Road Trip

Gather initial thoughts and broad opinions about the book.

1. How did the novel’s blend of family drama, historical mystery, and romance work for you? Which of these elements did you find most compelling, and why?

2. This story is built around a road trip that becomes a journey of self-discovery. How effective did you find this structure for exploring the sisters’ relationship and uncovering family secrets? Can you compare it to other famous journey narratives you know, and what sets this one apart?

3. Let’s talk about the ending. Did the neat resolutions for both Maeve and Therese feel satisfying to you? How did you feel about the revelations in the epilogue, and did they feel earned after the turmoil of the main story?

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

1. The sisters begin the novel with very defined roles, Maeve as the responsible caregiver and Therese as the unreliable free spirit. Have you ever felt locked into a specific role within your own family or friendships? 

2. The stories that Mary Helen tells her daughters about the portrait prove vital to the plot. Share a story from your family. How has this story influenced you? 

3. One of the novel’s major themes is Embracing Risk Over Certainty. Think about a time in your life when you had to choose between a secure, predictable path and a more uncertain one. What factors influenced your decision?

4. The savings in Mary Helen’s coffee can make the trip possible. If you were given a can of cash with the instruction to take a trip, where would you want to go and with whom? What do you think that trip would accomplish for you?

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

1. The novel tackles the issue of elder financial abuse through Mary Helen’s manipulation by the televangelist Brother Jerome. How effectively do you think the book portrayed the vulnerability of seniors to these kinds of schemes? What does this subplot reveal about the intersection of faith, trust, and exploitation?

2. The 1974 IRA art heist at Tarrymore is based on a real historical event. How does the novel use the political turmoil of “the Troubles” as a backdrop for Esme’s personal rebellion and the Rossington family’s secrets? What does it suggest about how large-scale political conflicts can impact individual lives?

3. What did Kathleen’s journey to America and her processing at Ellis Island reveal to you about the immigrant experience during that era? How does her story of hardship and resilience connect to broader narratives of Irish-American identity?

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

1. In what ways does the historical narrative deepen your understanding of the contemporary one? How does knowing Kathleen’s truth from the beginning create dramatic irony as Maeve and Therese conduct their investigation?

2. Maeve and Therese are presented as classic foils, with Maeve being logical and cautious while Therese is impulsive and intuitive. How do their contrasting approaches to problem-solving work together to unravel the mystery? At what points in the story is one sister’s method more effective than the other’s?

3. How did reading Kathleen’s story in her own words affect your connection to her as a character? What power do these letters hold that a simple third-person account of the past might not have conveyed?

4. How does the novel’s depiction of Kathleen’s journey compare to other portrayals of early 20th-century transatlantic voyages you might be familiar with, such as the film Titanic? What aspects of her experience felt particularly authentic or eye-opening?

5. How does the Tarrymore estate function as more than just a setting? In what ways does the physical state of the property reflect the emotional and moral state of the Rossington family line?

Encourage imaginative and creative connections to the book.

1. If you were adapting Road Trip into a movie or a limited series, which character’s perspective would you center the story on? Would you stick with the dual timeline, or would you tell the story in a different way to build suspense for the screen?

2. Maeve decides to write a historical novel about Kathleen’s life. What scene from Kathleen’s story, either one we read in her letters or one we can imagine, do you think would make the most powerful opening chapter for Maeve’s book? What would you title the novel?