1. What are some of the similarities between Jillian’s situation and that of her boss Josie? What could Jillian learn from watching Josie?

2. Jillian discovers a lot about herself by watching Megan and Josie cope with their various problems. How did these friendships offer her clarity on her situation? What do you learn from your own friends when encountering life’s problems?

3. Motherhood proves more challenging for Jillian than she anticipated, and she laments that no one talks about how hard it can be. Are women these days opening up to all of the realities of motherhood, not just the wonderful parts of it? If so, why do you think that is?

4. If Jillian’s mother hadn’t left the family, would Jillian’s life and perception of herself have been different? If so, in what ways? If not, why not?

5. Both Jillian and her mom seem fated to make the same mistakes over and over. Are we fated to make the same mistakes repeatedly in life, and if so, how do you break the cycle?

6. All of the women in this story struggle to find balance between their various roles in life. Do any of them manage this better than the others? How so? Can that perfect balance be achieved?

7. Was anyone at fault in the breakdown of Henry and Jillian’s marriage? What about in the breakdown of Jack and Jillian’s relationship?

8. Do you think Henry and Jillian end up happy in the long run? What about Megan and Tyler? Josie and Art? What do you think happens to Jack?

9. As you were reading the book, did you want Jillian to end up with Jack or Henry? Or neither?

10. When Jillian goes back in time, she realizes that her memory of events may not be as clear as she thought. What does Jillian gain by looking clearly at the reality of events? Do you think you’ve ever skewed the past, for better or worse, to help you deal with the present?

11. Jillian has the chance to go back in time and see what would have happened if she had taken another direction in her life. How would your life be different if you had taken a different route? Do you ever wonder “What if?” and think about what might have been?

12. Regardless of which fork in the road you take, do you ultimately end up in the same place even if it takes longer to get there?