Book Club Discussion Questions for Hello Beautiful by Ann Napolitano

1. Who is your favorite character in this book? Who did you most identify with, and why?
2. Discuss the rift that occurs between William, Julia, and Sylvie, and the choices each character makes to contribute to that rift. If you were involved in a similar situation, what might you have done?
3. How did the ending make you feel? What do you think might happen for William and Alice next?
4. Ann Napolitano has said that Hello Beautiful is an homage to Louisa May Alcott's Little Women. Have you read Little Women—and, if so, what traces of Alcott's classic novel of sisterhood do you see in Napolitano's?
5. Hello Beautiful is initially narrated from three perspectives: William's, Julia's, and Sylvie's. Why do you think the author chose these particular characters to tell the story? Whose voice did you enjoy or relate to the most? How did you feel when Alice's voice entered the story?
6. Discuss how mental health plays a role in the story of Hello Beautiful. Did William's depressive experience feel "real" to you, for example? What about his parents'?
7. Sylvie imagined her life to be full of "third doors," or unexpected ways of living that allow her to choose her own path. What third doors can you see in your own life? Have you ever wanted to make an unexpected decision? What did you choose?
8. Charlie described his daughter Julia as his "rocket"—an ambitious, independent woman who follows her own dreams. What about his other daughters: Do you think they fit that description as well, and how? What about Rose? You may take this opportunity to talk about the mother-daughter relationships in the novel as well.
9. Hello Beautiful highlighted a series of romantic partnerships: Charlie and Rose's, Julia and William's, Sylvie and William's, Emeline and Josie's. Which relationship do you think was the ideal in terms of love and connection, and why? Which were the most challenging?
10. In addition to romantic relationships, Hello Beautiful featured different types of nuclear families: William's; the Padavanos; Julia and Alice's; and the "super-duplex" where Cecelia, Izzy, Emeline, and Josie live together. Talk about what family looks like in the pages of this novel. Which family appeals to you most?
11. Discuss the character of Alice. In what ways was she like her mother? Her father? Sylvie, the aunt she doesn't remember?
12. While family was at the center of most of these characters' lives, friendships were also of great, life-affirming importance. Kent and Carrie, for example, were vital to William's and Alice's existence. What do you think friends add to our lives that families don't or can't? Do you have a best friend like Kent or Carrie?
13. The characters in Hello Beautiful keep secrets from each other, sometimes for years. Almost all of these secrets eventually come to light. Have you ever kept a secret from a loved one? Do you agree with the reasons why Emeline, Julia, and Rose kept secrets from theirs?
14. When Sylvie finds out that she has cancer, she worries more about William than herself. Why? Discuss their relationship, and the obstacles they faced. Would you make the same choices as Sylvie if you were in her position?
15. There are three mothers in Hello Beautiful: Rose, Julia, and Cecelia. Compare each of their parenting styles and decisions. Do you relate to one of them more than the others? Why or why not? What does a "good" mother look like in this novel?
16. Charlie is an imperfect father, but a beloved member of his community. Think about his relationships with his daughters—especially with Julia and Sylvie. How did his love help to shape them? In what ways was Charlie a "good" or a "bad" father?
17. Over the course of the novel, several of the characters experience tragedy and loss. What do you think the novel is saying about resilience and hope in the face of difficult times? And how, if at all, does this messaging speak to you?
18. William realizes that he never felt loved by his parents. He experiences one type of love from Julia, and another type of love from Sylvie. Talk about the different expressions of love in this novel. What do you think this novel is saying about what love really is?

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