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Book Club Questions for Hello Beautiful by Ann Napolitano

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Book club questions for Hello Beautiful by Ann Napolitano explore the power of love and the lasting impact of our choices.

This is a beautiful story of love and the power of forgiveness. It teaches us about hope and the importance of being connected to one another no matter the distance.

For more context about the story, check out my spoiler-free review first.

Below you will find my discussion guide for this novel, as well as 20 original book club questions to keep your book club discussion flowing high. Also, don’t forget to read my book recommendations below the questions!

Summary | Characters

Book Review | Book Club Questions

About the Story

William Waters grew up in a house silenced by tragedy, where his parents could hardly bear to look at him, much less love him—so when he meets the spirited and ambitious Julia Padavano in his freshman year of college, it’s as if the world has lit up around him. With Julia comes her family, as she and her three sisters are inseparable: Sylvie, the family’s dreamer, is happiest with her nose in a book; Cecelia is a free-spirited artist; and Emeline patiently takes care of them all.

With the Padavanos, William experiences a newfound contentment; every moment in their house is filled with loving chaos. But then darkness from William’s past surfaces, jeopardizing not only Julia’s carefully orchestrated plans for their future, but the sisters’ unshakeable devotion to one another. The result is a catastrophic family rift that changes their lives for generations. Will the loyalty that once rooted them be strong enough to draw them back together when it matters most?

An exquisite homage to Louisa May Alcott’s timeless classic, Little Women, Hello Beautiful is a profoundly moving portrait of what is possible when we choose to love someone not in spite of who they are, but because of it.

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Book Club Questions for Hello Beautiful

I hope you will enjoy discussing my book club discussion questions for Hello Beautiful! Have fun analyzing the themes of the story with your book clubs, and let me know your thoughts!

1. Who is your favorite character in Hello Beautiful and why? What is it about their personality or experiences that drew you to them? How do they contribute to the overarching themes of the novel?

2. The rift that occurs between William, Julia, and Sylvie is the central conflict of the novel. What factors contributed to the breakdown of their relationships? How did their individual choices and actions impact the rift? In what ways did their family dynamics and past experiences play a role? If you were in their position, what alternative actions might you have taken to prevent or resolve the rift?

3. How did the ending of Hello Beautiful resonate with you? Did it provide a sense of closure or leave you with questions? What do you think might happen to William and Alice next, and why? How does the resolution of the novel reflect its larger themes of family, love, and forgiveness?

4. Ann Napolitano has drawn inspiration from Little Women to create Hello Beautiful. What similarities and differences do you see between the two novels? How does Napolitano’s novel build upon and subvert the themes of Alcott’s work? In what ways does Hello Beautiful speak to contemporary understandings of family and sisterhood?

5. The novel is narrated from multiple perspectives, including William’s, Julia’s, Sylvie’s, and Alice’s. Why do you think Napolitano chose these particular characters to tell the story? What unique insights do each of their perspectives bring to the narrative? Whose voice did you find the most compelling, and why? How does the inclusion of Alice’s voice shift the novel’s focus and themes?

6. Mental health is a significant theme throughout Hello Beautiful. How do the characters’ experiences with depression and anxiety impact their relationships and personal growth? How does the novel challenge common stereotypes and misconceptions surrounding mental health? In what ways do William’s parents’ own mental health struggles impact their ability to parent and form healthy relationships with their children?

7. Sylvie imagines her life as full of “third doors,” or unexpected opportunities and decisions that challenge societal expectations. What third doors have you encountered in your own life, and how have they impacted your personal growth? In what ways does Sylvie’s outlook on life challenge traditional notions of success and fulfillment? How do the other characters in the novel respond to Sylvie’s unconventional worldview?

8. Charlie’s daughter Julia was described as his “rocket,” an independent and ambitious woman who follows her dreams. Do you think that his other daughters, particularly Rose, share the same qualities? How do the mother-daughter relationships in the novel affect their ambitions and independence? Can you identify any factors that may have influenced each daughter’s personality and choices, such as their upbringing, family dynamics, or life experiences?

