1. Stacy Schiff writes, “It is not difficult to understand why Caesar became history, Cleopatra a legend” (page 5). What are the differences between the two? How are these differences related to gender?

2. Discuss the role of subjectivity in historical records. How does Schiff factor that subjectivity into her account? Do you think it’s possible to document events that are close to us in time? Or do chroniclers’ subjectivities necessarily bias their accounts?

3. How do you think Cleopatra felt as she traveled to meet Caesar for the first time? What are the differences between that meeting and her first encounter with Mark Antony? How did the circumstances of the initial encounters set the tone for the relationships?

4. Despite her political ambition, Cleopatra has been painted as a seductress and siren rather than as a powerful and adept ruler. Do you think it’s still the case that men are said to strategize where women manipulate?

5. Discuss women’s roles and rights in ancient Egyptian and Roman society. Did they surprise you? Why or why not? Women in Egypt enjoyed an equality close to what they enjoy today; it was then lost for some two thousand years. Could that happen again?

6. Although Cleopatra came from a long line of strong female rulers, do you think she felt out of place on a political stage dominated by men? Is there any indication that she doubted her abilities? Can you imagine her in a Roman military camp, for example?

7. Cleopatra lived in an era of rampant murder, covert political alliances, and fierce betrayal. Has human nature changed in two thousand years? In what ways is it different and in what ways is it the same?

8. Do you think that Cleopatra loved Caesar and Mark Antony, or were their relationships purely for political leverage? What makes you think so?

9. What do you think of Cleopatra as a woman, mother, lover, partner, and ruler? Was she admirable or detestable? Why or why not?

10. Can you retell Cleopatra’s story as one of her subjects might have written it? How does it diverge from the Roman account?

11. Why has Cleopatra’s story captivated artists and audiences for over two thousand years? Why does she interest you?

12. Are there any modern women who you would compare to Cleopatra? Who? What characteristics do they share with her? Discuss how these women are depicted in histories or in the media today.