Book Club Discussion Questions for The Most Beautiful Woman in Florence by Alyssa Palombo

1. What do you feel was Simonetta's strongest motivation for marrying Marco? Do you think she truly loved him, or did she only convince herself that she did? Could she realistically have refused to marry him?
2. Simonetta is sometimes frustrated by the effect that her beauty has on those around her, and at other times she uses it to her advantage. Did both of these reactions feel reasonable and realistic to you? How might you have felt in her situation?
3. Simonetta is widely proclaimed the most beautiful woman in Florence, and men wait outside her house, leave her gifts, and recognize her in the street. Do you see any similarities between the Florentines' reaction to Simonetta and our own celebrity culture today?
4. What do you think Marco hoped for in marrying Simonetta and bringing her to Florence? Do you think he got what he wanted?
5. Simonetta is a friend of both Lorenzo de' Medici and his wife, Clarice. How is her friendship with each of them different? How is it similar? What does she value about each friendship?
6. Simonetta feels as though, by posing for Botticelli, she becomes a partner in his creative work. Do you think he sees her that way as well? Why or why not? How do you see her participation in their artistic relationship?
7. At one point in the novel, Simonetta asks herself the following questions, only to realize she does not have the answers: "What is it about beauty which makes men think they have the right to desire you? That beauty means you automatically agree, somehow, to be coveted, to be desired? That your beauty belongs to everyone?" Do you think these questions are still relevant to the way in which our culture perceives beauty, especially female beauty? How are women who are considered beautiful still treated similarly to Simonetta? Where is the line between objectification and empowerment?
8. Simonetta refuses Giuliano de' Medici's advances and claims that she cannot violate her marriage vows. Yet she later does just that with Sandro. How did you feel about her decision? Did you feel she was justified?
9. In the last line of the book, as she is dying, Simonetta says, "Sandro promised me that I would live forever." Do you think she has, in fact, been immortalized? How do you think she would feel about the fact that The Birth of Venus is one of the world's most famous and beloved works of Western art?
10. Were you familiar with any of the works of art described in this novel before reading it? How did your familiarity (or lack thereof ) influence your reading of the novel? Did you look up any of the artwork as you read? Which were your favorites, and why?

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