Book Club Discussion Questions and Guide for Tracy Flick Can't Win by Tom Perrotta

1. In chapter 1, while reflecting on the importance of her administrative work at Green Meadow High, Tracy Flick thinks: "It was easy to forget, when you were a grown-up and high school was safely in the past, how it felt to be a captive audience, the way time could stand still in a classroom, and one bad teacher could poison your entire life" (page 7). How does this idea—of the outsize impact high school experiences have on people's adult lives—echo throughout the book? Do you agree with Tracy's assessment? Name and discuss one example of an experience that has followed one of the adult characters into adulthood.
2. Whose idea is it to start the Hall of Fame? Consider what we know about this character and their previous career by the end of the novel; why might they have been drawn to the concept of a Hall of Fame?
3. When Tracy Flick first hears about Vito Falcone, she thinks, Ugh, I know that guy (page 52), even though she's never met him. What does she mean? What kind of guy does Tracy understand Vito to be, and why does she find this archetype frustrating?
4. Throughout the novel, Vito suffers from headaches, memory loss, and disorientation. What is causing Vito's symptoms? Consider the fact that the very thing Vito is famous for in Green Meadow—his track record in varsity football and his short career in the NFL—is causing him pain in his personal life. Why is this apparent contradiction meaningful to the story?
5. Tracy Flick struggles with negative self-talk. As she meditates (pages 98–99), she compulsively plays two phrases over in a loop, You failed, and You did the best you could, before realizing both are true. Why is coping with failure so difficult for Tracy? Where do her impossibly high expectations of herself come from?
6. Consider Jack and Alice Weede's relationship. What is the secret Jack has been keeping from his wife? After it is announced that Diane Blankenship will be inducted into the Hall of Fame, Alice reveals that she's known Jack's secret all along. Why do you think Alice had not confronted Jack previously?
7. In a conversation with Tracy, Marissa confides that Kyle has cheated on her previously, and that, while in her twenties, she once slept with a married man. In response, Tracy tells a secret of her own—that she had a relationship with a teacher when she was fifteen. Based on this conversation, what about her experience with Mr. Dexter do you think hurt Tracy the most?
8. Who is Reggie? Why doesn't the Selection Committee (other than Lily) consider Reggie to be a serious candidate for the Hall of Fame, even though he and Vito were both football stars at Green Meadow High? What role does race play in the difference between Vito's career and Reggie's?
9. Consider the rapport between Tracy and Lily. How does Lily's opinion of Tracy differ from that of some other students and faculty at Green Meadow High? How do Tracy's feelings about Lily differ from her feelings about her own daughter? What do you think accounts for the friendliness between them?
10. Who is Larry Holleran, and why was he being considered for the Principal job? In your opinion, what theme or idea does Larry represent in this novel?
11. Many of the adult characters—in particular Tracy, Kyle, and Vito—are ambitious and deeply concerned with succeeding, both personally and professionally. What does success mean to the characters in this book? What does this novel have to say about the limitations of success as a primary motivation? Which, if any, of the adult characters do you feel is truly happy, and why?
12. By the end of the novel, has Tracy achieved her goals? What does she have to endure to receive the recognition she sought at the beginning of the novel? In your opinion, has Tracy "won"? Why, or why not?

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