Gather initial thoughts and broad opinions about the book.

1. The novel uses a “life review” narrative, a structure Matt Haig also explored in his bestseller The Midnight Library. If you’ve read both, how did Wilbur’s journey on the train compare to Nora’s experiences in the library? If you haven’t, what did you think of this premise as a way to explore a life full of regret?

2. How did the ending of the novel make you feel? Was Wilbur’s second chance in Venice a satisfying conclusion, or did you find it too convenient? What message do you think the ending conveys about redemption and the possibility of change?

3. What part of Wilbur’s journey on the Midnight Train was the most powerful or memorable for you? Was it a specific stop in his past, a conversation with a guide, or the final sacrifice he makes?

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

1. Wilbur’s journey forces him to re-examine key choices that shaped his life. Thinking about your own life, what moments do you see as major turning points? How did Wilbur’s story make you reflect on the relationship between small decisions and long-term consequences?

2. Maggie’s father advises Wilbur that “love is a garden” that needs constant tending (166). Thinking about the important connections in your own life, what does “tending” to them look like for you?

3. Wilbur’s ambition is portrayed as an “anesthetic” used to numb his grief. What is the difference between healthy ambition and the relentless “hustle culture” that consumes Wilbur? Have you ever felt a tension between your professional goals and your personal well-being?

4. The recurring motif of benches symbolizes the importance of quiet, present connection in the novel. Can you recall a time when a conversation in a similarly mundane setting made a major difference in your life?

5. On the train, Wilbur is returned to the age when he was “closest to his true self” (28). Can you think of a time when you felt the most authentic version of yourself, and have there been periods when you have strayed from your integral values?

6. Dougie’s secret gift of the stolen toy train completely changes Wilbur’s perception of his brother. Have you ever learned something about a person’s past that fundamentally changed how you saw them?

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

1. The novel critiques a modern “hustle culture” where professional achievement is often prioritized over personal well-being. Where do you see this pressure to relentlessly pursue success in our society today?

2. Wilbur’s desperate need to escape poverty is rooted in his childhood in post-war Britain. How does the novel illustrate the long-term psychological effects of growing up with scarcity and trauma? Do you see parallels in how economic hardship shapes individuals and communities today?

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

1. What is the effect of splitting the protagonist into two versions, the regretful Ghost and the innocent Dreamer? How does this dual perspective allow the author to explore themes of regret, potential, and self-forgiveness?

2. The motif of books and bookshops transforms dramatically throughout the story. How does their meaning evolve for Wilbur, and what does this transformation reveal about his character arc?

3. Agnes and Miss Graham offer Wilbur conflicting advice about his journey. What do their two opposing viewpoints represent? Which philosophy do you think the novel ultimately endorses?

4. How does the Sycamore Tree function as more than just a setting for a tragic event? In what ways does it become a symbol of Wilbur’s psychological state and his decades-long avoidance of his grief?

5. The Midnight Train follows a literary tradition of “life review” narratives, similar to Charles Dickens’s A Christmas Carol. What similarities and differences did you notice between Wilbur’s journey with Agnes and Scrooge’s visitations by the three spirits? How does Haig update this classic structure for a modern audience?

6. The friendship between Wilbur and Charlie is a moral compass in the novel. How does Charlie act as a foil to Wilbur? What does the eventual breakdown of their friendship signify about Wilbur’s transformation?

Encourage imaginative and creative connections to the book.

1. Imagine you could step onto the Midnight Train and have a conversation with the Dreamer just as his journey begins. What is one piece of advice you would give him to help him understand what he’s about to witness?

2. The novel ends with Wilbur and Maggie starting their life over. If you were to write an epilogue set 10 years later, what would their life look like? Would they have managed to hold onto the lessons Wilbur learned on the train?

3. If you were adapting The Midnight Train into a movie, what actors would you cast in the main roles of Wilbur (young and old), Maggie, and Dougie? What makes them the right fit for these characters?