Dolly All the Time (2026) is a contemporary romance novel by New York Times best-selling author Annabel Monaghan. Monaghan is known for her popular romance novels, including Nora Goes Off Script, a Reese’s Book Club selection, and Same Time Next Summer. Set in the fictional Rhode Island seaside town of Whitfield, Dolly All the Time follows 39-year-old single mother Dolly Brick, who spends her life solving problems for everyone around her. When a fire at her family home reveals the need for a costly roof repair, she agrees to a fake-dating arrangement with Stewart Whitfield, the wealthy and newly single heir to the town’s founding family, in exchange for the money to save the house.

Employing the popular fake-dating trope, the novel explores the vast social and emotional distances between inherited wealth and working-class realities. In addition to The Harmful Consequences of Class Division, the story examines the themes of The Burden of Caretaking and The Importance of Accepting Love and Support. As Dolly and Stewart’s transactional relationship evolves, the narrative contrasts her world of constant labor and self-reliance with his life of effortless privilege. Their arrangement forces both characters to confront their personal histories, family expectations, and deep-seated fears about vulnerability and failure, questioning whether a genuine connection can bridge the gap between their disparate lives.

This guide refers to the 2026 G. P. Putnam’s Sons edition.

Content Warning: The source material and guide features depictions of illness, mental illness, pregnancy termination, sexual content, substance use, and cursing.

Plot Summary

Dolly Brick, a 39-year-old single mother and kindergarten teacher, rushes from Boston to her childhood home in Whitfield, Rhode Island, after a small fire damages the family’s porch. Accompanied by her 13-year-old son, Gus, Dolly decides to stay for the summer to help her father, Freddie, at the Brick Fish House and to manage repairs. The situation becomes dire when the fire chief, Gavin McCumber, informs them the house’s entire roof is rotted and requires a $50,000 replacement to avoid being condemned. This financial crisis looms over Dolly, a self-reliant caretaker who juggles multiple jobs to make ends meet. While making a delivery to the lavish Whitfield estate, Eight Oaks, she encounters Stewart Whitfield, the handsome and newly single heir to the Whitfield family fortune, who is stranded with a flat tire. Dolly, ever the problem-solver, changes the tire for him, an act that is surreptitiously photographed by a paparazzo. The resulting photo appears in the New York Post with a fabricated headline claiming Stewart was teaching his new “gal pal” to change a tire, a story concocted by his sister, Busy, to save him from public humiliation after his fiancée, Audrey Mills, left him for a Yankees baseball player.

Stewart approaches Dolly with an unusual proposition: He wants to hire her to be his fake girlfriend for the summer. He explains that his image is critical as he vies with his cousin, Grant, for the CEO position at Whitfield Industries. His parents, who sit on the board, worry about his workaholic tendencies, and being publicly dumped has made him look weak. Desperate for the money to fix her family’s roof, Dolly agrees, negotiating a $60,000 fee. The arrangement begins with a whirlwind makeover, including a shopping trip with the effervescent Busy and a chic new haircut. Dolly and Stewart’s first public appearance is at a cancer fundraiser in Providence, where Dolly impresses the head of the charity, Jennifer Quigley, by fixing her torn dress in the restroom. At the event, Stewart delivers a heartfelt speech about Busy’s childhood battle with cancer, and the performative intimacy between him and Dolly begins to feel real. Their bond deepens during a sailing trip on Stewart’s boat, the Marian, where they discover a secluded grotto and share vulnerable stories about Dolly’s mother abandoning the family and Stewart’s fear of chaos stemming from his sister’s illness.

The connection between Dolly and Stewart grows increasingly genuine. He is a guest for dinner at her family’s humble home, where he bonds with her brother, Christopher, and especially with Gus, whom he invites to a Red Sox game. A subsequent sunset boat ride culminates in a series of passionate kisses in the boat’s galley. Frightened by the intensity of her feelings and the chasm between their lives, Dolly attempts to create distance by calling their kiss “method acting.” Despite this, their bond strengthens when Stewart insists Dolly accompany him to Boston for an important business dinner with the Kramer Corporation and his father, Henry. At the dinner, Dolly’s genuine nature help Stewart win over his skeptical father. The night ends at Dolly’s Boston apartment, where they confess their feelings are no longer just an act and sleep together. Their relationship blossoms into a real romance, with Stewart teaching Gus to sail and spending his nights secretly on Dolly’s porch. 

The arrangement is set to conclude at the Starlight Gala, the final social event of the summer held at Eight Oaks. Feeling like she is living a fairy tale, Dolly dances with Stewart, and they quietly acknowledge their love for one another. The dream shatters when Grant publicly exposes their financial contract, which he discovered after a conversation with Christopher. Henry is enraged by Stewart’s perceived deceit and poor judgment, calling Dolly a “call girl.” In the face of his father’s fury and his own terror of failure, Stewart panics. He fails to defend Dolly, focusing instead on the damage to his professional reputation. He walks away from her on the dance floor, leaving her publicly humiliated. Later, when she confronts him, he is cold and distant, telling her he doesn’t know what their future holds and offering to send the final payment. Heartbroken, Dolly realizes he has chosen his legacy over her, and she tells him to mail the check.

Dolly returns to Boston at the end of the summer, devastated. Months pass with no word from Stewart, except for the check delivered by a messenger. During a Thanksgiving visit to Whitfield, Dolly has a cathartic conversation with her sister, Patsy, and resolves to stop letting people hurt her without consequence. She decides to move back to Whitfield permanently. That winter, Gus is hospitalized with meningitis and is treated by Stewart’s mother, Victoria, a doctor. The crisis forges an unlikely friendship between the two women. Victoria reveals that Stewart is in therapy and has been trying to change his life. Empowered, Dolly goes to Stewart’s Boston office and confronts him, telling him he broke her heart. Nearly a year after the gala, Stewart appears at her family home. He apologizes, explaining that he had to confront his fear of failure and redefine himself outside of his family’s expectations. He reveals he has been secretly texting Gus for months, and he confesses he is still in love with Dolly. She admits her feelings remain but tells him it will take time to trust him again. The following day, he formally apologizes to her family and asks Gus for permission to date his mother. 

A year later, they are a happy couple. Stewart now runs a smaller preservation-focused arm of the family business from Whitfield, and Dolly has opened a successful bakery within the fish house. In the Eight Oaks vegetable garden, Stewart proposes to Dolly and asks to adopt Gus. Dolly says yes, finally at home with herself and the life she has built.