1. As it turns out, neither Cait nor Julian has perfectly correct information about the other when they make their decisions. At each step of their relationship, do their actions (or inactions) make sense to you?
2. Is Julian a stalker? A romantic? Is this a love story?
3. What role does music play for the characters in The Song Is You? How and why does music “reopen” Julian’s world? Does it “pay him back”? What does the narrator mean by a “mutual possession”?
4. What do Billie Holiday and the recording of “I Cover the Waterfront” symbolize for Julian’s father? For Julian?
5. Alec’s gallery uses a cocktail napkin that reads: “following the act of love, all creatures grieve.” Rachel resents Julian’s “retreat from feeling,” his fading out to “present less and less of himself to hold on to.” How does Rachel grieve? What realizations do Julian and Rachel reach on their own? Together? How are grief and memory intertwined?
6. “You have to reclaim yourself somehow, or you’ll walk forever like this: among the living but not one of them. Nobody will touch you.” How does this advice relate to Julian’s role as muse to Cait? Why does he consider being her muse “plenty, for now”?
7. Describe the significance of how Julian and Rachel met with regard to what we know about their relationship and Julian’s eventual relationship with Cait.
8. How does technology both promote and hinder connection in the novel?
9. Discuss how aspects of music—art, talent, fame, nostalgia, feeling— can simultaneously inspire both self-love and self-loathing for characters in The Song Is You. How does the struggle for permanence relate? Courage? Longing?
10. On the subject of singers, Julian suspects that “the only real ones, the pure ones, were the dead ones.” More broadly, how does this statement ring true in Julian’s life? Cait’s? Rachel’s? Do you agree?
11. Discuss the significance of space and silence in The Song Is You: between characters, in songs, onstage, and even “the gap between the man and the music.”
12. How and why does Julian reach the conclusion that Cait is the “necessary catalyst” to making Carlton “a present joy in his life” rather than a “semisweet torture from his past or a future stolen from him”?
13. Explain the significance of the Japanese sleeper stories Julian’s father told him as a young boy in relation to the novel. Do you agree with Julian’s father’s conclusion that “love is not sufficient. It never has been”? Does Julian? How do Julian’s and Aidan’s reactions to their father’s stories reflect their differing relationships with him?
14. Why does Aidan delete Cait’s voice mail from Julian’s answering machine? Do you agree that this is “best for everyone”?
15. In Budapest, Julian insists that “a perfect solution, a perfect ending and a perfect beginning” existed. Why is a “factual soft focus” required in Julian’s “perfect” world? Given this, how do you interpret the end of the novel? Is it a “perfect ending”?