1. General Impressions 

Gather initial thoughts and broad opinions about the book.

• What genre did this novel feel like to you? Mystery? Noir? Allegory? What other associations did you have with Towles’s style? 
• Does the version of 1930s New York that Towles paints here feel authentic? Does it seem based on research, or is it primarily influenced by other literary depictions? Why or why not?

2. Personal Reflection and Connection 

Encourage readers to connect the book’s themes and characters with their personal experiences.

• Katey believes in the power of choice over that of luck to determine the trajectory of a person’s life; for instance, her choice to cede Tinker to Eve has dramatic and far-reaching results. Have there been seemingly insignificant decisions in your life that turned out, in retrospect, to be momentous? Do you believe that people are primarily the result of their choices or of the lucky breaks they do or don’t get?
• The novel considers different kinds of sexual and romantic mismatches. For example, Tinker and Eve have a loveless but guilt-fueled relationship; Tinker and Anne have a transactional understanding and an affair that the outside world would disapprove of; Katey and Wallace are failed lovers turned friends.