1. The narrator notes that “Will” has several different meanings. Which of those meanings are at work in the title of the book? How do each of the two protagonists relate to their name, and how does their attitude toward it change over the course of the story?

2. The “contemporary” narrative is actually set in 1986 rather than the present. How have sexual mores and the relationship between politics and religion changed since then? Has the United States become more or less like the book’s portrayal of Elizabethan England? How might the story have changed if the contemporary story had been set in 2008 or 2009?

3. The two timelines in the story intersect in four places. Where are they? To what extent do the two stories merge in chapters forty-one and forty-two? How do the intersections affect Willie and William? What does each learn from the experience?

4. Aside from Willie and William, are there any characters in one timeline that have parallels or near-parallels in the other?

5. My Name Is Will has been optioned for a film adaptation. If you were casting a movie of this book, would you have the same actor play both Willie and William? Are there any other roles you’d double-cast?

6. The Fool is a recurring symbol in both Shakespeare’s plays and in this book. What does it mean to be a Fool? Which characters in this book seem Foolish to you, and to what extent are their Foolish choices rewarded or punished?

7. The relationships of Willie and William to their parents is a prominent element in the story. How do the advice, nurturing, and support (or lack thereof) that each protagonist receives from his family affect their development as young men?

8. How do you think Willie’s journey through the different settings of UC Santa Cruz, Berkeley, and the Renaissance Faire reflects Willie’s emotional and intellectual journey?

9. As the subtitle suggests, there is a lot of sex in the story. Do you find it gratuitous, or do you feel it supports the book’s themes of self-discovery and interconnectedness? In what way do the passages about hermaphroditism—from the performance of Salmacis and Hermaphroditus to the digression about banana slugs—advance those themes? What about the Dashka-Willie-Kate threesome?

10. Webster’s defines “hero” as “a man of distinguished courage or ability, admired for his brave deeds and noble qualities.” It defines an “antihero” as “a protagonist who lacks the attributes that make a heroic figure, as nobility of mind and spirit, a life or attitude marked by action or purpose.” Would you call Willie a hero or an antihero? What about William? Which of their actions or attitudes would you cite to defend your assessment?

11. The character of Willie seems to reach a low point in chapter twenty-four, when he wakes up after the threesome and enumerates the mistakes he’s made so far. At that point he resolves to “Do it all. Right now. Today.” How well does he succeed in his plan of action? Are there indications of change in his character from this point forward, or is he just the same old Willie?

12. Some readers have noted that the stakes in William’s story are higher than in Willie’s story. Willie certainly wouldn’t have been hanged, drawn, and quartered if that cop had found his pipe in chapter twenty-six. What do you think this says about the two different times in which the story takes place?

13. There are a number of quirky relationships in the story, from Robin and Willie’s “don’t ask, don’t tell” arrangement to Mary and John’s sharp-tongued ribbing of each other, to the odd couple of Alan and Mizti, to the marriage of convenience that Anne Hathaway offers William at the end. Do you think any of the relationships are successful or have a hope of lasting? Which ones, and why?

14. The novel ends somewhat ambiguously. Where and when do you think the final chapter takes place? Who do you think wrote the “Shakespearean” sonnet at the end? And to whom do you think it’s written? Which, if any, of the women in the novel do you think Willie ends up with? What about William?