1. Why does Hillary feel injured when Carly Simon refers to her as a "fan," and what do her efforts to connect with Simon and the singer Carole King suggest about her own ambitions in life?

2. In what ways does the unusual format of Queen of the Oddballs (memoir interspersed with timelines, diary entries, screenplay excerpts, photos, etc.) enable you to appreciate the diversity of Hillary's life experiences?

3. How do Hillary's fellow teenage activists succeed in helping her come to terms with her low self-esteem about her body?

4. In what respects is Hillary's success on The Gong Show significant in terms of her personal growth?

5. How does Hillary's series of failed romances reflect her own emotional insecurities, and to what extent does her relationship with Maxine mark a personal transformation?

6. "Pick a character -- any persona -- who is imbued with traits you desire." Why does Hillary feel the need to assume alter egos that differ so dramatically from her own identity?

7. To what extent do you agree with Hillary's therapist that she is attracted to "darkness" in her personal relationships? How does this darkness color Hillary's sense of humor and perspective on life?

8. How does Hillary's experience on Oprah! reveal her own conflicted feelings about being a performer and her preference for lurking behind the scenes?

9. Of all of Hillary's encounters with celebrities and Hollywood figures, which did you find most entertaining and why?

10. Have you ever felt like an outsider, or done something out of the ordinary, or a bit odd? Does Hillary's approach to living a life unaccording to plan have any effect on how you view your life or yourself?