"Whom to marry, and when will it happen--these two questions define every woman's existence, regardless of where she was raised or what religion she does or doesn't practice... even if the answers are nobody and never." Kate Bolick explores her own answer to the classic questions, arduously and over the years of her own life; she examines their place in society, and the way other women she admires have answered them, mining the lives of female writers who have affected her. The resulting book, Spinster: Making a Life of One's Own, is less a polemic than one might expect, and more a thoughtful, generous consideration of our world, and a woman's best options to honor herself.

Bolick begins with her family background, her loving parents and brother, and her home in Newburyport, Mass. In a personal and family tradition of talking, reading, discussing and writing, Bolick naturally gravitates toward literary models for the life she hopes to build. After her mother's death, she seeks to re-create the conversations they used to share, "not with other, real, live women... but real, dead women, whom I could sidle up to shyly and get to know slowly, through the works they left behind and those written about them." In the opening pages, she introduces her five "awakeners," women of the written word who have offered her lessons about how to live as a woman, married or not. These awakeners are an essayist, a columnist, a poet, a novelist and a social visionary (although each, of course, crosses over and between those categories).

Maeve Brennan (1917-1993), essayist at the New Yorker, offers a loving picture of single city life and an admirable sense of style. She will also come to provide a frightening negative version of the stereotypical single woman's final days. Neith Boyce (1872-1951), columnist at Vogue and representative of the Bachelor Girl, supplies a glimpse into the life of working women, a novel possibility in her time; although as Bolick points out, the chance of sex or sexiness in the workplace presents a "negotiation [that] continues today." Edna St. Vincent Millay (1892-1950), poet and legendary lover, brings revelations. "Her legacy wasn't recklessness, but a fierce individualism that even now evades our grasp."

Edith Wharton (1862-1937), novelist and grand dame ("society's favorite version of the single woman"), built herself a house, the Mount, with two rooms of her own, a public "boudoir" for entertaining and a spare bedroom in which to do her writing. She represents a model for the prioritization of one's work, and also for the work Bolick reluctantly takes on in editing a luxury decorating magazine: rather than mere frivolity, this focus offers another opportunity to get to know herself. Charlotte Perkins Gilman (1860-1935), social visionary and prolific writer (of The Yellow Wallpaper, for example), inspires self-improvement and a different way to go about making a home.

Bolick tells her own story chronologically. As she discovers each of her five awakeners (a term borrowed from Wharton) and the lessons she finds with them, she changes jobs, moves from Newburyport to Boston to New York City, and dates and cohabitates with different men (referred to only by the first letter of their first names). She started using the word "spinster" in her journals in her early 20s, and always considered it a positive appellation, one posing possibility. Her evolving interest in spinsterhood is tracked by all of these layered journeys, the lives and writings of the awakeners interspersed with her own. Along the way, she also makes brief calls on Virginia Woolf, Mary McCarthy, Anne Sexton, Annie Dillard and others. Bolick acknowledges that the subjects of her investigations are all like her: straight white women of New England; diversity is not her focus.

Spinster's tone is charming, by turns confessional, collegial and academic. Bolick's erudition is leavened by a playful, casual tone, even as she references Shakespeare and the Lernaean hydra in a single page. Not only a memoir, Spinster employs research into the lives of the five profiled writers, as well as into history and sexual politics. As the narrator of this voyage, Bolick is amiable, credible and fun to know.

Interestingly, all five of the awakeners eventually married, in some cases more than once. While it thoughtfully contemplates the possibilities for and arguments in favor of women remaining unmarried, Spinster is not a mandate. Bolick does not insist upon spinsterhood for her readers. Rather, she offers assistance in "holding on to that in you which is independent and self-sufficient," whether single, happily or unhappily coupled. The word "spinster," and all it entails--and Bolick makes great strides toward the proud and pleased application of this embattled historical term--is thus a tool for our individual contentedness.

