6. Jack is famous for telling stories. Is there a difference between the stories Jack tells to Annie and the ones he tells to the people he’s conning? Are stories necessarily lies?
7. Jack promises to leave Annie a million dollars. Of all the promises he made, and broke, he keeps this one. Why does he keep this particular promise? Is this the one promise Annie would have chosen for him to keep? Which promise that Jack broke do you think Annie would have traded for this one?
8. Like the puzzle at Pilgrim’s rest, there are many different pieces of Annie’s life that have to come together before she feels fulfilled. In the end, it was Dan who put the final pieces together, who helped her make her life complete. What do you believe it takes to make a life complete and fulfilling?
9. Annie said of her father, “He’s a crook. That’s a fact.” to which Raffy replied, “Facts have nothing to do with this.” Is Jack really just a criminal, or is there more to him than Annie wants to admit? What kind of person do you think Jack really is?
10. Look at the family history, as told by Kim, in chapter 6, from “The Boss” to Annie, what traits do all the Peringrine’s have in common? Are there any exceptions? What traits are shared by your family? Are there any exceptions in your family?
11. Sam tells Clark that she wants Annie to be happy, “Fall in love and be happy,” she says. Does falling in love necessarily make people happy? Did it make Annie happy?
12. Annie spends much of the novel wondering about her father and her ‘real’ mother, even though she has Sam and Clark. Who is Annie’s family? How do you define family? Who makes up the family that you have chosen for yourself?
13. What’s your opinion of Brad? Does the manner of his death affect your view of him?
14. Sitting at La Loca, Annie goes through her father’s old business cards and admits that she loved him just as much as everybody else who had fallen for his schemes, and that “love was the biggest con there was.” Did Jack con Annie and the rest of his family? Do you agree that love is a con? When have you felt conned by love?
15. Look at Clark and D.K’s reaction to Annie joining the Navy. Both of them are veterans of the Vietnam War with vastly different experiences and feelings towards the military. How has that affected their views of world? If you know anyone who was or is in the military, how has that service affected their world view?
16. When Jack covered up his father’s murder with the fake suicide note, was he really protecting Sam? Or was it about protecting his mother or himself? What would you have done in the same situation? In what situations would you consider it acceptable to evade or lie to the authorities?
17. Our history can shape who we are as people. Jack and Sam came through a very sad and abusive childhood to grow into very different people. How has your childhood shaped your present? Do you have siblings that grew up with you, but turned out to be very different from yourself? Why do you think that is?
18. Annie had been searching for her mother all her life, while Ruth never knew she had a daughter. What do you think Ruth and Annie were feeling as they sat across from each other at that table in Cuba? How do you imagine you would have felt in Annie’s shoes? In Ruth’s?
19. Annie, Sam, Clark, and Jack all face death or abandonment at some point in their lives. Sam takes comfort in movies, Annie in speed. How has death affected each character’s approach to his or her own life? Have you experienced a traumatic loss that drastically affected your approach to your life? In what ways did you behavior change after that loss?
20. Look at the different ways Sam and Annie respond to the news that Jack might be dying. Compare them to the family of Coach Ronny Buschstabe, whose funereal Annie accidentally attended. Which family do you relate more closely with? Is there a “normal” way to grieve?
21. Annie started this story at 90mph in her Porsche and ended it walking down the aisle and then standing at a grave. What happened to make Annie slow down in life? What events have occurred in your life to encourage you to take things a little slower? Did you always recognize those events or people at the time?
