1. How would you feel if your ex-boyfriend was getting married before you were? How would you feel if your ex was marrying a fabulously famous Hollywood actress? Would you ever attend an ex-boyfriend’s wedding? Have you ever searched for an ex-boyfriend online or checked an ex’s wedding registry?

2. What is it about Douglas that Brooke loves so much? Why can’t she let him go? Have you ever been with someone you simply could not get over?

3. Brooke thinks that Trip’s family is amazing and Kennedy-esque, even though they’re racist and wouldn’t help Trip find a job after law school --- it was Brooke’s family that did that. Why does Brooke think they are so great, and at what point does she begin to see things --- and the people in her life --- for what they really are?

4. How do Brooke’s and Vanessa’s relationships mirror each other? How do Brooke and Vanessa mirror each other? In relationships with friends, do you tend to be close with people who are most like you or most unlike you? What about in your romantic relationships?

5. Brooke and Jack initially do not get together because they work at the same law firm. Have you ever dated someone at work? Would you ever date someone you work with, even if your company had strict rules against dating co-workers?

6. Nina, a girl Brooke was unkind to in high school, tries to sabotage her. Do you believe in karma and that the bad things you do in life come back to haunt you?

7. Jack dons a kilt for Brooke’s ex-boyfriend’s wedding. What’s the craziest thing someone has done for you out of love? What’s the craziest thing you would do for love?

8. Why do you think Brooke cuts off her hair in the end? What does this symbolize? Have you ever gone through a physical change that revealed how you were feeling on the inside?

9. Do you think that Brooke and Jack ultimately stay together? Why or why not?

10. The novel is told from Brooke’s perspective. How do you think it would be different if it were told from Jack’s?