Gather initial thoughts and broad opinions about the book.

1. The story is built around the popular fake dating trope. How effectively do you think the novel used this convention? Have you read other books that use this setup, like Ali Hazelwood’s The Love Hypothesis, and how did this one compare?

2. What was your initial impression of Dolly and Stewart when they first met on the side of the road? Did you find yourself rooting for them as a couple from the beginning, or did your feelings about their relationship change as the story unfolded?

3. Monaghan is known for her heartfelt summer romances like Nora Goes Off Script. If you’ve read her other work, how does Dolly All the Time fit with her style? What signature elements of her writing did you notice, and what, if anything, felt different about this story?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Dolly’s identity is deeply connected to her role as a caretaker. Share about a time when a role you played, whether in your family, work, or community, started to define you. What did you learn from this experience?

2. Dolly compares herself to a “Comfort Inn” and Stewart to a “Four Seasons.” Have you ever felt a similar sense of not quite belonging in a particular social or professional setting, and how did you navigate those feelings?

3. Stewart lives with a deep-seated fear of failing to live up to his family’s legacy. In what ways do external expectations, whether from family, society, or work, shape your choices and sense of self?

4. A major part of Dolly’s journey is learning to accept help and support from others. In your own life, do you find it easy or difficult to let others share your burdens?

5. Gus blossoms in Whitfield, finding friends and new passions after feeling isolated in Boston. Think about a place or community that has made you feel truly at home. What elements helped you feel like you belonged?

6. The conversation between Dolly and Patsy near the end of the book is a difficult but important turning point for their relationship. Can you recall a time when an honest, perhaps overdue, conversation with a loved one helped clear the air and lead to a new understanding?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. How does the novel use the Gilded Age history of its Newport-inspired setting to comment on class divisions? Where do you see similar tensions between the wealthy and the working class today?

2. What does Stewart’s initial proposal to hire Dolly suggest about the intersection of money, power, and relationships? How does the story critique the idea that anything, even a relationship, can be transactional?

3. The Whitfield family is driven by the immense pressure of upholding a dynastic legacy. Do you think this kind of pressure is unique to the ultra-wealthy, or does it appear in other forms?

Dive into the book’s structure, characters, themes, and symbolism.

1. How does Monaghan develop the theme of The Burden of Caretaking through Dolly’s character arc? What key moments signal her shift from being the family’s sole “ringmaster” to someone capable of a true partnership?

2. What is the significance of the nautical term “the conn”? How does the term serve as a metaphor charting the evolution of Dolly and Stewart’s relationship?

3. How do the Whitfield acorns and Maud’s sewing machine represent two fundamentally different kinds of legacy? What do these contrasting inheritances reveal about Stewart’s and Dolly’s core values?

4. Stewart’s journey is one of redefining his priorities. In what ways do his interactions with Dolly and Gus challenge his work-focused worldview and allow him to discover a more authentic version of himself?

5. The narrative contrasts Dolly’s home on Goose Lane with the Whitfield estate. Beyond their physical differences, how do these two settings represent opposing ideas about family, community, and what it means to be home?

6. Why was Stewart’s public failure to defend Dolly at the Starlight Gala so important for both of their character developments? How did his choice to prioritize his legacy over their relationship in this scene set the stage for the novel’s resolution?

Encourage imaginative and creative connections to the book.

1. Dolly’s dream of opening a bakery finally comes true. If you were helping her design the menu, what signature baked good would you create for her, and what would you name it to reflect her story?

2. If Dolly All the Time were being adapted into a film, who would you cast in the lead roles of Dolly and Stewart? What qualities do those actors have that would bring these characters to life?

3. Imagine you’re writing a scene that takes place one year after the novel’s closing. What would a typical Saturday look like for the newly blended Brick and Whitfield family? What small, everyday moments would show how they have grown together?