1. Would you separate Valerie’s life into two distinct periods–before Hemingway and after Hemingway? Why or why not? What would be the dominant characteristics of each of these eras?
2. What about Valerie’s personality enabled her easy assimilation into Hemingway’s madcap life? How does she view being with him as an adventure? In what way does she yearn for freedom?
3. Do you feel that Ernest was a Henry Higgins to Valerie’s Eliza Doo-little–that is, did he attempt to shape and mold her? What does she seek to learn from her mentor?
4. Have you had a mentor relationship? How was your relationship similar to or different from Valerie’s relationship with Ernest?
5. Did you know much about Ernest Hemingway before reading this book? Have you read other biographies of Hemingway? Is the picture of him that emerges from Running with the Bulls similar to or different from your preconceptions of Ernest Hemingway?
6. How are Valerie and Ernest both scholars of writers and good writing? How does Hemingway’s advice to Valerie about writing shape her career path? Based on this memoir, what similarities and differences in writing style might Valerie share with Ernest?
7. Why do you think that Hemingway adopted ﬁrst a paternal and then a more romantic interest in his young secretary? Why does he ultimately view her as “indispensable” to his life and work?
8. What do you think Ernest Hemingway’s inner circle might say about Valerie Hemingway and her inﬂuence on his life?
9. “Only with his absence could I appreciate the intensity of his presence,” Valerie writes on page 88. What about Ernest Hemingway is larger than life? How does he become more frail, fragile, and human in the course of this memoir? Ultimately, why do you think he takes his own life?
10. Cuba is a strong presence in this book. How does the prerevolutionary island compare with the place that Mary returns to after Ernest’s death? In your opinion, why did it seem like such a magical place to the Hemingways? Why do you think Cubans still revere Ernest Hemingway, both his books and his memory?
11. Both Ernest Hemingway and his son Gregory grapple with their own internal demons. How does each man struggle in different ways? How do they present their problems to those around them? How would each have beneﬁted from the psychological advances present today?
12. How does Valerie’s interlude with Brendan Behan change her life? What is her attitude about their night together?
13. How does Mary seek to be a maternal ﬁgure? In what ways is she non-maternal? Does her mind-set about motherhood echo Valerie’s attitudes in any way?
14. The importance of leaving a legacy is a theme that courses throughout the book. In your opinion, what is Ernest Hemingway’s most enduring legacy? How does Mary ultimately control her husband’s legacy? What do you hope that the legacy of your own life might be, and who would you most want to shape it?
15. “I came to know a great deal about Ernest, more than I have ever gleaned about another human being,” writes Valerie on page 210. How does this understanding of Ernest Hemingway shine through in this book? How do you think it might have contributed–for better or for worse–to her marriage with Greg? Is there a person who you think might know you better than anyone else in the world?
16. How does loyalty and money ﬁgure into the Hemingways’ inner circle? How does Mary see Greg as a traitor, and vice versa?
17. What about Valerie is so fascinating to the men in her life, from Ernest to Brendan to Greg? How does each seek to guide her? In turn, what attracts her to each of them?
18. What are the clues that Valerie gives early in the book about what was wrong with her marriage? Were you surprised to learn that Greg was bipolar and a transvestite? How do Valerie and Greg’s family help him until the end of his life?
19. Why do you think that Valerie Hemingway chose this moment to write her memoir? How is her viewpoint into Ernest Hemingway’s life a unique one? What questions would you like to ask the author about her life?