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1. Is Cassie a good mother? A good wife? A good sister? Does she seem to prioritize any of these roles over the others? Which is the most important to her? What should be the most important relationship? Is it possible to ace all of them, or do some have to suffer so that others can thrive?

2. How do you think Cassie’s obsession with Facebook affects the way she sees herself, her family, and her own life? Do you think people are honest about themselves on social media? Can you tell when they aren’t? How does seeing an endless stream of curated information about other people’s lives influence how we see our own?

3. What do you make of Cassie and Leo’s constant text messaging? Cassie seems to think they would be more intimate without it. What’s a healthy amount of electronic communication in a relationship?

4. Cassie lets her relationship with Sid slip away, despite needing her. Is social media to blame? Why do we allow ourselves to drift away from the people we love while keeping up with acquaintances on social media? Is there someone close to you who has the opposite social media tendencies as you do? How does it impact your relationship?

5. Cassie mentions Sid’s beauty several times even though she admits she is being superficial. Do you think Cassie is superficial? What about Sid? How does being beautiful affect someone’s personality? Do you think Cassie is jealous of Sid? Why or why not?

6. Cassie seems to idealize Sid in other ways, too. Is this her being a little sister, or do you think Sid deserves Cassie’s adoration? We only get Sid’s views on Cassie through her letters. How do you think she would describe Cassie if she narrated the book?

7. What if Cassie and Sid had kept in touch the usual ways, via email, phone, and texting? Would they have been more or less guarded? In what ways might their relationship have been different?

8. Cassie finds herself wishing for a “simpler time” upon hearing her grandfather read the letters he exchanged with her grandmother. Does Cassie get her wish? Do you think old-fashioned letters were simpler or more complex than modern communication? How so?

9. What about Cassie and Jenna? What is it about their relationship that prevents them from being friends? Do you trust Cassie’s assessment of Jenna, or do you think she’s been unfair to her? Do you recognize relationships you’ve had with other women in them? If so, were you a Cassie or a Jenna?

10. Cassie doesn’t do much with Jake physically, but is she any less guilty than if she’d had a full-blown affair? Why or why not? Are there degrees of infidelity?

11. Cassie has a turning point just before the blog goes viral. Do you think she would have ended up in the same place emotionally if the blog hadn’t gone public? Or did she need to survive that ordeal in order to fully save her marriage and herself?

12. Where would Cassie, Sid, Leo, Kenny, Adrian, and River be now if the blog had never gone viral?

13. What advice would you have given Cassie if she came to you for help when she discovered that the blog had gone public? Who did she need to tell, and what did she need to tell them? Do you think flying to Singapore was necessary? Or would her efforts have been better spent on Leo? Who was most damaged by Cassie’s actions?

14. Were you surprised by Leo’s reaction? Do you agree with his decision to not read the letters? What would you have done? If he had read the letters, would he still have forgiven Cassie? Do you think she deserves his forgiveness?

15. What about Sid’s reaction? If you were in her position, how might you handle it? Given her problems with Adrian, what do you make of her ability to be supportive of Cassie’s attempt to put her marriage back together?

16. Do you think Cassie and Leo will be happy now? Do you forsee any trouble with their living situation at the end of the book? Where do you see Cassie, Sid, Leo, River and Kenny in five years? Could you move in with a sibling and his or her family?

17. Which sister do you most identify with? Who would you rather have as your sister?