1. Do you feel that Boylan had a choice in becoming a woman to the world?
2. What responsibility does Jenny have for Grace and their children? What responsibility do they have to her?
3. Have you ever known someone who made a gender transition? How did the change affect people who knew the person before?
4. How central a role do you believe gender plays in our identity? How much different and in what ways do you believe you'd be if you were a member of the opposite sex? Do you think that some traits are inherent in one gender?
5. Discuss Boylan’s experiences buying a car and buying a pair of jeans. Have you witnessed or experienced similar situations? Do you notice the differences in expectations and attitudes in the ways people of other sexes are portrayed?
6. What role does humor play in Boylan’s life and in this book?
7. The title of the book, “She’s Not There,” is the title of a song that Boylan sings. What do you think the title means in this case? Who is not there, and when?
8. What is revealed about Boylan in her friendship with Richard Russo?
9. As a teenager, Boylan believes that love will cure him from his feelings. In what ways is Boylan saved by love? In what ways do people usually expect to be saved by love? How often is it successful?
10. Discuss the concept of “normal” as it relates to Boylan’s narrative, and to your expectations.
11. On her web site, Boylan remarks, “As I look back at the story of my own life, I occasionally feel that being born transgendered was the best thing that could have happened to me. While dealing with this condition made life difficult for me, as well as for my family, it's also true that I have been given a rare gift in life, the gift of being able to see into the worlds of both men and women with clear eyes.” Do you feel that you know more about these worlds as a result of reading Boylan’s book?
12. Boylan says that her first awareness of being transgendered occurred when she was about three. What do you remember about your earliest sense of your identity? How often do you feel that what the world sees in you is at odds with what you know to be true?
13. After reading the book, did you identify with Boylan more or less than you had expected?