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?