1. Jennie Jerome was one of the first American heiresses of the Gilded Age to cross the Atlantic in search of happiness. Do you think she found it?
2. Part of Jennie’s public persona was her Americanness. In English society, built on notions of birth and class, how was she different? Did she consciously use that difference to define herself? Did it liberate or entrap her?
3. The Dollar Princesses, as they were called, who traded American fortunes for European titles in the late nineteenth century, often married for social status more than love. Did the bargain guarantee unhappiness—or were there compensations?
4. A major influence in Jennie’s life was her father, Leonard Jerome. Was his impact on Jennie positive or negative?
5. Jennie’s parents separated when she was thirteen, and her mother moved the children permanently to Europe. Do you think that was a positive change in Jennie’s life, or an unfortunate one?
6. Randolph Churchill proposed to Jennie after knowing her only three days. Would you marry a person you’d known that briefly?
7. Jennie was a near-concert level pianist, a painter, a writer, and her husband’s chief political strategist, but her talents were limited by the roles accorded to women in the nineteenth century. Was she born too soon?
8. Some of us carry friends from childhood all the way through adult life, as Jennie did with Alva Vanderbilt; Minnie Stevens Paget; and Consuelo Yznaga Montagu, Duchess of Manchester. Do you have friends you’ve known since you were young? How have they, and you, changed through the years? What has affected your relationships most over time? If you had lived in her time, would you have wanted Jennie as a friend?
9. Was Randolph Churchill a victim of his marriage, or a villain? What feelings does he inspire?
10. Jennie was unfaithful to Randolph, and he to her, but they were fundamentally loyal to each other through twenty years of marriage. What is more important in a relationship: fidelity, or loyalty? Is it possible to be faithful to oneself, and yet loyal to others?
11. Charles Kinsky violated many of the rules of his royal upbringing and social position in his lengthy relationship with Jennie. Was his commitment to her difficult or easy? Is Charles an admirable figure, or a failed one?
12. A common criticism of Jennie Churchill is that she was a bad or neglectful mother. After reading THAT CHURCHILL WOMAN, what do you think? What did it mean to be a parent in the Gilded Age, particularly in England, among the upper classes?
13. Who do you think had the greatest impact on Winston Churchill: his mother or his father?
14. How do you think Winston’s childhood affected his later life?
15. Winston nearly died at the age of twelve from pneumonia. Jennie lost her sister, Camille, to a virulent fever. Randolph Churchill went insane from a disease that is curable today. How would living with 19th-century medical standards alter your life?
16. Did Jennie Churchill have opportunities she squandered, or possibilities she wasted? If you were Jennie, would you have lived your life differently?
17. Have you ever been in a relationship affected by a hidden double life? How did that influence your behavior and commitment?
18. Is it possible to appreciate or fairly judge those who lived by the social rules of the past?