This readers group guide for The Optimist’s Guide to Letting Go 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

Three women grapple with a life-changing secret in this mother-daughter generational story.

Owner of gourmet food truck Grilled G’s and recent widow Gina Zoberski finds comfort cooking up deliciously inventive grilled cheeses for her customers as she struggles through each day, especially when challenged by her critical mother, Lorraine, and her moody daughter, May.

Lorraine expects her family to live up to her high expectations, making sure to appear perfect to the public eye. May is mourning her father and wants nothing more than to do so in her own way. Gina is the perpetual optimist, always aiming to please, but is finding that the brighter side of things is not always so bright.

When Lorraine suffers an unexpected stroke, Gina discovers a family secret that Lorraine has kept hidden for forty years. As her mother’s health fails and her daughter rebels, Gina might find that piecing together the truth may just be the push she needs to let go. . . .

Topics and Questions for Discussion

1. The Optimist’s Guide to Letting Go opens with a quote from Anita Diamant’s The Red Tent: “The more a daughter knows about the details of her mother’s life—without flinching or whining—the stronger the daughter.” Discuss the quote’s significance. How does it set the tone for the novel?

2. Gina describes her husband, Drew, as the rock of the family. After he died, Gina and May completely disconnected. “Without him, she and May tumbled through each day, flailing in the rushing waters, occasionally bumping into each other” (p.15). Why is Gina and May’s relationship suffering, rather than getting stronger, in the wake of their shared loss? Is either of them at fault for failing to console each other through their grief? How can their bond be mended?

3. How would you characterize Lorraine’s role in her daughters’ lives? Why is she such a source of irritation rather than encouragement, especially to Gina? What are Lorraine’s guiding principles in life? How would you react to Lorraine’s criticisms if you were Gina?

4. Lorraine justifies her decision to keep Joe a secret from her daughters. “Telling the girls wouldn’t change anything in their lives; it would only create an abyss where their perfect family once stood. They didn't need to know what they had lost when they had never even known it existed. You couldn’t miss someone you’d never known” (p. 65–66). What do you think? Should Lorraine have told the truth to Gina and Vicky sooner? How would their lives be different? Is it possible to miss someone you’ve never known?

5. Gina’s family often gives her a hard time for her positive attitude. Can being an optimist ever be a negative? How does Gina’s uplifting disposition give her strength? What does she need to let go of, as the book’s title suggests?

6. Lorraine and Floyd’s marriage transpired out of convenience and security rather than love and admiration. Describe how their union is complex. How do they each benefit from their partnership? Do you understand their reasons for being together? Can a marriage that was established as a business proposal be successful? What does being married mean to you?

7. Discuss the structure of the novel. How does the movement from past to present impact your understanding of Lorraine, Gina, and May? How important is it as a reader to learn of a character’s history? How does each woman’s past shape her present relationships?

8. Gina is frustrated by Vicky’s insinuations that she should start dating. “What all of these people didn’t understand is she couldn’t fast-forward her grief. It wasn’t another item on her checklist she could accomplish then cross out” (p.116). Do you think Vicky is being insensitive to Gina’s situation? How will Gina know when she’s ready to move on? Is there an expected time line for grief?

9. Roza is Lorraine’s closest and most treasured confidant. “Roza was a time capsule of all Lorraine’s best and worst moments, and she had always been there when Lorraine needed her” (p.127). Do you think Roza filled the void left by Joe? How is she a source of comfort for Lorraine? What does their relationship teach you about the endurance of female friendship?

10. What do you make of Vicky’s relationships with Gina and Lorraine? Describe her role in the family. Why do you think the author chose not to have any chapters told from Vicky’s perspective? Would you have liked to learn more about her marital issues, or be given more insight into her adolescence? How would that have changed the novel?

11. Many of the characters in the novel choose to conceal their pain, love, or even their identity. Floyd’s sexuality, Gina’s heartache, and Lorraine’s first marriage are all buried secrets. Why do you think these characters choose to disguise their truths? How are these secrets burdening themselves and their families?

12. There are many parallels in Lorraine and Gina’s lives. They both fell in love with men whom their parents disapproved of. And then they both lost those men and were left having to find the strength to move on for the sake of their children. Despite these similarities, Lorraine was never a source of comfort for Gina. Reflecting on this, Lorraine suggests that perhaps she was so hard on Gina because they were too alike. “You are most critical of the flaws in others that you have yourself” (p.207). Is this an excuse? Do you think Lorraine is a hypocrite? Is it too late to make up for lost time?

13. Discuss the notion of betrayal. How is Lorraine’s secret about Gina and Vicky’s father a betrayal of their trust? Does the truth alter their childhood memories? How does May feel betrayed by her mother’s emotional distance? Do you think the characters are cognizant of their betrayal to those closest to them? Why or why not?

14. How do Gina and May decide to celebrate their memories of Drew? What could Lorraine have learned from them? How do you keep the special memories of a loved one alive?

15. Describe the three women in this mother-daughter generational story. They each have succumbed to emotional and traumatic pain in their lives, impacting how they relate to one another. Were you drawn to one woman more than another? How are they different? Who do you sympathize with the most? What bonds them together? Have they offered any insight into your own relationships with your mother, sister, grandmother, etc.?

Enhance Your Book Club

1. There are so many delicious descriptions of food throughout the novel, from bacon brownies to pierogies to, of course, grilled cheeses. Consider hosting a potluck dinner inspired by the food mentioned in the novel for your next book club meeting. Each member can bring his or her favorite dish!

2. Gina is an obsessive list-maker. She finds them essential to organizing her thoughts. If you don’t already do so, try writing to-do lists either for work or for your personal life. Make sure to cross off each item on the list as you accomplish it. How do you feel once you complete a task? Do you find that to-do lists help your productivity, or are they a distraction?

3. When Gina learns the truth about what her mother had kept hidden, she writes down ten questions in her notebook that she’d like answered—“questions she hoped would help her sort out her muddled emotions” (p.164). This book is divided into ten sections by each of these questions. Now that you’ve read the book, answer these questions as Lorraine, and then as Gina. Next, ask your own parent(s) or grandparent(s) the same questions. What do you learn? Do you feel closer with them?