Book Club Discussion Questions
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For supplemental discussion material see our Beyond the Book article, Willa Cather and the American Outsider Experience and our BookBrowse Review of Win Me Something.
Please be aware that this discussion guide will contain spoilers!
- Win Me Something is a searching book. In your opinion, what is Willa looking for?
- Food plays an important role in terms of comfort, identity, connection, and more. Discuss how the author uses food in both communal and personal ways.
- Win Me Something flashes back in time to Willa's childhood. Why do you think the author made the decision to show Willa's upbringing?
- Flowers are a recurring image—what might be their significance?
- Throughout the novel, racism and prejudice are pervading themes. How do they manifest overtly in scenes and also in subtext?
- New York and New Jersey are both important settings—what parts of each do we see, and why do you think we are shown certain locations?
- Mothers play critical roles in Win Me Something. How are the mothers in this novel portrayed and to what end?
- At one point, Willa thinks, "I wanted to be chosen, or to choose—maybe I wasn't sure the difference yet. Just that I saw choices glimmering outside my reach, and I wanted to get closer." Have you ever felt the way she feels here? By the book's end, does Willa get what she wants?
- Ethan's arrival to the Adriens' home can be seen as a turning point in the novel. Does he change the dynamic or reveal something that was already there?
- Toward the end of the book, Willa says that she wishes someone would tell her what she's experienced was "real." What do you think she means by this?
- What do you think the title, Win Me Something, means for Willa?
Unless otherwise stated, this discussion guide is reprinted with the permission of Tin House Books.
Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.
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