Scot on the Rocks
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 Googled an ex-boyfriend? 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 had someone you simply could not get over?
3. Brooke thinks that Trip’s family is amazing and Kennedy-esque, despite the fact that they wouldn’t help Trip find a job after law school — it was Brooke’s family that did that — and are racist. 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 and Vanessa’s relationships mirror each other? How do Brooke and Vanessa, themselves, mirror each other? In relationships with friends, do you tend to be close with people who are most like you, or most unlike you? 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 at work? Even if your company had strict rules against dating coworkers?
6. Brooke encounters Nina, a girl she was unkind to in high school, and Nina 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
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 manifested 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 through Brooke’s perspective. How do you think it would be different if it was told through Jack’s?
