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The idea arrived in the fall of 2020, when almost no one was meeting anyone indoors. Hilderbrand was at a restaurant with a fellow writer, one of the only two people there, when her friend described something she had just witnessed: a woman with a terminal diagnosis had gathered the most important people from across her life for one last weekend on Nantucket, and the guests were not getting along. The friend’s aside about what kind of story that was became the book’s starting pistol.
Oh my goodness, this is a novel.
The terminal diagnosis gave the premise its urgency, but it was not what Hilderbrand kept returning to as she planned the book. The dramatic charge she found underneath the premise was structural: what happens when the different, compartmentalized versions of a life are forced into the same room at the same time.
What I attached to was the idea of inviting your closest friend from each phase of your life, because as we get older, our circumstances change, we grow, and our friendships change. And what would it be like to invite people from different stages of your life — would they get along, would there be drama? Because they don’t know each other. [paraphrased from audio]
The book’s most emotionally raw character, Caroline, is the dead husband’s teenage daughter, a girl whose grief curdles into fury at her mother. Writing her required almost no research. Hilderbrand lost her own father to a plane crash at sixteen, and one line she gave Caroline turned out to be a line she had said herself, in her own kitchen, to her own mother.
I lost my dad when I was 16, so Caroline was really easy for me to write. There is a line where she says [to Hollis], ‘You can get another husband. I’m never going to have another dad.’ I think I said that exact line to my mom. I can remember feeling like I have lost somebody irreplaceable.
The conceit of the book demands one close friend from each distinct chapter of Hollis’s life: childhood, college, early adulthood, and middle age. The first three categories yield natural candidates, but the last one exposed a real social problem that Hilderbrand had to solve on the page before the dynamics of the weekend could even begin.
It’s hardest to meet new friends when you’re in middle age because the kids are grown and maybe you work from home. That’s why we included the Gigi character.
Hollis herself, the widowed food blogger and host at the center of the novel, needed a specific cultural reference point so readers would immediately feel her warmth and authority. Hilderbrand reached for a recognizable archetype from the world of food media, then adjusted the details until the character felt like her own.
I was thinking of an Ina Garten type, because her fans feel like they’re in good hands with her in the kitchen. But she’s older than Hollis. And Hollis is a blonde. She looks a little bit like me.
When the Peacock adaptation went into production, casting conversations began, and Hilderbrand was firm about one habit she does not break. Writing characters toward real performers is a trap she has avoided across her career, and she held that line here even as the television version took shape around her.
It’s so dangerous because then you’re writing for an actress and not for the story. It is always better to write for the book and let the actors fit into the narrative rather than write for the actors and have the narrative fit them.
The principle reflects how seriously she treats the book as an object separate from any screen version. The story comes first; everything else adapts to it.
Caroline’s anger at her mother is one of the novel’s most uncomfortable dynamics to read, and it is also the one Hilderbrand understood from the inside. The specific emotional logic, the sense that a daughter’s loss is categorically different from a widow’s loss, came from her own adolescence rather than from any research or imagination.
I lost my dad when I was 16, so Caroline was really easy for me to write. There is a line where she says [to Hollis], ‘You can get another husband. I’m never going to have another dad.’ I think I said that exact line to my mom. I can remember feeling like I have lost somebody irreplaceable.
The friendship framework of the novel also doubled as a form of personal inventory. Assembling Hollis’s guest list made Hilderbrand map her own, and the question the book poses to its protagonist became a question she was asking herself at the same time.
I feel like it’s a celebration of women’s friendship, and an acknowledgement of the fact that we do change — my friends from high school are very different from the friends I have now. And their only common ground is me, and so it’s such an interesting dynamic. And it did make me think: who would you invite when you think about your life? [paraphrased from audio]
Hilderbrand’s books are reliably shelved under beach read, a label that has followed her for three decades and that she has spent those same decades quietly pushing against. With this novel, she made the counter-argument explicit.
I’ve never wanted my stories to be cheesy or silly or easy-breezy, even though they’ve been called that. I want them to have real things and real nuance. And The Five-Star Weekend is complicated in a way that everybody can relate to.
Nantucket, where Hilderbrand has lived year-round since 1994, is not incidental decoration in this book or in any of her novels. When the Peacock adaptation secured permission to film on the island rather than substituting a cheaper location, her reaction measured exactly how much the place means to the work.
The most wonderful thing other than the birth of my children was having ‘Five Stars’ shot on Nantucket because it is a singular place, it is unique and you can’t really imitate it.
The invitation at the heart of the novel is not just Hollis’s logistical problem. Hilderbrand built the premise so that readers would turn it over and apply it to their own lives, measuring the distance between who they were in each chapter and who their friendships reflect now.
I feel like it’s a celebration of women’s friendship, and an acknowledgement of the fact that we do change — my friends from high school are very different from the friends I have now. And their only common ground is me, and so it’s such an interesting dynamic. And it did make me think: who would you invite when you think about your life? [paraphrased from audio]
The book’s warmth and its difficulty are not in tension. The complication, a daughter’s raw grief, friendships that curdle under pressure, a widow navigating what comes next, is exactly what Hilderbrand wanted the reader to carry out of the reading experience.
I’ve never wanted my stories to be cheesy or silly or easy-breezy, even though they’ve been called that. I want them to have real things and real nuance. And The Five-Star Weekend is complicated in a way that everybody can relate to.
The novel invites readers to enjoy the Nantucket weekend and then sit with what it actually cost the people living it.