What Happens in Paradise

Gather initial thoughts and broad opinions about the book.

1. What were your initial feelings about the book as a follow-up to Winter in Paradise? Does this novel work as a standalone read, or does it need the context of the first book in the series?

2. Hilderbrand is celebrated for her novels set in her hometown of Nantucket, Massachusetts. If you’ve read her other works, such as The Five Star Weekend or The Hotel Nantucket, how did What Happens in Paradise compare?

3. Ayers finds herself caught between the familiar but untrustworthy Mick and the new, exciting, but complicated Baker. What factors do you think drive her decisions in this romantic triangle? Which relationship, if any, did you find yourself rooting for?

4. This story is the second installment in a trilogy. Did the ending make you want to keep reading the third novel in the series?

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

1. The Steele brothers move to St. John, hoping to find new beginnings in the wake of their personal crises. Have you ever dreamed of starting fresh in a new place to solve personal or professional challenges?

2. Irene’s discovery of Russ’s secret life forces her to reexamine her identity as a wife. Think about a time in your life when a major event forced you to see yourself or your relationships in a completely new light. How did you navigate that shift in perspective?

3. Ayers becomes the keeper of Rosie’s secrets when she finds the journals, which complicates her loyalty and understanding of her friend. Have you ever been entrusted with a friend’s secret that changed how you saw them? How did you handle that responsibility?

4. Huck’s decision to offer Irene a job is sparked by a brief conversation with a charter client about second chances. Has a piece of advice or an observation from an unexpected source ever prompted you to make a significant life change?

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

1. The novel’s mystery is rooted in white-collar crime, involving a hedge fund and offshore bank accounts to launder money. How does the story’s portrayal of high-stakes financial fraud reflect real-world issues of wealth, corruption, and accountability?

2. Hilderbrand mentions that the St. John in the novel is a pre-hurricane version of the island. How does knowing about the real-life devastation caused by Hurricanes Irma and Maria in 2017 influence your reading of St. John as an idyllic, yet vulnerable, paradise?

3. Cash’s evolving relationship with Maia highlights Hilderbrand’s exploration of non-traditional family relationships. How does the novel’s depiction of these unconventional family dynamics contribute to its broader exploration of how families are formed and redefined?

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

1. How does the author’s decision to alternate between multiple characters’ perspectives, alongside Rosie’s journal entries from the past, shape your understanding of the truth? What effect does this structural choice have on the narrative suspense?

2. What do you consider the most pivotal moment in Irene’s transformation from a grieving, passive wife to a resilient, independent woman? What does her journey suggest about The Challenges of Choosing to Love Again After Heartbreak?

3. The narrative explicitly names Todd Croft’s yacht Bluebeard, alluding to the dark French folktale of a pirate who murdered his wives. How does this specific literary reference deepen your understanding of the danger and moral corruption hidden beneath the surface of Russ’s secret life?

4. In what ways does St. John’s small, interconnected community function narratively? How do the island’s gossip networks and the fact that “everybody knows everybody” help to advance the plot and complicate the characters’ attempts to keep secrets?

5. Which character or situation do you think best exemplifies The Tension Between Objective Fact and Emotional Reality? What does their arc reveal about the subjectivity of truth?

Encourage imaginative and creative connections to the book.

1. Design a memorial for Rosie on St. John that captures the complexity of her life. What form would it take, where on the island would it be located, and what elements would you include to honor both the woman her friends knew and the secrets she kept?

2. Step into the shoes of FBI Agent Vasco for a moment. Write a brief, confidential memo to her superior summarizing her impressions of Irene Steele after seizing the villa. What would she note about Irene’s character, demeanor, and potential knowledge of the crimes?

3. Picture yourself as an editor at Heartland Home and Style magazine. What kind of feature story would you pitch about Irene’s beautifully restored Victorian home in Iowa City after the FBI seizes it? What would the headline be, knowing the secret and tragic story that unfolded within its walls?