Dolly All the Time by Annabel Monaghan: Fake Dating, Sailboats, and a Man Who Really Tested Our Patience
A $50,000 roof. A very rich man with a very rich man problem. Approximately 47 sailboats.
The world’s loosest NDA. And one woman who could probably survive the apocalypse using only the contents of her purse.
This week on Genre’d, we’re talking about Dolly All the Time by Annabel Monaghan, a contemporary romance filled with fake dating, old-money New England, family drama, lobster rolls, summer parties, eldest daughter burnout, and one third-act breakup that somehow got WORSE the longer we discussed it.
We also recorded this episode from Cape Cod over Labor Day weekend, which may have been the most aggressively on-theme setting possible for a book about a New England summer.
🚨 Spoiler Warning
The first part of the episode is spoiler-free, so you can absolutely listen if Dolly All the Time is still sitting on your TBR.
Once you hear the spoiler alarm?
All bets are off.
We get into the fake dating reveal, Stuart’s response, Dolly’s post-breakup era, whether therapy is enough to resurrect a ghost, and the exact moment both of our ratings started dropping in real time.
Consider yourself warned.
So, What Is Dolly All the Time About?
Dolly is thirty-nine, a single mom, a teacher, a professional-level problem solver, and the kind of person who has somehow spent her entire adult life taking care of everyone around her.
Then she returns to her hometown in Rhode Island for the summer after a fire at her father’s house reveals a much bigger problem.
The house needs a new roof.
A $50,000 new roof.
Her dad is finally getting out of debt. Her younger brother Christopher is deeply attached to the family home. And Dolly, being Dolly, immediately decides this is obviously her problem to solve.
Enter Stuart Whitfield.
Stuart is the heir to the wealthy family whose name is basically synonymous with the town.
He has money.
Dolly needs money.
Stuart also has a problem.
His family thinks he works too much and has no life, which is hurting his chances of becoming CEO of the family company.
So naturally:
Fake girlfriend.
Fake boyfriend.
Contract.
Roof money.
What could possibly go wrong?
Dolly Is Thirty-Nine and Fabulous, Thank You Very Much
One of our favorite things about this book was simply Dolly herself.
She’s thirty-nine.
She has a thirteen-year-old son.
She has friends.
She has a career.
She has an entire life that existed before Stuart Whitfield walked into it.
And the book does not treat any of this like a tragedy.
No ticking biological clock.
No “everyone else has settled down except me.”
No implication that she somehow failed because she reached almost forty without a husband.
She is just thirty-nine.
And fabulous.
We loved it.
Dolly is also unbelievably competent.
She works multiple jobs.
She raised her son largely on her own.
She helped raise her younger siblings.
She knows how to sew.
She can figure out how to change a tire.
She can run a business.
She probably has whatever emergency item you need somewhere in her purse.
Dolly’s biggest flaw is not that she cannot handle things.
It is that she is so good at handling things that she has convinced herself she should handle everything.
Eldest daughters, please form an orderly line.
Stuart Whitfield Is Exactly the Name of a Rich New England Man
We need to discuss the name.
Stuart Whitfield.
That is not simply a person.
That is a man whose family owns land.
That is a man who knows which fork to use.
That is a man who has access to multiple sailboats.
And yes, Stuart is the wealthy heir in this equation.
His family has been prominent in the town for generations, and Stuart has taken it upon himself to preserve the Whitfield legacy despite the fact that the rest of his family seems significantly less worried about it.
He works constantly.
He wants to become CEO.
He believes this is what he is supposed to do.
And when we meet him, his very public engagement has recently imploded after his fiancée starts seeing a Yankees player.
For a New England man?
Honestly, devastating on multiple levels.
Gus Deserves the Best Summer of His Life
Dolly’s thirteen-year-old son Gus quietly became one of our favorite characters.
He is at that horrible in-between age where some kids are still basically children and other kids have apparently jumped directly to high school nonsense.
He has been struggling socially in Boston.
Then he arrives in Rhode Island.
He makes friends.
He goes to lifeguard camp.
He gets into sailing.
He starts thriving.
