Book Club Discussion Questions and Guide for When We Were Bright and Beautiful by Jillian Medoff

1. What was your reaction to the first line of the novel: "This is Billy's story, but if I were the one telling it, I'd start with Nate's call"? As you read further, did your understanding of Cassie's statement change?
2. How would you characterize Cassie's relationship with her brothers, Billy and Nate? Do you have siblings, and if so, how would you react to the news that one of them had committed an act of violence?
3. How did Cassie being an outsider of sorts to the Quinn family bear on her relationship with them and perceptions of them?
4. Cassie says, "Money is a noose that binds parents and children together in ways you can't anticipate." What does she mean? How does having money (or, conversely, not having money) complicate relationships among family members? Between lovers?
5. Is Cassie a reliable narrator? If not, what might her unreliability stem from?
6. Do you think it's possible to heal from traumas that take place in childhood and early adulthood? What steps might one need to take?
7. Did your initial reaction to Detective Haggerty change as you learned more about him? What about the Quinns' lawyer, Peter DeFiore? Is he morally clear-cut or ambiguous? If he felt Billy were guilty, would it be moral of him to represent him?
8. Cassie uses the phrase "I knew, and I didn't know" a few times over the course of the novel. What do you make of this phrase? Can you know something on a subconscious level but not know it consciously?
9. Is Eleanor's apology toward the end of the book merited? Do you think she is being sincere?
10. What is the significance of the last paragraph of the book for you? Do you think Cassie's telling of this story will change as she gets older?

Unless otherwise stated, this discussion guide is reprinted with the permission of Harper. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.