1. How do you feel about Evie’s dismissal from Baker & Smith? Do you think it was justified? How much time do you spend on personal matters during the workday? What do you consider excessive?

2. Evie’s previous boyfriend, Jack, says he doesn’t believe in marriage, yet she pursues a relationship with him and continues to pine after him long after they break up. Why do we always want what we can’t have?

3. Have you ever been tempted to quit the Internet, or at least quit social media? Evie says she knows that what she sees online is not reality, yet it still upsets her. Do you have similar negative reactions to social media?

4. Evie yearns for Bette’s approval in her life. Do you think she shares Bette’s traditional worldview more than she’d like to admit? Does this shape the choices she makes?

5. Before going on dates with men, Evie uses Google to her advantage. Do you think she should have regrets about her former dating habits, or is it a safe rule of thumb to know your date? Do you believe Evie and Edward would have gotten together if she had, in fact, Googled him?

6. What are the top three dating tips that you would share with Evie from your own personal experience? 

7. Evie struggles with being the only single one in her group of close friends. Do you think she handles it well? Do you think it’s possible for friends to be close when their situations in life are so different?

8. There is a recurring theme of jealousy and self-absorption throughout the novel. Are there any times that you may have let jealousy, especially fueled by social stalking, get the better of you? Discuss the ways Evie may or may not have evolved by the end of the book.

9. Fran is the ultimate mother --- supportive, loving and not judgmental. Yet Evie seems closer to Bette. Why do you think that is?

10. In marrying Edward, Evie will become a stepmother to Olivia. Do you think she is ready for that role?

11. What do you think about the Steve Jobs quote at the beginning of the novel? Is technology really “nothing”?

12. Do you think Evie was particularly addicted to technology, or is that the way most people are “wired” these days?

13. Aunt Susan tells Evie that life is better with complication, and Evie dismisses the comment. Do you agree more with Susan or with Evie?

14. Do you believe Evie could have had a happily ever after with either Jack or Edward? Or is there only one right person for her?