By Mike Greenberg
William MorrowSeptember 2013

Trade Paperback288 pages, $14.99, ISBN: 9780062220769
Subject: Women's Lives / Relationships / Family

  1. Would Samantha have become friends with Katherine and Brooke under different circumstances? What do the three women have in common besides the event that brings them together?
  2. Samantha is horrified when she finds those pictures on Robert's laptop, but is she partially to blame for invading his privacy?
  3. Why do you think Katherine chose to stay at the company for as long as she did? With her education and experience, she could have found a comparable position elsewhere. Is there a part of her that wants to suffer by witnessing Philip's success? Is there a small part of her that believes she can win him back if she sticks around? Or is it something else entirely?
  4. Brooke stakes much of her own happiness on her husband's satisfaction and his perception of her. Is this problematic?
  5. Brooke says you need three core girlfriends: one who's like a sister, one who knows everything, and one a generation ahead of you. Do you agree? Who occupies these roles in your own life?
  6. Robert seemed genuinely contrite when he went to see Samantha. Would you have taken him back? Why or why not?
  7. Samantha is always trying to help people, and she wants to extend her generosity of spirit to Brooke. Do you think she was wrong in forcing Brooke to share her story? Was she at all motivated by guilt?
  8. Why do you think Brook decides to do what she does? Do you agree with her choice? Do her loved ones deserve to be included in her decisions?
  9. Brooke sees her life as divided into stages – her sweet sixteen, her wedding. What are the stages of your life?
  10. Samantha reflects on her evening with Andrew Marks as "the night [she] learned that [she likes] being pretty." Despite confronting a serious life hurdle, she does not abandon her vanity. Is this something many women can relate to? What does being pretty mean to you?
  11. When Katherine meets Stephen, she knows she has "met the man who [is] going to change [her] life." Do you believe in love at first sight? Are her strong, serendipitous feelings for Stephen in any way related to this phase of her life?
  12. Katherine and Samantha have a few "absolute deal-breakers": a grown-up who calls his mother every day, a man who buys maxi pads for his dog. What are your absolute deal-breakers?
  13. In her last person-to-person to Samantha, Brooke writes, "Please leave me alone." She tells her she'll be in touch when she's ready. What do you think ultimately moved her to reach out? What changed?
  14. Brooke is the only one with a husband by her side, and yet she does not share her secret with him. Is she motivated by fear? Do you think that has more to do with her or with Scott?
  15. In the last chapter, Katherine has run off to Aspen to be with her dream guy, Samantha is dating a pediatrician, and Brooke is laminating meaningful quotes for her fridge. Where do you see them each in five years?