Book Club Discussion Questions for Cruel Beautiful World by Caroline Leavitt

1. Why do you think Leavitt called this novel Cruel Beautiful World? How does the title relate to the themes of her novel?
2. Leavitt's novel is told from the points of view of five characters: Charlotte, Lucy, Iris, Patrick, and William. Do you think the novel is more effective told this way, from a closed point of view, or do you think it would have had more impact if she had used a third-person omniscient narrative? Why do you think Leavitt chose this way of telling the story, and how would the novel have been different if she had taken a different approach?
3. Leavitt is deliberately unclear about what really happened to Lucy and if William was really culpable.  Why do you think she left it open-ended? What do you think really happened—and why?
4. How does the time period in which the novel is set, the late '60s and early '70s, lend itself to the themes that appear in Cruel Beautiful World, especially in terms of love, family, and a rapidly changing era? If the story were set in contemporary times, how do you think it would it differ?
5. In her novel, Leavitt investigates family, what it means to be part of one, and what it means to bend the rules about what "family" can really mean. Which of the families in Cruel Beautiful World seem to be the most successful, and why? What do you think Leavitt is saying about the nature and importance of family?
6. An underlining theme of Cruel Beautiful World is about how we can control some things and prevent others, but sometimes simply yield to life and let it happen. Do you agree with the author's position? Why or why not?
7. There are so many "what ifs" in Cruel Beautiful World, and characters seem to constantly wonder how life might have been if things had been different. Given the situations the characters find themselves in, do you think they could have made different decisions that would have changed the outcome, or would everything have had to play out just as it did? Do some of the characters seem to feel trapped by their circumstances? If so, which ones, and do you think they could have done more to effect change in their lives?
8. The shadow of Charles Manson and his "family" seems to provide a kind of backdrop to the book. Why is Lucy so affected by the distant characters?  Do you feel that she is similar to those in the Manson family? Why do you think the fascination with these young women continues to this day?
9. Leavitt writes about many different kinds of love, and as one early reviewer of Cruel Beautiful World stated, the novel "is all about love until it's not." What do you think this reviewer meant? In writing about the many faces of love, what statement do you think the author is making about love in general?
10. Leavitt has said in interviews that she likes to have what she calls "never-ending story" endings, where nothing is neatly tied up, and the reader is left to wonder what is going to happen next. Did you feel the ending of Cruel Beautiful World was satisfying? What do you imagine will happen next in the lives of these characters? What questions for you were unanswered?

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