And every single time something good happened for Gus, our reaction was basically:
DO NOT MESS THIS UP FOR GUS.
Gus also sees everything.
He knows Stuart likes his mother.
He knows when somebody is good news.
And frankly, if Gus approves of you, we are inclined to hear him out.
Naomi Would Have Had the Entire Town’s Gossip Before Breakfast
Then there’s Naomi.
Dolly’s hometown best friend stayed in Whitfield while Dolly moved away, owns a local clothing store, and appears to know essentially every piece of gossip occurring within town limits.
So when Dolly tells her she is suddenly dating STUART WHITFIELD?
Naomi needs details.
Immediately.
Then Dolly has to explain the whole fake dating arrangement.
Naturally Naomi signs the NDA.
Because apparently this contract had the security level of a middle school secret.
By the end, so many people knew about the arrangement that we were not entirely sure what the NDA was accomplishing anymore.
A Fake Dating Romance for Fake Dating People
Elyse loves fake dating.
This is established Genre’d lore.
And this book gives you the classic setup.
Very wealthy man needs girlfriend for reputation-related reasons.
Normal woman has an actual financial problem.
Business arrangement commences.
Fake intimacy becomes real intimacy.
Feelings ensue.
There is something about fake dating that conveniently solves the very difficult romance-novel question of:
How does this normal person end up spending enough time with a billionaire to fall in love with him?
Contract.
Done.
In Dolly’s case, she needs a roof.
Stuart needs to convince his family and the board that he can become CEO without working himself directly into an early grave.
Everyone gets something.
At least theoretically.
What It Was Giving
For Katy, this was giving a little JFK Jr. and Carolyn Bessette-Kennedy.
Ultra-prominent New England man.
Normal woman pulled into his very public world.
Old-money family.
Public fascination.
Except the Whitfields are considerably more welcoming to Dolly, and Dolly herself never seems particularly intimidated by the social divide.
Katy also landed on:
Pretty Woman meets Gilmore Girls meets a Newport tourism commercial.
Which feels correct.
You have the wealthy man / normal woman dynamic.
You have charming small-town New England.
You have family businesses and town gossip.
You have sailboats, fancy parties, summer weather, beach houses, and enough coastal atmosphere to make you immediately start Googling Rhode Island rentals.
Dolly’s Purse Deserves Its Own Supporting Character Credit
One of Katy’s favorite scenes happens at an early society event.
A woman has a wardrobe malfunction in the bathroom.
Most people would offer sympathy.
Dolly?
Dolly reaches into her purse, pulls out a sewing kit, and FIXES THE DRESS.
Because apparently she learned to make clothes for her siblings growing up.
Of course she did.
Of course she has a sewing kit.
Of course the person she helps turns out to be socially important.
This scene perfectly summarizes Dolly.
You want Dolly near you during an emergency.
If she does not know the solution immediately, give her three minutes.
She will figure it out.
The Shopping Scene Was a Personal Fantasy
After Dolly agrees to the arrangement, Stuart’s sister takes her shopping for all the events she now needs to attend.
And listen.
This is the dream.
Walk into a store.
Everything has been selected specifically for you.
Correct size.
Correct colors.
Beautiful clothes.
Champagne.
No fluorescent dressing-room lighting-induced emotional crisis.
And then someone ELSE pays the bill?
We would like to participate in this fake dating arrangement immediately.
New England Summer Is Basically a Character
We read this book at exactly the right time.
The setting does so much of the work.
The family fish market.
The houses.
The beach.
The boats.
The summer parties.
The sleeping porch.
The little islands and coves.
The whole thing feels deeply specific to a coastal New England summer.
We were literally recording in Cape Cod while discussing it, and there were multiple moments where we looked around the house and realized we had imagined scenes from the book looking almost exactly like the room we were sitting in.
There is something about a New England summer that feels slightly different from the Jersey Shore, the Hamptons, or Delaware.
And this book absolutely captures it.
🚨 SPOILERS AHEAD 🚨
Okay.
We need to talk about Stuart.
Because things were going extremely well.
Until they were not.
