Dolly All the Time Summary: Fake Dating Summer Romance
TL;DR
A damaged roof, a stalled luxury car, and a summer of high-society events set the terms of a very unusual arrangement in Dolly All the Time by Annabel Monaghan.
The novel follows Dolly Brick, a thirty-nine-year-old kindergarten teacher and single mother, as she returns to her coastal hometown of Whitfield, Rhode Island, to help her family for the season.
What begins as a practical solution to a $50,000 repair bill turns into something far less simple for two people guarding old wounds.
Set against a New England resort town divided by class and history, the story pairs working-class pragmatism with dynastic expectation.
- Premise: A broke single mother agrees to fake-date a wealthy heir in exchange for a new roof.
- Setting: A New England coastal town split between locals on Goose Lane and the Whitfield dynasty at Eight Oaks.
- Tone: Warm, witty, and grounded in family drama rather than pure escapism.
- Central tension: Dolly’s instinct to carry every burden alone against Stewart’s fear of public failure.
- Key themes: Caretaking and self-sacrifice, asking for help, class divides, and healing from past abandonment.
- Structure: 41 chapters, with chapter 41 labeled “12 Months Later.”
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Book Snapshot
- Genre & Subgenre: Contemporary Romance / Romantic Comedy / Coastal Beach Read
- Core Narrative Tropes: Fake dating; wealthy heir and working-class heroine; forced proximity; summer romance
- Tone & Atmosphere: Witty, warm, humorous, tender, emotionally grounded
- Primary Conflict: Dolly’s habit of avoiding dependence versus Stewart’s fear of losing control of his family’s legacy
- Pacing Style: Character-driven and medium-paced, alternating light romantic scenes with family drama
- Publisher: G.P. Putnam’s Sons
- Publication Date: May 26, 2026
- Pages: 400
- ISBN-10: 0593853970
- ISBN-13: 978-0593853979
- Book Structure: 41 chapters, followed by Acknowledgments, a Discussion Guide, and an excerpt from It’s a Love Story
- Author Background: Annabel Monaghan writes contemporary romance, including Nora Goes Off Script, Same Time Next Summer, and Summer Romance.
Read the Full Chapter-by-Chapter Summary of Dolly All the Time Summary By Annabel Monaghan
Characters in This Book
| Character | Role |
|---|---|
| Dolly Brick | Thirty-nine-year-old kindergarten teacher, single mother, and family caretaker who returns to Whitfield for the summer |
| Stewart Whitfield | Executive and heir to the Whitfield real estate empire, competing for the CEO position |
| Freddie Brick | Dolly’s father and owner of Brick Fish House |
| Christopher Brick | Dolly’s thirty-six-year-old brother, who lives with a traumatic brain injury from a childhood car accident |
| Gus | Dolly’s thirteen-year-old son |
| Naomi | Dolly’s best friend, who manages Whitfield Tees |
| Busy Whitfield | Stewart’s younger sister and a childhood leukemia survivor |
| Victoria Whitfield | Stewart’s mother and an ER physician |
| Henry Whitfield | Stewart’s father and patriarch of Whitfield Industries |
| Grant Whitfield | Stewart’s cousin, also competing for the CEO position |
| Patsy | Dolly’s younger sister, who lives outside Boston |
| Gladys | Long-time housekeeper and cook at Eight Oaks |
| Izzy | Local contractor who completes the roof installation on the Brick house |
| Jen Quigley | Head of the Providence cancer center |
| Audrey Mills | Stewart’s ex-fiancée |
Dolly All the Time Summary: What Happens in the Book
Spoilers ahead. This section recounts the plot in full, including the ending.
Dolly Brick spends the school year in Boston as a kindergarten teacher, driving for Uber to support herself and her thirteen-year-old son, Gus.
She returns to her childhood home on Goose Lane in Whitfield, Rhode Island, for the summer to help her father, Freddie, run Brick Fish House.
Dolly has been her family’s primary caretaker since her mother, Georgia, left when Dolly was twelve. She also looks after her older brother, Christopher, who lives with a traumatic brain injury from a childhood car accident.
Soon after she arrives, a small electrical fire on the sleeping porch brings Fire Chief Gavin McCumber to inspect the house. He finds severe structural damage to the roof, which will cost $50,000 to replace.
Freddie’s business is just finishing its last debt payments, and he refuses to take on new debt or accept sacrifices from Dolly.
While delivering five pounds of shrimp to Eight Oaks, the Whitfield estate, Dolly finds Stewart Whitfield stranded with a flat tire on his 1994 Range Rover.
Unbothered by his wealth, she changes the tire herself. Stewart is an executive at Whitfield Industries whose ex-fiancée, Audrey Mills, recently left him for a Yankee baseball player, triggering a tabloid frenzy that threatens his bid for CEO against his cousin Grant.
Stewart proposes a discreet arrangement. Dolly will pose as his girlfriend at summer functions, including a Providence charity gala and private family dinners, to convince his parents and the board of his stability.
In exchange, he will pay her $50,000 plus a clothing allowance, solving the roof crisis. With help from Stewart’s sister Busy and Dolly’s best friend Naomi, Dolly gets a new bob haircut, a high-end summer wardrobe, and a yellow-and-rose gold dahlia necklace.
At a Providence cancer center gala, Dolly rescues a distressed event organizer by repairing her torn dress, earning genuine admiration from Stewart’s inner circle. During a sailing trip to Ruddy Duck Cove with Gus and his friend Clay, the two share personal histories.