9. There are three mothers in HELLO BEAUTIFUL: Rose, Julia, and Cecelia. How do their parenting styles and decisions differ, and how do they affect their children’s upbringing and personalities? Do you relate to one of these mothers more than the others, and why or why not? Can you identify any factors that contribute to a “good” mother in this novel, such as unconditional love, support, or understanding?

10. When Sylvie learns she has cancer, she worries more about William than herself. What is the nature of their relationship, and what obstacles have they faced together? Can you identify any qualities that make their relationship particularly strong, such as mutual support, shared experiences, or affection? Would you make the same choices as Sylvie if you were in her position, and why or why not?

11. Secrets are a recurring theme in HELLO BEAUTIFUL, with many characters keeping them from loved ones for years. Eventually, most of these secrets come to light. Have you ever kept a secret from a loved one, and why did you do so? Do you agree with the reasons why Emeline, Julia, and Rose kept secrets from their family members, or do you think they should have been more forthcoming? How do these secrets affect the relationships between the characters, and can they be repaired?

12. While family plays a central role in the characters’ lives, friendships also provide significant support and affirmation. Kent and Carrie, for instance, are crucial to William’s and Alice’s well-being. In what ways do friends offer something different from families, and how do they complement each other? Can you identify any qualities that make a friendship particularly valuable, such as trust, loyalty, or shared experiences? Do you have a best friend who shares these qualities, and how have they impacted your life?

13. Alice is a character who shares similarities with her mother, father, and Sylvie, her aunt whom she doesn’t remember. In what ways do these similarities manifest themselves, and how do they affect her personality and choices? Can you identify any conflicts that arise from these similarities, such as Alice’s struggle to forge her own identity? How does Alice’s relationship with Sylvie compare to her relationship with her other family members?

14. The novel showcased various types of nuclear families, such as William’s family, the Padavanos, Julia and Alice’s family, and the “super-duplex” where Cecelia, Izzy, Emeline, and Josie lived together. How do these families differ in terms of structure, values, and dynamics? Which of these families do you find most appealing, and why? Can you identify any factors that contributed to their appeal, such as their closeness, supportiveness, or mutual understanding?

15. In HELLO BEAUTIFUL, several romantic relationships were featured, including Charlie and Rose’s, Julia and William’s, Sylvie and William’s, and Emeline and Josie’s. Which of these relationships do you think had the most ideal love and connection, and why? Were there any obstacles that challenged their relationship, such as differences in personality, values, or life goals? How did they overcome these obstacles, or did they fail to do so?

16. Charlie, the imperfect father in the novel, has a complicated relationship with his daughters, Julia and Sylvie. How did Charlie’s love for his daughters shape their personalities and life choices? In what ways did Charlie’s parenting style impact their decisions and future relationships? Do you think Charlie was ultimately a “good” or “bad” father? Why or why not? Consider the larger societal context and the expectations placed on fathers and daughters.

17. HELLO BEAUTIFUL deals with themes of tragedy and loss. As several characters face difficult times, what does the novel suggest about the human capacity for resilience and hope? How do different characters cope with grief and loss, and what are the consequences of their actions? How does this messaging about resilience and hope speak to you, personally, in your own life experiences?

18. In the novel, William experiences different types of love from different people. He feels unloved by his parents, but experiences a different kind of love from Julia and Sylvie. Discuss the different expressions of love in the novel and what they mean. How do these relationships shape the characters’ identities and life paths? What does the novel suggest about the nature of love and its role in our lives?

19. The narrative structure of the novel is unique, with alternating chapters between William and Julia’s perspectives. How did this structure affect your reading experience? Did you find it effective in creating tension and suspense?

20. William’s past is a significant part of the novel’s plot. Do you think he was justified in keeping it a secret from Julia? Would their relationship have been different if he had told her earlier?

21. The novel is set over several decades. How did the passage of time affect your reading experience? Did you find the historical backdrop of the story engaging?

22. The title of the book, HELLO BEAUTIFUL, is referenced several times throughout the novel. What do you think the title represents, and how does it relate to the story?

