Discussion Questions

1. Ana is the definition of driven, always striving toward perfection. In what ways is this a good quality? How is it harmful? How important is it to you to “check the boxes” in your own life, literally or figuratively?
2. Bryan compares himself to the Prodigal Son of the Bible story (see Luke 15:11-32), wondering what happened when the Prodigal had to prove he was a changed man. How do you imagine the rest of the Prodigal’s life played out? Have you encountered people who cling to an old perception of you? Were you able to persuade them that you’d changed?
3. Through the outward symbols of her success —her wardrobe, her car, her apartment —Ana carefully crafts the image she presents to the world. Bryan is also accused of hiding his true self behind his reputation as a shallow playboy. What “armor” do you wear when you want to protect yourself or project a certain image? Do you struggle, as Ana does, to let others see your vulnerabilities?
4. For a long time, Ana and Bryan resisted their attraction to each other, in part because of their interconnected friend group. Were they wise to do so?
5. Though she’s mostly satisfied with her life, at times Ana feels left out and lonely once her two best friends begin working together and find romantic relationships. Have you ever felt like the odd one out in a group of friends? What happened?
6. Bryan and Ana both experience major disruptions to the careers they’ve built over many years. Have you ever had a sudden change to your life’s direction? If you found yourself with the chance to start over and do something new, what would you choose?
7. Ana is great at her job, but sometimes bothered by the work she does to protect or spin clients’ images. Do you think she’s right to feel that way? How would you advise her if she came to you with her concerns?
8. Bryan never feels like the son his father wanted, so he gives up on the idea of pleasing him. Ana also fears she can’t meet her family’s expectations, but she tries by doing things like continuing to attend Mass. Do any parts of your life look different from what your parents might have wanted or expected? Which character’s response do you most relate to?
9. Ana keeps a huge secret from everyone, including Bryan and her best friends. Did you understand her reasons?
10. As Bryan faces a crisis, Mitchell tells him, “Don’t be so quick to fix a situation that might not be yours to fix.” What do you think of this advice? When have you tried to fix something that might not have been your responsibility? What was the result?
11. Ana, Melody, and Rachel all face big changes as the story ends. What do you think the future holds for their friendship? Who are the longest-running friends in your life, and what kind of changes have you endured together?