Dolly All the Time by Annabel Monaghan

The fake-dating beach read with a single mom at the wheel.

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Annabel Monaghan's Dolly All the Time follows thirty-nine-year-old single mom Dolly Brick into a summer-long fake-dating arrangement with reclusive heir Stewart Whitfield. Beneath the Pretty Woman premise sits a tender, funny, sharply observed story about caretaker burnout, sibling resentment, and a heroine finally learning to stop carrying everyone before letting herself be carried.

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There is a moment early in Dolly All the Time by Annabel Monaghan when Dolly Brick, thirty-nine and biking through the wealthy Rhode Island town she grew up in, stops to change a flat tire for a man in a six-hundred-dollar shirt. The man is Stewart Whitfield. His family name is bolted to half the buildings in town, and Dolly used to deliver shrimp to his back gate from her father’s fish house. A photographer drives past. The photo lands in the New York Post the next morning. The deal is set in motion before anyone has decided to make one.

It is not, the book quickly tells you, Pretty Woman. Dolly’s best friend Naomi insists it absolutely is. Monaghan lets both readings sit on the page, which is a nice little wink to the long lineage of fake-dating arrangements that have powered romance fiction for decades.

The Plot, Spoiler-Free

Dolly has been called back to her hometown of Whitfield for the summer after a small fire at her father’s house. The roof needs replacing, her brother Christopher (who is disabled and lives with their dad) cannot lose this home, and her thirteen-year-old son Gus needs somewhere to be while she rebuilds the alarm system, the porch, and a few quietly cracked things in her own chest. She is a Boston kindergarten teacher with three side hustles and a notebook full of tasks she writes in blue ink and crosses out in green.

Stewart, freshly humiliated by a public breakup, needs a girlfriend for the summer to steady his image at work. He pays. She delivers a shrimp order, signs an NDA, and starts wearing dresses that did not come from her sister’s old closet.

What follows is summer in a fictional town that sits where Newport would be if Monaghan had not gently elbowed it over a few miles to make room. Yacht-club dinners. Borrowed dresses. A haircut Dolly does not entirely love. An estate called Eight Oaks where the front gates carry gold acorns the size of a person’s head.

Where the Voice Earns Its Pay

Dolly’s first-person narration is the engine of Dolly All the Time by Annabel Monaghan, and Monaghan tunes it with real care. Dolly is funny the way exhausted people are funny: by accident, and then with intent. She runs on lists, coffee, sarcasm, and a stubborn refusal to ask for help, which Monaghan turns into both joke and ache.

A few of the small textures that make her land as a real person on the page:

  • Her green-pen system for her to-do list. Green means go.
  • A “Bad Teachers” group text with her colleagues from school that runs as a kind of Greek chorus through the summer.
  • The way she calls her recorded-line call center side hustle her side hustle without irony.
  • The shrimp she carries to the back door of Eight Oaks the first night she is invited as a guest, because old habits.
  • Her son Gus’s ritual of swapping ice cream cones halfway through. Time for the plot twist, he says every time.

You finish a chapter and you know what is in her freezer.

The Romance: A Slow Hum Rather Than a Spark

Stewart is the part of the book that asks you for patience. He is a workaholic, a serious person, a man who answers texts in clipped one-liners and brings Page Six to his fiancée’s table at breakfast. Monaghan writes him as someone who learned to hold off chaos by working through every hour of every day. The thaw arrives in increments rather than in scenes.

The chemistry, when it shows up, is built from small things. A handkerchief offered for grease on a forehead. A yacht detour to a deserted cove. A backgammon board set up in a kitchen because somebody’s kid hit his head on a rock and needed an adult who was not panicking. There are no fireworks here, and the book is the better for it. It trusts its premise to do its job.

What Annabel Monaghan Fans Will Recognize

Readers who came in through Nora Goes Off Script or stayed for Same Time Next Summer and Summer Romance know the Monaghan house style. A competent woman in a small coastal town. A man who is not what she expected. A domestic life rendered in clean, specific sentences. Dolly All the Time by Annabel Monaghan sits comfortably in that lineup.

Specific Monaghan signatures on display here:

  1. A single-mother heroine carrying more than her share, written without pity.
  2. A child character who is funny on his own terms, not just as a plot lever.
  3. A best friend whose dialogue runs significantly more chaotic than the narrator’s.
  4. A small town that feels lived in down to which park bench sits across from which ice cream shop.

If you wanted more sailing this time, Monaghan has given you the sailing.

Where the Book Could Have Pressed Harder

A four-star average tracks honestly with what the book is and what it sets out to do. A few notes from a reader who finished it across two long evenings:

The premise has bones any frequent romance reader will recognize from a hundred paces. Monaghan does not try to subvert the fake-dating trope so much as honor it, which is fine, but it does mean the middle moves on rails you can see from the first chapter. A public misunderstanding, a third-act distancing, a reconciliation built around a single gesture. The order of those events will surprise nobody.

Stewart, for all his careful drawing, stays slightly less vivid than Dolly. His interior life filters almost entirely through her, and the moments when he speaks for himself are still calibrated to what she needs to hear in that scene. A reader who comes to romance hoping for two equally rendered points of view may find the balance off.

Christopher, the disabled brother, is treated with real tenderness, but the book uses him most often as a fixed point of love and worry rather than as a character with full agency. Monaghan handles him better than most romance novels would, and it still feels like there is more on the page he could have been.

Victoria, the mother-in-law in waiting, deserves a small standing ovation. She arrives looking like a type and ends up being one of the most surprising people in the book.

Comparable Reads If You Loved This One

If you finish Dolly All the Time by Annabel Monaghan and want the same air in your lungs, try these next:

  1. Nora Goes Off Script by Annabel Monaghan, for the same single-mother-meets-impossibly-handsome-man energy.
  2. Same Time Next Summer by Annabel Monaghan, for the coastal nostalgia and second-chance pacing.
  3. Summer Romance by Annabel Monaghan, for the recently-unraveling heroine in a small town.
  4. Beach Read by Emily Henry, for two reserved people thawing across a small body of water.
  5. Funny Story by Emily Henry, for the messy aftermath of a public breakup.
  6. Romantic Comedy by Curtis Sittenfeld, for a smart narrator who keeps catching herself being charmed.
  7. The Wedding Date by Jasmine Guillory, for the fake-dating-for-a-public-occasion mechanics.

Who This Book Is For

Pick up Dolly All the Time by Annabel Monaghan if you want a romance that takes caretaking seriously, that puts a thirty-nine-year-old single mother at the center without apology, and that resolves with both feet on the ground. Pass if you want spice on every other page or a heroine without responsibilities. The book is wearing its summer dress. It is also wearing sneakers underneath.

By the time Dolly is on the porch swing at Eight Oaks watching her son learn to sail, the book has answered its central question. Can a woman who has held the whole house up by herself ever let someone else do some of the holding? Yes, with a small amount of new bruising and a lot of new air to breathe. The title turns out to be a promise the book quietly keeps.

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Annabel Monaghan's Dolly All the Time follows thirty-nine-year-old single mom Dolly Brick into a summer-long fake-dating arrangement with reclusive heir Stewart Whitfield. Beneath the Pretty Woman premise sits a tender, funny, sharply observed story about caretaker burnout, sibling resentment, and a heroine finally learning to stop carrying everyone before letting herself be carried.Dolly All the Time by Annabel Monaghan