1. In Chapter 1, why does Ben purchase two seats for himself on the airplane? Have you ever been in a social situation where you didn’t feel like interacting with other people? How did you handle it?
2. How would you describe Didi as a character? What are her strengths? What challenges does she face?
3. In Chapter 4, we meet both Lydia Richmond (Ben’s mother) and Thomm “Monte” Montgomery (Didi’s boss). How are these two characters similar? How are they different?
4. If you were required to choose, would you rather work for Lydia or Monte?
5. Why doesn’t Didi just quit working at DEI?
6. Why might some people remain in abusive situations or relationships when it’s clear to other people what’s going on?
7, In Chapter 16, Didi tells Ben this: “You stay at one place for so long, you begin to expect it to love you. You want it to notice the sacrifices you make and to say thank you on the difficult days. But it won’t. It can’t. It’s a place, not a person.” Have you ever worked at a place for too long? How did you know when it was time to leave?
8. What is Didi’s solution for when a place doesn’t love you back? Do you agree with it?
9. In Chapter 16, Didi shares her family’s story with Ben, specifically why her father is in jail. Ben reacts with this thought: “To dream and to fail was one thing. To be denied the chance to try was quite another.” Which do you think is more difficult to handle: dreaming and failing or never having the chance to pursue a dream in the first place?
10. Would you have accepted the job at Richmond Enterprises? Why or why not?
11. If you could ride the London Eye with one other person, who would it be and why?