1. The Chelsea Hotel is one of the main characters in and of it­self. What does it represent? What is its personality, and how does it change and evolve? How does it affect the lives of the other characters?

2. How do Hazel and Maxine use writing to make sense of the world around them? Where do you think their motivation to write comes from? Do you use writing in a similar way?

3. Do you think the political pressures of McCarthyism are still rel­evant today? Why or why not?

4. What did you think of Charlie and his desire to join the FBI? How do you think his relationship with his father shaped his am­bitions? Were you rooting for him and Hazel? Why or why not?
 
5. When Maxine flubs her lines on opening night, her career doesn’t suffer, but Hazel’s does. Why do you think that is? How would you have reacted in Hazel’s situation? Do you think she has a right to be bitter about the suc­cess of Wartime Sonata’s revival, or should she be grateful?

6. If Maxine had not made the tragic choice she did, do you think she and Hazel would have renewed their friendship? If you were in Hazel’s shoes, would you forgive Maxine? Why or why not?

7. How do Hazel and Maxine subvert or conform to 1950s expectations and gender roles?

8. Do you think McCarthyism made romantic and friendly relationships dif­ficult? Why or why not? If so, what were the complications and the conse­quences of having a relationship?

9. “Maxine’s bravery in the square, as well as now, with the major, astonished Hazel. She wished she were that brash. But she wouldn’t dare question an authority figure. Always the understudy, in life as well as in art.” How does Hazel transform throughout the novel, and does the word “understudy,” which she considers to have negative connotations, change in meaning as well?

10. What do you think influenced Maxine’s best and worst decisions in the book? Would you have made different ones? If so, in what instances and why?

11. The theater district was such a vibrant scene in the 1950s. Did you have a favorite setting in the book? If you could go back in time to any of the places mentioned, which would you choose?

12. How is theater represented not only on Broadway in the book, but also in the political arena today? Does the House Un-American Activities Com­mittee reflect any views held today?