Reading Group Guide

The introduction, discussion questions, suggestions for further reading, and author biography that follow are intended to enhance your group’s reading of Allison Winn Scotch’s Time of My Life. Allison is the author of the novel The Department of Lost and Found and is also a magazine writer whose work has appeared in Parents, Glamour, Redbook, and Shape. She lives in New York with her husband and two children.


About this book:

Jillian Westfield has the perfect suburban life straight out of the upscale women’s magazines that she obsessively reads. She’s got the modern-print rugs of Metropolitan Home, the elegant meals from Gourmet, the clutter-free closets out of Real Simple, and the elaborate Easter egg hunts seen in Parents. With her successful investment banker husband behind the wheel and her cherubic eighteen-month-old in the backseat, hers could be the family in the magazines’ glossy Range Rover ads. Yet somehow all of the how-to magazine stories in the world can’t seem to fix her faltering marriage, banish the tedium of days spent changing diapers, or stop her from asking, “What if?”

Then one morning Jillian wakes up seven years in the past. Before her daughter was born. Before she married Henry….Armed with twenty-twenty hindsight, she’s free to choose all over again. Sharp, funny, and heartwarming, Time of My Life will appeal to anyone who has ever wanted to redo the past and will leave readers pondering, “Do we get the reality we deserve?”


Questions for discussion:

1. What were some of the similarities between Jillian’s situation and her boss Josie’s? 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 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 not, 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, whom did you want Jillian to end up with: Jack, 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 her life in another direction. 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?


Suggestions for further reading:

The Myth of You and Me
The Next Thing on My List
Kissing Games of the World