1) Compare and contrast Olive and Kerrigan’s personalities. What traits cause tension in their friendship? What qualities allow them to support and encourage each other?
2) Why is Sherry initially so reluctant to share with Olive her previous repeat years and the mistakes she made?
3) How does the repeat year influence and inform Olive’s job as an intensive care nurse? Is she right to use her foreknowledge to try to help change patient outcomes, or is she violating ethical standards?
4) Consider the very different ways in which Olive handles her mother’s remarriage. What allows her to change her approach? What new insight does she gain about her mom? About Harry?
5) Is Kerrigan being a good friend when she tells Phil about the repeat year? Or does she betray Olive’s trust? How might she have done things differently?
6) Considering the state of their relationship in the first part of the year, is Olive wrong for turning down Phil’s proposal? Would things have gone differently if she hadn’t? What if she had confessed the truth to Phil early on in the novel? How do you think he would have reacted? Would they have still ended up together?
7) Olive grapples with the question of if her previous year and bad decisions really happened if no one else remembers it. Do you agree with her interpretation or do you think her infidelity and other mistakes are more comparable to a dream?
8) Our past experiences shape who we are in the present. How do Phil’s past experiences help to explain why he was reluctant to forgive Olive? How do they help to explain why he ultimately is able to reunite with her?
9) What are the ways Olive matures and grows over the course of her repeat year? What major lessons does Sherry learn? Do you think this will be their last repeat year?
10) Why do you think Olive and Sherry were given repeat years? Who else in the book do you think could use a repeat year?
11) Are you satisfied with Olive’s ending, or would you have rather seen a different ending for her? What will happen next for her? What will happen next for Sherry?
12) If you could relive a year of your life, what would you do differently? Do you think the events in your life have been shaped more by chance, fate, or freewill?
Reader’s Guide for Imaginary Things
1) At the start of the novel, Anna feels defeated to be returning to Salsburg, which she connects with boredom, failure, and provincial attitudes. What changes her perception of life in the small town, and how does it change?
2) Duffy and Winston each have their own personalities and styles of being a grandparent. How does Duffy demonstrate her affection, and in what ways does Winston show his? How do their different approaches help Anna in different ways? Do you see examples of either in the way Anna parents David?
3) After the end of her relationship with Patrick, Anna speculates that “mania was true love. And it could consume you like it had consumed Patrick, or it could leave you feeling tired and used up, like it had left [her.] Nothing seemed to exist in between.” How and why does her attitude about love change over the course of the novel?
4) Why does it take so long for Anna to see Jamie as someone other than her childhood friend and the “boy next door?” What qualities does he possess that make him a good fit for Anna?
5) Why do you think David creates his dinosaurs? What do King Rex and Weeple individually represent and what roles do they serve for him? In contrast, why does he create the panther and what function does it perform?
6) What do you think really happened between David, Gunner, and King Rex during the disastrous play date? In the world of the novel, do you think that imaginary friends could be capable of physically affecting their environments? What other clues might suggest this?
7) As a child, why does Anna dream up Leah Nola as her imaginary friend? What role does Leah Nola play in her life, and what light does this shed on Anna’s own personality and past?
8) What do you think of Kimberly’s character and the choices she made as a parent? Do you agree with Anna’s assessment of her? Why or why not? Do you think the mother and daughter could ever restore their relationship?
9) Do you think seeing imaginary friends is a hereditary trait, or do you think there is some other reason both Anna and her mom, Kimberly, were given the opportunity to see their child’s imagination? Compare and contrast the ways the two women handle the surreal situations.
10) Did you or your child ever have an imaginary friend? How do you think this and other games of make-believe affect children’s development? In what ways do adults use their imagination? Is there anything we can consider as imaginary friends for adults?