan Diner running smoothly while helping to raise their infant son.

Theo is Frannie and Marco's infant son. He is a frequent presence at the diner and occasionally stays with Ali when Frannie needs to handle business emergencies.

Ali's father lives nearby with his wife Libby. Though he was not heavily involved in Ali's childhood, he surprises her by offering genuine support and asking thoughtful questions during her divorce.

Libby is the wife of Ali's father. She has been part of the family for decades, though she and Ali maintain a polite but distant relationship.

Harold is the former beach attendant at the Beechwood Inn. Frannie's parents abruptly promote him to manager before moving to Florida, causing significant organizational problems.

Linda owns the boat rental operation on the Long Island Sound where Ali and her children celebrate the start of the summer season.