Selected Reviews for Hello Beautiful

“This sumptuous family saga is one of those rare novels whose singular characters are so beautifully rendered, it’s as if they’re your best friends, and you’re grateful to be in their orbit. Napolitano’s homage to Little Women, albeit set in late-20thcentury Chicago, will prompt you to slow down as you read, never wanting the book to end. When it does, prepare for tears.”Oprah Quarterly

“Radiant and brilliantly crafted . . . Napolitano’s [work] resists the easy satisfactions of the sentimental and never settles for simple answers to emotional predicaments faced by her characters.”—The New York Times Book Review

“A rich, complex family saga, Hello Beautiful is a portrait oflove and grief in equal measure. Napolitano’s prose is so lovely, so keenly perceptive, that it held me captive until I finished. A lot of people are going to love this story.”—Mary Beth Keane

Additional Recommendations

Hope you enjoyed my book club and discussion questions for Hello Beautiful by Ann Napolitano!

Here are some more of my book club recommendations:

Someone Else’s Shoes by Jojo Moyes

Who are you when you are forced to walk in someone else’s shoes?

Nisha Cantor lives the globetrotting life of the seriously wealthy, until her husband announces a divorce and cuts her off. Nisha is determined to hang onto her glamorous life. But in the meantime, she must scramble to cope–she doesn’t even have the shoes she was, until a moment ago, standing in.

That’s because Sam Kemp – in the bleakest point of her life – has accidentally taken Nisha’s gym bag. But Sam hardly has time to worry about a lost gym bag–she’s struggling to keep herself and her family afloat. When she tries on Nisha’s six-inch high Christian Louboutin red crocodile shoes, the resulting jolt of confidence that makes her realize something must change—and that thing is herself.

Full of Jojo Moyes’ signature humor, brilliant storytelling, and warmth, Someone Else’s Shoes is a story about how just one little thing can suddenly change everything.

The London Séance Society by Sarah Penner

From the author of the sensational bestseller The Lost Apothecary comes a spellbinding tale about two daring women who hunt for truth and justice in the perilous art of conjuring the dead.

1873. At an abandoned château on the outskirts of Paris, a dark séance is about to take place, led by acclaimed spiritualist Vaudeline D’Allaire. Known worldwide for her talent in conjuring the spirits of murder victims to ascertain the identities of the people who killed them, she is highly sought after by widows and investigators alike.

Lenna Wickes has come to Paris to find answers about her sister’s death, but to do so, she must embrace the unknown and overcome her own logic-driven bias against the occult. When Vaudeline is beckoned to England to solve a high-profile murder, Lenna accompanies her as an understudy. But as the women team up with the powerful men of London’s exclusive Séance Society to solve the mystery, they begin to suspect that they are not merely out to solve a crime, but perhaps entangled in one themselves…

I Have Some Questions for You by Rebecca Makkai

A successful film professor and podcaster, Bodie Kane is content to forget her past—the family tragedy that marred her adolescence, her four largely miserable years at a New Hampshire boarding school, and the murder of her former roommate, Thalia Keith, in the spring of their senior year. Though the circumstances surrounding Thalia’s death and the conviction of the school’s athletic trainer, Omar Evans, are hotly debated online, Bodie prefers—needs—to let sleeping dogs lie.

But when the Granby School invites her back to teach a course, Bodie is inexorably drawn to the case and its increasingly apparent flaws. In their rush to convict Omar, did the school and the police overlook other suspects? Is the real killer still out there? As she falls down the very rabbit hole she was so determined to avoid, Bodie begins to wonder if she wasn’t as much of an outsider at Granby as she’d thought—if, perhaps, back in 1995, she knew something that might have held the key to solving the case.

In I Have Some Questions for You, award-winning author Rebecca Makkai has crafted her most irresistible novel yet: a stirring investigation into collective memory and a deeply felt examination of one woman’s reckoning with her past, with a transfixing mystery at its heart. Timely, hypnotic, and populated with a cast of unforgettable characters, I Have Some Questions for You is at once a compulsive page-turner and a literary triumph.

Thank you for reading my book club discussion questions and as always, happy reading! ❤️