Twain & Stanley Enter Paradise

Reading Group Guide Questions for Discussion

1. Stanley and Clemens came from very different backgrounds and held differing, and often contrasting, beliefs. What do you think bonded them together?

2. Why was Stanley so keen to have Henry Hope Stanley adopt him? What does this longing say about the notion of family? Why do you think Stanley was so secretive about the “truth”?

3. Throughout their lives Samuel Clemens and Henry Morton Stanley experienced some form of a rebirth. Do you think they felt completeness in their lives and careers as a result of this rebirth? What does their trajectory say about namesakes and identity?

4. Samuel, Henry, and Dorothy all wrote diligently, whether it was through private correspondence, through journals, or through fiction. How do you think the writing process changed them and their outlook? Do you find a similar catharsis in writing?

5. Discuss the parallels between the relationships of Dorothy and Stanley and Livy and Clemens. How did these similarities bring them together?

6. Both Samuel and Henry were very open and honest during Dorothy’s portrait sittings. How did her portrait process help or hinder her relationship with each of them? What do their revelations say about them?

7. How did Clemens and Stanley’s perspectives on slavery change throughout their friendship? Did they ever come to terms with their treatment of others? Do you think, as Samuel said, they were both just a product of the times? Why or why not?

8. Though both Stanley and Clemens achieved unbounded success, they often felt like outsiders within their circles. How did this need for belonging and acceptance influence their decision-making and outlook?

9. How do you think fame influenced Samuel Clemens and Henry Morton Stanley? Do you think their relationship prospered from it? Was there perhaps any jealousy? Why or why not?

10. In the end, what were Stanley’s religious beliefs? What does “The Cabinet Manuscript” and the truth behind it reveal about his beliefs? Why was Samuel so interested in other’s beliefs even though he himself wasn’t particularly religious?

11. Why do you think Dorothy was so attracted to spiritualism? What does Stanley and Samuel’s ambivalence toward spiritualism reveal about their relationship with her? How did their beliefs help each of them during times of grief?

12. During his last portrait sitting, Samuel debated what and how much to tell Dorothy about “The Cabinet Manuscript.” Do you think he was open and honest with her? Is it important for her to know the whole truth one way or the other?

13. Dorothy ultimately decided to leave out Henry and Samuel’s journey to Cuba in The Autobiography of Sir Henry Morton Stanley. Why do you believe she did this? Why did she diminish their friendship in his memoir altogether? Do you think she respected their wishes in the end? Why or why not?