The Sailing Date Was Almost Too Cute
One of Elyse’s scene stealers happens when Stuart takes Dolly, Gus, and Gus’s new friend sailing.
Stuart, naturally, owns an unspecified but presumably ridiculous number of sailboats.
Because rich New England man.
The boys get to explore.
Dolly learns a little about sailing.
She and Stuart hike out to a hidden cove and waterfall.
They actually get to talk.
And for one beautiful moment, Stuart remembers there is a world outside of work.
This is also when his real conflict becomes obvious.
The problem is not that Stuart is rich.
The problem is that Stuart has convinced himself the entire Whitfield legacy rests personally on his shoulders.
Sir.
Go outside.
You own boats.
Use them.
And Then We Got to the Third-Act Breakup
This is where the episode took a turn.
Stuart is competing with his cousin Grant for the CEO position.
The board worries Stuart is too consumed by work.
Hence:
Fake girlfriend.
At the big Whitfield event near the end of their arrangement, Grant discovers the contract.
Then he exposes Stuart and Dolly publicly.
At this point?
They are no longer fake.
These people are in love.
Grant humiliates Dolly.
Stuart panics.
And instead of grabbing Dolly’s hand and saying, “We’re figuring this out together,” he basically shuts down.
Then he leaves.
And barely speaks to her.
Excuse us?
Stuart, You Cannot Just DISAPPEAR
Fake dating romances almost always have some version of the truth-coming-out moment.
Fine.
Expected.
Genre convention.
But Stuart’s response is what broke us.
Because this is not:
“I need the weekend to process this.”
This is not:
“I panicked, but three days later I realized I handled it terribly.”
This man basically ghosts Dolly.
FOR MONTHS.
He sends the rest of her roof money.
There are maybe a couple of texts.
But romantically?
Nothing.
Eventually Dolly has to go to HIS office with Naomi and tell him exactly what he did to her.
She delivers a great speech.
She stands up for herself.
And even then?
He does not immediately come after her.
When the Ghost Comes Back, That Is a Zombie
Eventually Stuart returns.
And yes.
He has done work.
Real work.
Therapy.
Self-reflection.
He stops obsessing over becoming CEO.
He chooses to lead a smaller sustainability-focused division.
He builds a healthier life.
He stays involved with Gus and helps support his interest in sailing.
We acknowledge all of this.
Growth!
Therapy!
Love it!
However.
There is an established rule.
When someone ghosts you and eventually comes back?
The ghost has become a zombie.
You do not welcome the zombie into your home.
You run.
This became a problem for us.
Because Stuart may be a good person.
But is he someone Dolly should trust with her heart again?
Different question.
We Needed More Groveling
This is what we kept coming back to.
If one of our friends said:
“This man told me he loved me, disappeared from my life for the better part of a year, and now he is back.”
Would we say:
“Aw, give him another chance!”
No.
We would say:
“BLOCK HIM.”
Possibly louder.
Yes, Stuart goes to therapy.
Yes, he changes his life.
Yes, Dolly does not immediately move him into the house.
But the amount of time matters.
When we were reading, the breakup somehow did not feel as long as it actually was.
Then we started mapping out the timeline during the episode.
And realized:
WAIT.
SHE WAS BASICALLY WITHOUT THIS MAN FOR AN ENTIRE YEAR?
This is where everything started falling apart.
Dolly’s Best Love Story Might Actually Be With Herself
The irony is that the breakup does force Dolly into the strongest part of her character arc.
Her entire life, Dolly has been the person who handles things.
Her family needs help?
Dolly.
Someone needs money?
Dolly figures it out.
Christopher needs stability?
Dolly.
Gus needs support?
Dolly.
Her dad refuses to change the family business?
Fine.
Dolly works around him.
But after Stuart disappears, something shifts.
She finally starts asking:
What do I want?
She decides she wants to live in Whitfield.
She stops waiting for her dad’s permission to change the fish market.
And she opens the bakery she has wanted to create.
It works.
People love it.
She builds something that belongs to her.
The real arc of Dolly All the Time is not Dolly finally finding someone who completes her.
Dolly was already complete.
Her arc is realizing she is allowed to make choices for herself instead of constantly organizing her life around everyone else’s needs.
