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About The Book

Soon to be a major motion picture starring Reese Witherspoon

“Tom Perrotta is…one of the great writers that we have today. I love this book.” —Harlan Coben

An “engrossing and mordantly funny” (People) novel about ambition, coming-of-age in adulthood, and never really leaving high school politics behind—featuring New York Times bestselling author Tom Perrotta’s most iconic character of all time.

Tracy Flick is a hardworking assistant principal at a public high school in suburban New Jersey. Still ambitious but feeling a little stuck and underappreciated in midlife, Tracy gets a jolt of good news when the longtime principal, Jack Weede, abruptly announces his retirement, creating a rare opportunity for Tracy to ascend to the top job.

Energized by the prospect of her long-overdue promotion, Tracy throws herself into her work with renewed zeal, determined to prove her worth to the students, faculty, and School Board, while also managing her personal life—a ten-year-old daughter, a needy doctor boyfriend, and a burgeoning meditation practice.

But nothing ever comes easily to Tracy Flick, no matter how diligent or qualified she happens to be. Her male colleagues’ determination to honor Vito Falcone—a star quarterback of dubious character who had a brief, undistinguished career in the NFL—triggers memories for Tracy and leads her to reflect on the trajectory of her own life. As she considers 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?

A sharp, darkly comic, and pitch-perfect chronicle of the second act of one of the most memorable characters of our time, Tracy Flick Can’t Win “delivers acerbic insight about frustrated ambition” (Esquire).

Reading Group Guide

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.


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.

About The Author

© Beowulf Sheehan

Tom Perrotta is the bestselling author of ten works of fiction, including Election and Little Children, both of which were made into critically acclaimed movies, and The Leftovers and Mrs. Fletcher, which were both adapted into HBO series. He lives outside Boston.

Product Details

  • Publisher: Scribner (June 7, 2022)
  • Length: 272 pages
  • ISBN13: 9781501144080

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Raves and Reviews

"Perrotta has what it takes to revisit the past without being predictable.”—The Atlantic

“Perrotta . . . tells the story through a web of different characters and perspectives. It’s a book populated with middle-aged people disappointed in what life has brought—and yet, Tracy Flick Can’t Win is an oddly uplifting read. Perrotta’s great gift is that he lets his love for his characters, flaws and all, shine through, and Tracy emerges as a much richer, more sympathetic character than in the earlier book; she has grown, as has her creator. . . . I was rooting hard for Tracy Flick to, finally, win.” —Seattle Times

“This sequel, set in 2017, takes a sympathetic view of now middle-aged Tracy, an assistant principal and single mom, as she reconciles her past ambitions with her current dissatisfaction in life. Perrotta brings his trademark dark humor and insights into suburbia to the story, along with some sweet observations about friendship.”—Real Simple

"The heroine of Perrotta’s Election returns in this sharp and perfectly executed story of frustrated ambition…This is the rare sequel that lives up to the original.”Publishers Weekly, starred review

"In this culturally savvy sequel to his enduring best-seller, Election (1998), and its wildly popular film adaptation starring Reese Witherspoon, Perrotta again tells a smart, entertaining story from multiple perspectives, oral-history style. The breeziness of the pacing provides tart counterpoint to weightier themes of adultery, ambition, atonement, and revenge which Perrotta handles with a deft but determined satiric touch.”Booklist

“Combining narrated chapters with short first-person “testimonies” by five of the characters, the plot unfolds with the you-are-there feel of a documentary, or mockumentary perhaps ... the ending is a shocker. Nobody told this master of dark comedy there are things you can’t make jokes about. Watch him try.”Kirkus

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