1. The author writes, “All roads lead back to my hometown.” Why did Amy Dickinson go home again as an adult? What do you think she expected to find? What does “going home” mean to you?

2. Amy writes from the heart, by honestly sharing her childhood joys and disappointments. What qualities resonate with you?

3. The book contains many second chance stories – both the author’s own and those of the other women in her life. Who in your discussion group has a second chance story to share? What can you ascertain from this real life experience?

4. “Marriage was just an assumption I had made about my life and I couldn’t simply undo it,” (page 17). Do you think most women assume that they are destined for marriage and motherhood, and that they don’t have options beyond either role? How does this apply to you?

5. What were some of the good things to come out of Dickinson’s role as single mom? What challenges are unique to these women? How did the author meet, or sidestep, these tests? Dickinson has a complicated reaction to her role as a parent. Do you think she did a good job?

6. “I knew I was destined to live in New York City,” (page 69). Did you decide your future at a young age? What were you determined to do when you got older? Did you amend your plans? Remember, we can’t go backwards, only forward.

7. What did you think of the Mighty Queens in Dickinson’s family? What did they teach her? Who are the Mighty Queens in your life? What have you learned from them?

8. “We are not our best intentions. We are what we do. My husband taught me that,” (page 46). What do you think this statement means? Do you agree with its sentiment?

9. Amy writes her story using a conversational style, as if she is having a cup of tea with the reader. What was your favorite part of the book?

10. Dickinson entitles Chapter 7 “Failing Up.” What does this phrase mean in context of the author? What are examples of the author’s “upward failings?” What can we learn from Amy’s experience?

11. “To me, the two hardest questions to answer have always been, ‘Who am I?’ and ‘What do I want?’” (Page 125). Have you ever asked yourself these questions? How would you answer them today?

12. Discuss this statement from the introduction: “In my family, the women tend to do all the heavy lifting while the men --- well, the men are nice and fine and they love us for a time. Then at some point, it seems they tire of their indeterminate role in our lives, so they wage a campaign of passive resistance, and then they leave.” How is this true for Dickinson and some of her female relatives?  Do you think it’s a self-fulfilling prophesy?