1) Ann’s journey by steamboat to Pittsburgh provides the opportunity for reflection and change, as travel often will. Why does Ann’s first trip to the city change her?
2) How does Mr. Miller influence Will Hanby? Have you ever known someone like Mr. Miller, who has stepped into a parental role for a young person unrelated by blood?
3) Jacob Good behaves in ways that are shocking, by normal standards of decency. What do you think motivates him in his relationships to others?
4) After Ann reads The Mysteries of Udolpho, she reconsiders her attitude toward sentiment and benevolent acts. Do you think some novels can either benefit or harm the way people think? Why or why not? And if so, can you think of examples?
5) Where is Will spiritually at the beginning of the novel? How and why does he change by the end of the novel?
6) Will’s trials could have left him a broken person, but instead he chooses to help others in similar abusive situations. Do you know anyone who has turned pain into a desire for serving others?
7) How does the environment (weather, countryside, cityscape) reflect what is happening in the story?
8) Why does it take Ann so long to understand her emotions toward Will?
9) Will spends much of the novel repenting his behavior with Emmie Flynn. Why do you think he crossed his own moral boundaries and did something he later regretted?
10) Dueling was controversial in the nineteenth century. Gentlemen felt it was necessary to defend their honor, but many spoke out from the pulpit against the practice. Do you think there could be a legitimate reason for a duel in 1826?
11) In the afterword, the author describes which parts of the novel are factual and which have been fictionalized. What is the difference between a historical account and historical fiction? What are the advantages and disadvantages of fictionalizing history?