This reading group guide for Tracy Flick Can’t Win includes an introduction, discussion questions, and ideas for enhancing your book club. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.

Introduction

Tracy Flick is back and, once again, the iconic protagonist of Tom Perrotta’s Election is determined to take high school politics by storm. Now in her forties, Tracy is a hardworking Assistant Principal at a public high school in suburban New Jersey. Feeling stuck and underappreciated in midlife, Tracy gets a jolt of good news when her school’s longtime Principal abruptly announces his retirement.

Excited by the opportunity to claim the top job, Tracy throws herself into her work with renewed zeal. At the same time, the hiring process triggers troubling memories about her own high school experiences, as well as her more recent personal and professional disappointments. As she broods on the past, Tracy becomes aware of storm clouds brewing in the present . . . Is she really a shoo-in for the Principal job? Is the Superintendent plotting against her? Why is the School Board President’s wife trying so hard to be her friend? And why can’t she ever get what she deserves?

Topics & Questions for Discussion

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?

Enhance Your Book Club

1. Curious about Tracy’s past? Read the Tom Perrotta’s novel Election to learn more about Tracy’s high school experience, which she grapples with in Tracy Flick Can’t Win.

2. Make your discussion of Tracy Flick Can’t Win into a book-to-screen night! Watch the cult classic movie adaptation of Election, starring Reese Witherspoon.

3. Looking for another satirical, compulsively readable novel set in high school? Pick up Curtis Sittenfeld’s Prep for your next book club meeting.