Book Club Discussion Questions and Guide for Cleavage by Jennifer Finney Boylan

1. Jenny describes this book as a "bookend" to She's Not There, her 2003 memoir. Did you read that earlier book? What has changed for Jenny, and what has remained the same?
2. In the chapter titled "Food," Jenny describes the way transition has altered her relationship to cooking, eating, and — most of all — her own body image. Do the women you know struggle with these issues in a different way than the men you know? In what way are these struggles different?
3. In the chapter titled "Voice," Jenny talks about the desire to fit in, to "pass" as female undetected. Have you ever wanted to fit in so badly with other people that you lost part of yourself? What is gained and what is lost when we fit into a new group?
4. Were you surprised at Jenny's reaction when Zai came out? How would you react if your own child — or someone else you loved — came out as trans?
5. In "The Heisenberg Variations" chapter, Jenny seems to suggest that the processes we go through to reinvent ourselves is similar, if not identical, to what's involved when writers revise their work on the page? Have you ever tried to write your own story? Is it harder to revise than to invent?
6. In describing her friendships, Jenny seems to have decidedly different relationships with her male friends than with women. Are your friendships different depending on the sex of your friend? Would your friendship remain the same if they changed genders?
7. What role do you think Jenny's sense of humor plays in her ability to survive and adapt?
8. Did you know a lot about the lives of transgender people before you read Cleavage? If not, how has your opinion changed after reading the book?
9. Jenny describes the word "cleavage" as a contronym — that is, a word that means its own opposite. Do you think men and women are "opposites"? What opposites, or contradictions, do you think you contain?
10. One of the questions Jenny wrestles with is whether or not she is "the same person" before and after transition. Do you think you'd be the same person if you changed genders? What about you would change, besides the physical?
11. In the chapter "Shadows," Jenny confronts the danger that she finds herself in, and that women sometimes find themselves in, in this world. If you are a woman, have you ever felt unsafe? Do you think men properly understand the sense of danger that women sometimes face?
12. Jenny's wife, Deedie, seems to love her wife for who she is, not for whatever body she is packaged in. If the person you loved changed genders, would you be able to stay with them? Do you think Deedie is exceptional? Or is she simply doing what lovers do, when their loved one is in trouble?

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