Entertaining, wise and compassionate, Spinster is the result of Bolick's lifetime of meditations, ruminations, angst and joy; of research, reading and appreciation of five intriguing lives; of dating, moving in with someone and time spent alone. While allowing that the coupled lifestyle is fine for some, Bolick's message for readers is a celebration of the delights, challenges, and opportunities of remaining single. --Julia Jenkins

photo: Willy Somma

Kate Bolick is a contributing editor to the Atlantic, and a freelance writer for Elle, the New York Times and the Wall Street Journal, among other publications. She's also host of "Touchstones at The Mount," an annual literary interview series at Edith Wharton's country estate in Lenox, Mass. Previously, she was executive editor of Domino, and a columnist for the Boston Globe Ideas section. She lives in Brooklyn, N.Y. Her memoir is Spinster: Making a Life of One's Own.

Clearly this book was a lifetime in the making. But how long did you purposefully work on it? Did the idea of it change during that time?

Spinster began as a bolt of excitement in 2000, when I first came across 19th-century journalist and novelist Neith Boyce's 1898 Vogue column, "The Bachelor Girl," about her decision to never marry. Until then, I was completely unaware that the public conversation around singledom had such a long history, and after that I couldn't stop thinking about the single woman as a cultural archetype, and collecting examples.

After a few years, I sat down and tried to write a book about how Neith and two of her more-or-less contemporaries had influenced my thinking about marriage vs. not-marriage. It was a total and complete failure. I had no idea how to turn my fascination with their unconventional lives into a compelling narrative, and I was too young to have any insight into or personal perspective on the topic, or even know how to ask the right questions. I put the project aside, but never stopped thinking about it.

Then, in 2011, the Atlantic asked me to write a cover story about the changing face of contemporary marriage, and as I did my reporting and research I could almost physically feel the ghosts of those women from the past perched on my shoulder, taking in everything I learned. After the article came out, I thought maybe I was old enough now to give that failed book another go. In early 2012 I signed a deal with Crown.

From the start, I knew that I'd use my own coming-of-age as an adult as the narrative arc, and feature the lives of my "awakeners" as "love stories"--women I'd found, fallen for, then moved on from. In this way I'd be able to lead the reader through a series of historical and intellectual ideas that might feel dry on their own. Actually plotting that out, though, was maddeningly difficult, and more than a few times I thought I had to abandon that approach and try another.

What started as a fascination with certain lives deepened with research into a more comprehensive understanding of the single woman's place in the social order, and how it's changed across time. The specific economic, political and cultural conditions of each era determine who the single woman can be, and how she'll be perceived.

How was this writing process different from the different kinds of writing you'd done before?

The process of writing this book was so different from anything I've ever done that for months and months I was near-paralyzed with doubt about whether I could do it. Length alone was a challenge--I had to unlearn journalistic tics like concision and speed, and give myself over to the space a book calls for and demands. The primary challenge was learning how to create a narrative; what compels a reader to keep wanting to turn the page? Weaving my own story in with the lives of others in a way that didn't feel thunderingly obvious and clunky was likewise vexing. I also struggled with tone. I've written plenty of literary criticism, personal essays, interviews and biographical articles--how could I find a voice that would be capacious enough to let all these disparate forms coexist under the same roof?

What do you most want people to know about you that's not in Spinster?

The book is officially a memoir, but I had to leave out acres of thoughts and experiences in order to keep the emphasis on what matters: the lives of the women I write about; the history of single women in general. Which is to say, the book is only one slice of me. Dear reader, I contain multitudes!

Could there be a sixth awakener for you, who you just haven't found yet?

Absolutely. In fact, by the time I started writing the book I'd accumulated quite a few awakeners, which I decided to cut down to a more manageable six--the ones who'd influenced me most directly. After I finished the first draft, I realized six was one too many, and cut another. I expect that for the rest of my life I'll keep finding new awakeners. At least, I hope I do.

Are you prepared to be an awakener yourself?

Hah! Well, given that finding an awakener is such a private, intimate process, and one that the awakener her/himself has no idea is taking place, I suppose I could handle it. In this way, I'm much better suited to being an awakener than to being a heroine, who needs to be dashing and daring. I'm not very dashing or daring.

What are you working on next?

Wait, you mean there's life beyond Spinster?! Heh. I love the material too much to even want to think about anything else just yet. After two years holed away writing, I'm excited to finally be back in the world, talking about what I learned. --Julia Jenkins