1. So many New York City landmarks lend atmosphere to this novel: the St. Regis Hotel, the Metropolitan Museum of Art, Central Park, the Cathedral of St. John the Divine, and, of course, Tiffany’s. If the novel were set in your town, what local landmarks would it feature? Do you think this novel would be as interesting if it were set somewhere else?

2. Michael says that the role of an imaginary friend is to make children feel less alone and to help them find their place in the world. Do you think imaginary friends help children deal with their lives or keep them from dealing with life head- on? In what other ways do we use our imagination to cope with life or hide from it?

3. When Michael leaves Jane on her ninth birthday, Jane is devastated and says, “I’ll never forget you Michael, no matter what.” Do you think there is one perfect love for each of us? How influenced are we by portrayals of love and love affairs in the media, movies, and on television?

4. Jane is involved in an unfulfilling relationship with Hugh McGrath. Is it surprising that without a good role model for loving relationships from her own parents, she would find herself staying in a bad relationship? With so many of us coming from divorced homes, how can we break the cycle and have successful love relationships?

5. Jane’s play, Thank Heaven, is based on her childhood friendship with Michael. Would you have an interest in seeing the play? Do you prefer the play’s ending where Michael leaves on Jane’s ninth birthday or do you prefer the book’s ending where Jane and Michael meet again as adults?

6. Jane’s special emergency feel- good food is Oreos. Do you have a favorite comfort food? Is it good to avoid your favorite foods or does that just lead to more bingeing behavior? How can you help children so they develop healthy relationships with food?

7. Jane “gifts herself” with a diamond ring from Tiffany’s to wear on her right hand. The salesperson assures her that more and more women are buying them. If you could afford a $65,000 diamond for yourself, would you like one? If a woman does not have a man in her life, do you think it is an empowering act for her to buy her own diamond ring?

8. Michael explains to Jane that when children turn nine years old, their imaginary friends must leave them. But he recalls that when Jane was just four, she told him, “Love means you can never be apart.” Does this statement from Jane explain why they don’t forget each other? How do you explain it?

9. Michael gives up his immortality to be with Jane. Do you think he could have made another choice? Do you support his decision? If you had been presented with a similar situation, what would you have done to be with the one you loved?

10. Michael takes Jane to Nantucket because he doesn’t want to waste a minute of the time they have together. Michael says, “Is it so difficult to imagine or believe that a man and a woman can find happiness together for a little while, which, after all, is all that we have?”Is this the moral of the story for you? If not, what is?