The Midnight Train

1. Wilbur loved Maggie deeply but prioritized his ambition and daily life over that love. Do you think he realized this at the time or only in hindsight? Does that make him more or less sympathetic to you?

2. We mainly see Maggie through Wilbur's perspective, making her feel more like his loss than a fully realized character. Did you feel you got to know her as a person?

3. Wilbur often reflects on his honeymoon in Venice, comparing everything to that time. Is he idealizing the past, or was their relationship truly amazing? If it's idealization, what does that reveal about what he's missing?

4. Dougie's death leaves a mark on Wilbur that never fully heals. Do you think Wilbur ever really got over his death - or did he bury it and keep moving? And how much do you think losing Dougie shaped the man Wilbur became, including the choices he made with Maggie?

5. After losing her husband in the war, Edith viewed Wilbur and Dougie as burdens. How do you think this perception affected Wilbur in adulthood and his relationships? Do you feel sympathy for Edith, or is it too hard to forgive her for what she took from them?

6. Wilbur had a really hard childhood; building something big probably felt like proof that he'd made it out. Do you think he ever really chose success over happiness, or did he keep telling himself he'd slow down eventually - the way so many of us do - until one day it was simply too late?

7. The honeymoon is a cherished memory for Wilbur, seen as the best time in his life. But was Venice truly perfect, or the last moment before everything changed? Is he mourning Maggie, or longing for the version of himself he was back in Venice?

8. Miss Graham introduced Wilbur to books and a broader world. He built an empire around them, but his passion shifted to ambition. Did he honor her influence for the right reasons?

9. Agnes enforces the rules, keeping Wilbur in check. Did you trust Agnes as Wilbur did? What do you think Haig meant by having her be someone from Wilbur's life instead of a stranger?

10. Wilbur witnesses his life instead of rewriting it, yet he breaks the rules. Was he wrong to do so? What does it say about him that he would trade eternity for a chance to fix his mistakes? Is this the book's most romantic act or its most reckless?

11. In the end, Wilbur and Maggie get a second chance. Did it seem right to you, or was there something bittersweet underneath it, knowing what it cost to get there?