1. Valentine Roncalli begins her tale with the words, "I am not the pretty sister. I'm not the smart sister either. I am the funny one." How does her outlook color her actions? What do you think of Valentine? Do you agree with her assessment or do you think she might be selling herself short?
2. One of the major themes of Very Valentine is family. Describe the Roncalli family. How does their bond enrich Valentine's life? How might it affect her adversely, both in her romantic and professional endeavors? Offer some examples from the novel.
3. What defines family for the Roncallis? How would you fit into Valentine's family? What defines family for you? What is your family life like now and what were your experiences growing up?
4. Compare Valentine with her mother, Michelina ("Mike"), and her grandmother, Teodora. What elements of her personality does Valentine get from both women? Does she take after one more than the other?
5. Valentine's sister-in-law, Pam, has a difficult time fitting into the Roncalli family. How much of this is the result of her own actions? Are the Roncalli sisters responsible as well?
6. Tradition is another them of Very Valentine. Her sister Tess calls Valentine traditional, yet Valentine disagrees. "I guess I appear to be one of my tribe, but the truth is, whenever I have the opportunity to walk the hard line of tradition, I balk." Is Tess right, does Valentine represent tradition? How does she balk at it, as she claims? Which sister has the more realistic view?
7. Valentine ponders the question: "How do we survive in a contemporary world without losing everything my great-grandfather built?" Is there a role for tradition and traditional craftsmen and artisans in our technologically dependent modern world?
8. What does tradition mean for your life? Are there any you particularly cherish that have been handed down through past generations? How do you keep traditions alive? How can you start new ones?
9. Romantic love and the yearning for it infuse the novel. Valentine is a single woman in a world seemingly defined by marriage. Can a woman be fulfilled and yet remain single? Can she be happy without a man?
10. Describe Valentine's love interests, Roman and Gianluca. What does each man provide that the other doesn't? Did you prefer one to the other? Do you think she could be happy with either of them—or someone like either of them?
11. When Roman tells her that he will be few days late meeting her in Capri, what do you think about her reaction to his news? What about when he cancels on her?
12. What role did the trip to Capri play in Valentine and Roman's relationship?
13. The Roncalli family offers numerous insights, both profound and humorous for Valentine. Her mother tells, "You see, that's when you know for sure somebody loves you. They figure out what you need and they give it to you—without you asking." What do you think of this view of love?
14. Mike also advises her daughter, "I believe in setting goals that one can achieve. Low expectations make for a happy life." Can not expecting much make you happy? How? What would happen to Valentine if she followed this advice?
15. When talking to her father, Valentine discovers that he has a spiritual philosophy: "What about me is eternal?" How would you answer this question? Besides children, what might you leave to future generations?
16. Throughout the novel, Valentine works hard to save the Angelini Shoe Company. If she is successful, she gains stability. What do you think will happen if she fails?
17. Valentine describes the art of making shoes: "My grandmother has taught me that the palette for leather and suede is limitless, like musical notes." What do our shoes say about ourselves? How is Valentine's passion, making shoes, a metaphor for her life?
18. In Adriana Trigiani's vivid prose, New York City and Italy are like "characters" in the book. Describe Valentine's New York. How does "her" city compare to the New York you might know of—or have imagined? What is Italy like through her eyes? What does each place offer Valentine?
19. What does Valentine learn about herself in Italy? How do those lessons affect her?
20. What do you think of Teodora's news? Why do you think she kept her relationship a secret all those years?
21. At the end of the novel, Valentine turns away from both Roman and Gianluca. "In this moment, I choose art." Is this the right choice for her? What might it mean for her and for the Angelini Shoe Company? Does she have to choose love and career?
23. What did you learn from Valentine's experiences? What advice would you give her about her love life and her career?
(Questions isssued by publisher.)
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