The Midnight Train discussion guide

By Gifted Bookworm

Wilbur is 81, newly widowed-in-spirit from a marriage that ended decades ago, and has just hung up the phone after a brief, bittersweet call with Maggie — the love of his life. Minutes later, he dies. What meets him next is a ghostly steam train and a guide named Agnes, who takes him on a single journey back through his own life. He can watch every choice that led him here. He just isn’t allowed to change any of it. Matt Haig’s companion novel to The Midnight Library is smaller in scale but just as tender: a book about regret, ambition, and the slow, ordinary ways we let love slip away.

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What’s inside (8 pages): cover sheet, welcome + content note, quick guide/characters/themes, meeting plan, spoiler-free questions, spoiler zone, mini activity (“Stops Along the Line”), ratings + next-month vote.

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Quick character cheat sheet

• Wilbur — our narrator; a Sheffield boy who becomes a bookshop-empire owner, and spends his whole life quietly haunted by what he lost.
• Maggie — the love of Wilbur’s life; sharp, artistic, and the emotional centre of the book even in her absence.
• Agnes Bagdale — the ghost of the woman who ran the Sheffield bookshop of Wilbur’s childhood; his guide on the train, and the keeper of its one unbreakable rule.
• Dougie — Wilbur’s older brother, whose recklessness and grief shape the whole family.
• Charlie Applewood — Wilbur’s oldest friend, eventually a casualty of Wilbur’s ambition.
• Edith — Wilbur’s mother, widowed young, whose grief hardens into resentment.

Themes to watch

Regret and the myth of the “one perfect moment” • ambition versus love • grief passed down through a family • fate versus free will • the cost of chasing security • nostalgia for the present, not just the past

This book touches on bereavement, wartime loss, miscarriage, and family estrangement. Please take care, and skip any questions your group doesn’t want to cover.

Discussion questions

Spoiler-free

1. Describe the book in three words — then compare answers.
2. Wilbur says his life “flashed before his eyes” as a slow train journey rather than a flash. Why do you think Haig chose that structure?
3. The book opens with Wilbur’s final phone call with Maggie. How did knowing where the story was heading change the way you read what came before?
4. Agnes tells Wilbur he can watch but not interfere. Did you find that rule frustrating, comforting, or both?
5. Wilbur’s family history — his father’s death, his mother’s resentment, Dougie’s path — shapes everything that follows. Which of those early scenes stayed with you most?
6. Wilbur chases wealth and security as a way of protecting himself from more loss. Where did you see that instinct pay off — and where did it clearly cost him?
7. What did you make of the bookshop as the thread running through Wilbur’s whole life?
8. Which supporting character (Dougie, Charlie, Edith, Agnes) mattered most to you — and why?
9. Compare this to The Midnight Library, if your group has read it. Does turning “what if” into “what was” change how the story hits you?
10. Who would you recommend this book to?

Spoiler zone

STOP HERE if anyone hasn’t finished the book.

1. Wilbur ultimately breaks Agnes’s rule and interferes with his own past. Did that choice feel earned, or did it let the story off the hook?
2. How did you feel about the way Wilbur and Maggie’s relationship unravelled — not through betrayal, but through Wilbur’s slow retreat into ambition?
3. What did you make of the ending — Wilbur waking back in Venice, young again, with the memory of the train intact?
4. Does the ending suggest Wilbur gets a genuine second chance, or is it something more ambiguous?
5. How does the novel’s take on regret differ from The Midnight Library‘s?
6. What do you think the book is ultimately arguing: that the past can be redeemed, or only understood?

Meeting plan (60–90 minutes)

• 0–10: Warm-up (3-word vibe / which moment in your own life would you want to revisit on the train?)
• 10–50: Spoiler-free discussion
• 50–70: Spoiler zone (optional)
• 70–80: Mini activity: Stops Along the Line
• 80–90: Ratings + vote for next month