The Title Actually Works Better Than We Expected
By the end, Dolly is comfortable simply being Dolly all the time.
Except...
She kind of always was?
That is part of what we loved about her.
Stuart does not teach her how to become independent.
She already is.
He does not teach her how to survive.
She could probably survive longer than him.
What changes is that Dolly stops treating her own wants as optional.
She can still love her family.
She can still help people.
She just does not have to sacrifice herself every time.
And honestly?
That is the more interesting happily ever after.
We Literally Talked Ourselves Out of a Four-Star Rating
This does not happen very often.
We both came into the episode thinking:
Four stars.
Easy.
Cute.
Well written.
Great setting.
Loved Dolly.
Fake dating.
Solid summer romance.
Then we talked about Stuart.
And kept talking about Stuart.
And realized how long Stuart had actually disappeared.
And suddenly we were invoking Bella Swan sitting in that chair while the seasons change in New Moon.
That is never good for a man’s rating.
By the end of the conversation?
Everything had changed.
Final Ratings
Katy
⭐️⭐️⭐️½
Katy genuinely liked this book more than she expected to.
The setting worked. Dolly felt like a real adult woman with an established life. The romance was grounded enough that it never became too exaggerated, and the writing made even the quieter parts engaging.
But the longer we talked about the breakup, the harder it became to imagine actually trusting Stuart again.
If this happened to one of our friends?
We would have some concerns.
Several.
Possibly a PowerPoint.
Elyse
⭐️⭐️⭐️½
Elyse was always primed to enjoy this because fake dating remains one of her favorite romance tropes.
Add in a gorgeous New England summer, a highly competent heroine, old-money society, and boats?
Easy sell.
But even Elyse could not completely defend Stuart once we really started unpacking the timeline.
The coziness and Dolly almost carried this to four stars.
Almost.
Stuart, you are lucky she took you back.
Fast Facts
Book: Dolly All the Time
Author: Annabel Monaghan
Genre: Contemporary Romance
Our Rating: ⭐️⭐️⭐️½ from both hosts
Expect:
Fake dating
Small-town romance
New England summer
Single mom FMC
Thirty-nine-year-old heroine
The world’s loosest NDA
A third-act breakup we are still discussing
Best for readers who want: A warm, character-driven fake dating romance with coastal New England vibes, an older heroine who already knows exactly who she is, and enough family drama to keep a relatively low-stakes romance interesting.
Next Up on Genre’d
Next up, we’re reading Exit Party by Emily St. John Mandel.
Elyse is especially excited because Station Eleven is one of her favorite books, and apparently Fantasy Fall can also include literary speculative fiction.
And dystopian fiction.
The definition is expanding rapidly.
We make the rules.
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Mini FAQ
Is Dolly All the Time a romance?
Yes. Dolly All the Time is a contemporary romance centered on a fake dating arrangement between Dolly and Stuart Whitfield.
Is Dolly All the Time spicy?
Not particularly. There are some intimate scenes, but this is a relatively low-spice romance and the relationship is much more focused on emotional connection than explicit content.
What tropes are in Dolly All the Time?
The biggest tropes include fake dating, rich guy / normal woman, small-town romance, single mom, old money, returning home, family responsibility, and workaholic hero.
How old is Dolly in Dolly All the Time?
Dolly is thirty-nine, which was one of our favorite aspects of the book. She is already established in her life, career, friendships, and motherhood before the romance begins.
Where does Dolly All the Time take place?
The story is set in a coastal Rhode Island town and leans heavily into its New England summer atmosphere, including beaches, sailboats, local businesses, family homes, and old-money society events.
Is Dolly All the Time a good beach read?
Absolutely. The coastal Rhode Island setting, summer romance, sailing scenes, small-town atmosphere, and relatively low-stakes plot make it a natural beach read.
Who should read Dolly All the Time?
Readers who like fake dating, adult heroines, coastal settings, low-spice contemporary romance, family-centered stories, and romances that feel more grounded than over-the-top will probably have a very good time with this one.
Readers with an extremely low tolerance for men who disappear for months may have additional thoughts.
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