book discussion questions for Second Time Around
Special thanks to reader Kim Murdock for requesting these!

- One of the themes in this book is the contrast between fantasy and reality—the idealized images we create in our heads about other people and careers. Brooke, for example, finds out that the realities of running a bed and breakfast are a far cry from what she’d been imagining. What are some other jobs that our culture glamorizes and what are the hidden drawbacks?
- Brooke, Jamie, Anna and Cait bemoan their choice to be English majors now that they’re in their 30’s, but when they were in college, they followed their hearts and studied what they really wanted to learn about. Do you think they truly would have been better off in the long run if they had studied finance or gone to law school? If you had a child who wanted to devote his or her career to the liberal arts, would you support this decision? Why or why not?
- Cait hides the true nature of her work-in-progress from her friends, her boyfriend, and her academic colleagues because she feels that her writing isn’t sufficiently “serious”. She allows the expectations of other people to shape her feelings about her own accomplishments. To what extent does this apply universally—women get caught up in trying to meet other people’s goals for them instead of creating and embracing their own?
- Jamie describes herself as “the token Jezebel amid a trio of good girls.” What role does Jamie play in the group of friends, and why do you think a self-proclaimed “bad girl” is drawn to “good girls” (and vice versa)?
- Truth time: what is your dream job? Do you think you’ll ever give it a try, and if not, what are the biggest obstacles—physical, financial, or psychological—that deter you?