1. When do you think the action of the novel occurs? Is there a reason the time was left vague? Is this the "real" New York City?
2. At what point did you begin to suspect that Chase Insteadman was living a fiction? At what point in their story do you think Perkus Tooth understood that Chase had been deceived about his role?
3. Can you accept that Oona Laszlo is responsible for the letters attributed to Janice Trumbull? Is it possible, as a writer, to create another human being more generous, large-hearted, and responsive than yourself?
4. What is the meaning of the wild animals that intrude on the lives of these Manhattanites—the eagles, the tiger? Do they have anything to do with the weather?
5. Have you ever felt that the place where you lived or grew up was being turned into a "simulacrum" of itself?
6. Have you ever tried to care for someone impossible? Are you now? Does Perkus Tooth remind you of anyone in your own life, or did you find Chase's decision to befriend him misguided?
7. At different points in Chronic City Perkus Tooth seems to attempt to sustain himself completely on culture and language, then, alternately, to try to leave culture and language entirely behind and live a "pure" life. Do you think either approach is possible?
8. The author's working title for Chronic City was "Manhattan". The Woody Allen film by that name was often criticized for depicting a Manhattan consisting only of the white upper middle class. Is Chronic City self-aware about the limitations of its characters? Does Chase Insteadman's response to the black kids he meets near the Urban Fjord, or to the black man in the jail cell imply another version of Manhattan creeping into view?
9. What does the gray fog hide?
10. Was Chase unfair to Oona? Should he give her another chance?
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