1. Several of the characters in The Observer have a relationship to art. How does art serve to move the plot forward? How does it connect characters to one another, or divide them? How does it reveal their feelings?
2. Eliza Anderson holds views that today we would characterize as elitist and anti-democratic. Did you find any of those views understandable in the context of early 19th-century Baltimore? Or did you find that her opinions made her an unsympathetic character? If you found her unsympathetic, did that interfere with your engagement in the novel?
3. When Eliza takes on the job of editor of a magazine, she believes people won’t really care about the fact that she’s a woman. A year later, when she decides to suspend publication of the magazine, she feels she’s been persecuted because she’s female. Was she in a sense radicalized by her experience? Do you think she was right to believe that animosity was directed at her because of her gender? Were there other factors at work as well?
4. Do you see any parallels between the rough-and-tumble literary world of 19th-century Baltimore and the Internet of today? Consider the facts that writers for most 19th-century publications were unpaid non-professionals, and that many wrote at least semi-anonymously.
5. Margaret McKenzie is an entirely fictional character, but many of the details of her life are based on historical fact about the lives of working people in Baltimore in the early 19th century. From the information in the novel, how likely was it that someone in Margaret’s situation could earn a living wage? Why or why not? How did Margaret’s view of her family’s economic circumstances differ from the view held by wealthier characters, such as James Cork?
6. James Cork and Margaret McKenzie each end up feeling used in some way by the other. Do you think their initial feelings for one another were sincere? What do you think attracted each of them to the other? Could their relationship have worked, given their personalities and the context of the times?
7. Do Margaret and Eliza, despite their many differences, share some common traits, yearnings, and experiences? To what extent do they recognize what they have in common? How do the things they share drive the story forward or change their perceptions of one another?
8. Dr. Crawford is ridiculed for his theory that disease is caused by tiny, invisible insects—-an idea that anticipated germ theory by over 50 years. Do you think there are theories today that aren’t taken seriously but that will, in time, prove to be valid? Can you think of any examples?
9. What does the novel tell you about how Americans thought of their country in 1807, and how they viewed its relationship to Europe? How do these views motivate or affect the various characters in the novel?
10. There’s no evidence that the real Eliza Anderson continued to write after her very prolific year in 1807. Do you think she did, but that for some reason those writings haven’t survived? Or do you think she devoted herself to her husband and his career? Why or why not?