Women &Their Friends:

1. Jackie asks, "Why do we women feel that we have to answer to one another?" Is this an integral aspect of female relationships? Or is Jackie's reaction an assumption provoked by a habit of defensiveness?

2. What are your thoughts about each of Jackie's three friends — Anne, Nic and Kris?

3. How does Jackie's growing self-confidence alter the balance and nature of her friendships? Does the note of reconciliation with each of her friends ring true to you?

4. Why do Jackie's friends find her expectations about happiness disturbing? And at one point in the novel Nic even suggests that children should be taught not to want so much, do you agree or disagree?

5. Do you like making new friends? Does it come easy to you or do you have a hard time letting down your guard? With your close friends, do you share all your thoughts, or do you edit yourself?

Dating:

6. How do Jackie and Kai complement each other? Are they as dissimilar as Jackie — and her friends — believe?

7. Does age really make a difference? Why do you think most people find it easier to accept the idea of a romance between a younger woman and an older man more acceptable than a romance between a younger man and an older woman?

8. Are you optimistic about Jackie and Kai's chances of successfully carrying out a long-term long-distance relationship? Why/why not?

Facing Reality & "Growing Up":

9. Jackie asks "Does anyone else ever feel like a faker? Does anyone else ever feel like a pretend grown-up, someone masquerading as a mother or the nice woman next door?" What's your response? Why do people seem to think it's important to play the part, wear the clothes, even when they don't feel like they fit into the role?

10. Kai comments "Nothing lasts forever... eventually everything always ends." What do you think he means? Does he change his mind during the course of the novel? How do you see this affecting his relationship with Jackie? Have you ever been in a situation where you had to let go because something beautiful had to end? How did you cope with it and learn to move on?

11. As the story opens, Jackie is riddled with guilt and self-doubt, but her self-analysis eventually fuels questions that help her re-examine her life, routines, friendships. How does her sense of responsibility impact her struggle for greater self-fulfillment?

12. What does Kai's advice, "choose happiness", tell you about him and his experiences? Is Jackie correct in judging that life is easy for him? Why does Jackie find it difficult to follow his advice?

13. The physical challenge of surfing and her attraction to a surf instructor reconnect Jackie with her own body and with sexuality in ways she has not experienced in years. Are her insecurities and skepticism warranted? If so, why does she "feel like me, only better"?

14. Have you reached your big 4-0 birthday yet? If so, how did you celebrate? Did you dread turning 40 (or 50 or any other landmark birthday)? How does age impact a woman's self-image and self-esteem?

Motherhood & Marital Status:

15. What do the two slices of birthday cake that Jackie cuts for herself reveal about her relationship with her children? In your opinion, what defines a healthy parent-child relationship?

16. Nic demands, "How are you ever going to get used to being single if you're always running away?" Is there such a thing as a 'proper' single life? Does being a parent make spending time on your own, independent needs taboo?

17. Jackie wryly considers that what she really needs is a wife. Some of the tasks she attributes to this wife are those of a housekeeper and a secretary — in other words, a servant. Is this a true reflection of what wifehood entails for today's woman? Does it differ from your ideal?

18. The divorce of Jackie and Daniel upset the status quo of their circle of friends, and even those who remained by Jackie's side disapprove of some of her life choices. In what ways could it be argued that the lack of support actually proves beneficial for Jackie?

19. Jackie says "I don't know if it's life, motherhood, or marriage but women start giving pieces of themselves up, little by little, year after year, and then one day you wake up and you're not even there anymore. All the things that made you fun and fiery and hopeful... are gone." Can you identify with her point of view?

20. "Our children become part of the world so fast and it's our job to prepare them, transition them, our job to love them and gracefully step back and let them go." How do you relate to this as a parent? Do you think you'll be prepared to let your children go when the time comes?

Society's Double Standards
21. Are women more prone than men to letting society decide what is acceptable behavior and what isn't? Do men stop to think 'What will people think or say?' before they go after what they want?

22. Wanting more out of life is a key issue for Jackie. But the harder she fights the ordinary, the expected, the conventional, the deeper she runs into conflict with her family and her surroundings. Is she justified in her pursuit, or, as those around her seem to think, unreasonable or even unfair? Do you think that by the end of the book she has been successful?

Location & Its Impact:

23. Jackie's trip to Hawaii is a turning point for her. What roles do the contrasting climates and cultures play in Jackie's learning process? Would a vacation anywhere else have had the same effect?

24. Jackie's Seattle is bleak and cold, a place of figuratively and literally broken things and people. Does her decision to abandon her trips to Hawaii mean that she has finally resigned, settled like her friends? If Kai had not changed his mind about traveling, what direction do you think Jackie's life would take?

25. As an interior designer Jackie brings order, harmony, and practical sense to her clients' homes. She also enjoys entertaining guests in her own home. What does "home" mean to Jackie? How does her definition help or hurt her?