Stewart reveals that Busy survived childhood cancer at age seven, which created his lifelong fear of family chaos. Dolly describes her mother’s sudden departure and her ex-partner Niles abandoning her during her pregnancy.
At a Boston dinner with Kramer Corp executives, Dolly impresses investors with a sharp “parking arbitrage” scheme.
The transactional agreement gradually becomes real intimacy, and Stewart bonds with Gus over baseball and backgammon while treating Christopher with warmth.
The tension breaks at the annual Starlight Gala at Eight Oaks. Grant, suspicious of the sudden romance, questions Christopher in the garage about the roof repair and then searches Stewart’s briefcase, finding the formal fake-dating contract.
Grant exposes the contract in front of Stewart’s family and gala guests. Panicked at the prospect of losing the CEO position, Stewart freezes and fails to defend Dolly or explain their real feelings.
Humiliated, Dolly removes her dahlia necklace, hands it to Busy, and walks away. Stewart briefly catches up outside, but retreats to an emergency board meeting and promises to mail a check instead of fighting for her.
Days later, a messenger delivers a $30,000 check for the remaining balance with no note. Dolly uses the funds to pay contractor Izzy to finish the new roof, but she is emotionally devastated.
Over Thanksgiving, she reconciles with her sister, Patsy, recognizing that her compulsive need to handle every burden alone had bred unspoken resentment and kept the family frozen in place.
She decides she wants a life centered on her own happiness rather than martyr-like sacrifice.
Dolly moves back to Whitfield permanently with Gus, takes a job as a substitute teacher, and plans a bakery expansion at the fish house.
Meanwhile, Stewart declines the corporate race, Grant is named CEO on a trial basis, and Stewart begins therapy with Dr. Meyers to address his control issues and fear of vulnerability.
In January, Victoria treats Gus at the hospital during a sudden illness and invites Dolly to Eight Oaks for tea. She apologizes for her son’s “weak move” and encourages Dolly to confront him.
Dolly and Naomi drive to Stewart’s Boston office, where Dolly bluntly tells him off for destroying a meaningful connection out of fear and hiding behind his work.
The following June, almost a year after they met, Stewart appears at Dolly’s sleeping porch at midnight.
He apologizes sincerely, explaining that he restructured Whitfield Industries to lead a smaller historic preservation division based in town and went into therapy. He realized he never truly wanted the corporate CEO title and only wanted her.
The next morning, Stewart visits the Brick home with a bouquet of flowers and asks Freddie, Christopher, and Gus for permission to pursue Dolly. He takes both families on a joint sailing trip to Nantucket, handing the helm to his brother Oscar.
At Eight Oaks, Stewart proposes to Dolly with his great-grandmother’s ring, expressing his desire to support Gus and build a shared future. Dolly accepts, stepping out of her solitary caretaker role and into a life where she is loved, supported, and allowed to be “Dolly all the time.”
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Quotes from Dolly All the Time
“For the caretakers. I wish I could bring you each a cup of tea just the way you like it.”
— Annabel Monaghan (Author Dedication)
“Dolly, I have a big job.”
— Stewart Whitfield (Explaining his position and responsibilities to Dolly during their initial negotiations on Main Street)
“She sends a holiday card with a lot of x’s and o’s. It’s like she’s our mom but she works remotely.”
— Dolly Brick (Describing her estranged mother, Georgia, to Stewart during their sailing trip)
“I’ve been that person in my family ever since… Fending off the chaos.”
— Dolly Brick and Stewart Whitfield (Discussing Dolly’s role as the family’s anchor after her mother left)
“I’m not a big hand-holder… Give me your hand.”
— Stewart Whitfield (Reaching out to Dolly in the town car after discussing dating habits)
“If you let me love you, I’ll never leave you again. If I have to leave, I’ll take you with me.”
— Stewart Whitfield (Expressing his permanent commitment to Dolly on her sleeping porch)
“I think you were put on this earth to make everything better.”
— Stewart Whitfield (Reflecting on Dolly’s nurturing nature before proposing to her at Eight Oaks)
Who Is Dolly All the Time For?
The novel suits readers of contemporary romance and romantic comedy who prefer character-driven stories over fast plotting.
The fake-dating premise and coastal summer setting provide the framework, while the emotional weight comes from family obligation, class friction, and long-held grief.
Readers who follow single-parent heroines, caretaker arcs, or small-town New England settings will recognize the territory.
Those looking for a light beach read should note that the book includes divorce, abandonment, childhood illness, and a public humiliation scene alongside its humor.
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Books Like Dolly All the Time
Nora Goes Off Script by Annabel Monaghan — Shares the author’s blend of witty adult romance, a resilient single mother, and a staged scenario that develops into real love.
Every Summer After by Carley Fortune — Features a nostalgic coastal setting, a summer romance timeline, and characters confronting family history.
The Flatshare by Beth O’Leary — Centers on a pragmatic arrangement between two opposites that becomes genuine affection and mutual healing.
Good Spirits by B. K. Borison — Offers warm character writing with fake-dating tropes, banter, and emotional comfort.
Beach Read by Emily Henry — Pairs two writers in a small lakeside town who strike a professional deal that shifts into something personal.
The Unhoneymooners by Christina Lauren — Uses a fake-relationship arrangement during a family trip as the starting point for an unexpected connection.
