Book Club Discussion Questions for Spinster by Kate Bolick

1. Spinster opens with the following statement: "Whom to marry, and when will it happen—these two questions define every woman's existence." Do you find this to be true in your own life? If so, how have you navigated these expectations?
   


2. On the pressure to marry, Bolick believes, "Men have their own problems; this isn't one of them." Do you agree? Why or why not?
   


3. Edith Wharton coined the term awakeners, "to describe the books and thinkers who'd guided her intellectual studies." One of Bolick's goals is to inspire women and men to find their own awakeners. In your own life, who would your awakeners be?
   


4. Bolick writes, "The single woman has always been stigmatized as a lonely old spinster with too many cats." What makes a woman single? Is it a matter of marital status? Of habits or state of mind?
   


5. The term spinster has a divisive history. What does the word mean to you? Has this changed since reading the book? When you imagine a spinster, what does she look like, and would you ever describe yourself as one?
   


6. How does spinsterhood compare to bachelordom? Does society celebrate the single man?


7. In her relationship with W, Kate senses the "friction between the intimacy we shared and the autonomy required to become the people we wanted to be." Do you think individuals can grow to reach their full potential while in a relationship? Is romantic solitude necessary for personal growth?
   


8. After her mother's death, Bolick takes inspiration from her mother's late-in-life desire to forge an independent path for herself. How do you think our parents' aspirations and choices define the decisions we make? Does this change as we age?
   


9. Bolick's relationship with R creates a crossroad in her life. Have you ever had to make a similar choice? If you were in this position, what would you do?
   


10. Bolick writes, "It never ceases to astonish me how readily we presume to know ourselves, when in fact we know so little." What can we do to better know ourselves? How do you stay in touch with your inner self?
    


11. What is your relationship status (single, coupled, living together, married, etc.)? How does Bolick's experience square with your own?
    


12. Bolick describes the "spinster wish" as "the extravagant pleasures of simply being alone." Are there solitary activities that you love? Are they necessary to your happiness?
    


13. Consider Bolick's five awakeners: essayist Maeve Brennan, columnist Neith Boyce, social visionary Charlotte Perkins Gilman, poet Edna St. Vincent Millay, and novelist Edith Wharton. Which of these women inspired you most and why?
    


14. Of all of Bolick's awakeners, Maeve Brennan's story ends perhaps the most tragically. Yet, Maeve's ability to express herself endures in spite of her circumstances. What did you learn from her? Do you consider her story a warning or rather an example of a unique and full life?
    


15. Each of Bolick's awakeners marry at some point in their lives, yet Bolick maintains that they are spinsters. Ultimately, what do you think makes someone a spinster?
    

The questions above are taken from the full reading guide produced by Crown Publishers. which has a lot of fun, added value material that is worth checking out.

Unless otherwise stated, this discussion guide is reprinted with the permission of Broadway Books. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.