Dolly is a 39-year-old single mother and kindergarten teacher who spends her summers in Whitfield, Rhode Island. She juggles multiple side jobs, including driving for Uber, to support herself and her 13-year-old son. As the primary caretaker for her father and brother, she instinctively manages everyone else's problems, often sacrificing her own needs. When her family home requires an expensive roof repair, she enters a fake-dating contract with a wealthy heir to secure the funds.

Stewart is the wealthy heir to Whitfield Industries, currently competing with his cousin for the CEO position. Recently humiliated after his fiancée publicly left him for a baseball player, he faces intense pressure from his family to project stability and strength. He offers to pay Dolly to pretend to be his girlfriend for the summer, initially viewing the arrangement as a strategic business transaction. Behind his composed exterior, he struggles with workaholism and anxiety regarding his dynastic legacy.

Gus is Dolly's 13-year-old son who has recently found himself feeling isolated from his peers in Boston. He struggles to fit in as his friends outgrow their shared interests, making him socially withdrawn. The move to Whitfield offers him a chance to start fresh at lifeguard camp, where he begins to build new connections and gain confidence.

Freddie is the proprietor of the Brick Fish House, a business that has been in his family for four generations. Burdened by debt from a failed expansion attempt years ago, he is highly risk-averse and resistant to change. He relies heavily on Dolly to manage household crises, though he harbors guilt over taking up so much of her time and energy.

Christopher is Dolly's 36-year-old brother who lives at home with their father. Diagnosed with schizophrenia secondary to a childhood brain injury, he requires a stable environment and constant care. He spends much of his time observing the town from the front porch and speaks with an unfiltered honesty that often cuts through social pleasantries.

Patsy is Dolly's younger sister who has built a life separate from the daily crises in Whitfield. Having escaped the heavy caretaking responsibilities that Dolly absorbed after their mother abandoned them, she maintains a conventional family life elsewhere. Her physical distance creates a quiet but persistent tension between the sisters.

Naomi is Dolly's best friend and the owner of a local gift shop called Whitfield Tees. Grounded in the town's working-class reality, she serves as a pragmatic and humorous confidante. She enthusiastically encourages Dolly to accept the fake-dating arrangement, seeing it as an opportunity for her friend to finally prioritize her own financial and personal needs.

Victoria is Stewart's mother and an ER doctor who resides at the lavish Eight Oaks estate. While she is part of a dynasty obsessed with maintaining social appearances, her medical profession keeps her connected to the practical realities of the town. She is observant of her son's well-being and scrutinizes his sudden relationship with Dolly.

Henry is the patriarch of the Whitfield family and a commanding presence on the board of Whitfield Industries. He is deeply critical of his son Stewart's business decisions and leadership capabilities. Demanding and traditional, he expects the family legacy to be upheld perfectly, creating immense pressure for the younger generation.

Busy is Stewart's enthusiastic and effervescent sister. A childhood cancer survivor, she now struggles to find a clear career direction and feels somewhat lost in adulthood. She eagerly steps in to help Dolly with a wardrobe makeover, viewing the fake-dating arrangement as an exciting project and treating Dolly with genuine warmth.

Grant is Stewart's cousin and direct competitor for the position of CEO at Whitfield Industries. He is sharp, ambitious, and quick to criticize Stewart's preservation-focused business deals. He actively monitors Stewart's personal and professional life, looking for weaknesses to exploit in their corporate rivalry.

Ellen is Grant's mother and a member of the older generation of the Whitfield dynasty. Unlike the younger, highly class-conscious family members, she maintains fond nostalgia for the town's working-class residents, particularly remembering the sewing skills of Dolly's grandmother.

Kendall is Grant's wife, a woman deeply invested in the social hierarchy of the Whitfield elite. She exhibits overt class consciousness and reacts with theatrical shock when she discovers that Stewart's new girlfriend comes from a local, working-class family that runs a fish market.

Audrey is Stewart's ex-fiancée who recently left him for a Yankees baseball player. Her public betrayal leaves Stewart looking weak in the eyes of his family and the corporate board, serving as the catalyst for his fake-dating arrangement with Dolly.

Gavin is the local fire chief in Whitfield. After extinguishing a small fire on the Bricks' sleeping porch, he delivers the devastating news that the entire roof is rotted and requires a massive repair to prevent the house from being condemned.

Clay is a local boy who quickly befriends Gus during the summer. He attends lifeguard camp with Gus and joins him on sailing trips, providing Gus with much-needed companionship and helping him transition to life in the coastal town.