- What is the significance of the book titled The Art of Fielding in… The Art of Fielding? Does Henry learn anything from it? What does he learn and how does it affect his life?
- Does the book-within-a-book remind you of any other books you've read?
- Why do you think Harbach chose these four POV characters: Henry, Mike, Pella, and Guert? What do our protagonists have in common? What sets them apart? What other perspective(s) do you wish Harbach had included?
- Is The Art of Fielding a book about baseball? How is The Art of Fielding like a baseball game? What else is it about? What is each protagonist's relationship with baseball?
- What causes Henry to choke on the field? How does he cope with this? What could he have done differently?
- Is Henry better at baseball by the end of the book? Is he better at life? How can you tell?
- Why does Pella decide to exhume her father's body and dump him in the lake? Is that what her father would have wanted? What would her father's life been like if he hadn't died? Would he and Owen have stayed together?
- How does the scene at the end of the book compare to the scene at the beginning of the book? How have Henry and Mike changed? In what ways do they remain the same?
- Think of other baseball stories you know, either books (like A Prayer for Owen Meany) or movies (Field of Dreams) and compare them to The Art of Fielding. Besides baseball, what themes do these works have in common?
- Westish College capitalizes on its connection to Herman Melville. What allusions to Melville's work do you notice in The Art of Fielding? Is baseball like Moby Dick in any way?
- The Art of Fielding is almost as famous for being a good book as it is for the $650,000 advance author Chad Harbach was paid. Why do you think he fetched such a high amount for this book? Was that paycheck deserved?
- In 2014, The Art of Fielding was optioned for a cable TV show. Whom would you cast? Why is this book being adapted for TV instead of a movie?