Skip to Main Content

New York Times bestselling author Pamela Redmond delivers a beautifully written novel about three generations of women in New York City and the experiences that shape and connect them to each other.

The Possibility of You weaves together three interlocking stories involving three women dealing with issues of pregnancy and motherhood at key moments in history of the last century: On the brink of the First World War and the dawn of the modern age; as the liberalism of the ’60s and ’70s gave way to Reagan’s 1980s; and during the autumn of Barack Obama’s election. Contemporary heroine Cait, an African-American journalist raised by white adoptive parents, goes on a search for her birth mother inspired by her own unplanned pregnancy. Orphan Billie travels from her hippie upbringing in San Francisco to discover the upscale New York grandmother she never knew existed. And Irish nanny Bridget loses the boy she cares for and loves in the 1916 polio epidemic, only to try and replace him with a child of her own.  
 
Delving into the complex emotions that lie at the heart of unplanned pregnancy, motherhood, and the definition of family, this sweeping inter-generational saga illuminates the struggles of these very different women—and shows how the search for belonging is a connection that remains universal.

This reading group guide for The Possibility of You includes a note from the author, discussion questions, ideas for enhancing your book club, and a Q&A with Pamela Redmond. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.


A Note from Pamela Redmond 

I had book clubs in mind when I wrote The Possibility of You. Exploring timeless issues that affect women—women of my generation, of my daughter’s generation, and of my mother’s and grandmother’s generations, too—as well as the way things have changed over the decades made conversations and debates come alive in my head. I longed to hear women talking about those issues, having those conversations, out loud.

If you’re lucky enough to be a member of an intergenerational book club, this novel would be a perfect pick. Alternately, your book club could invite your mothers or daughters (or both), or friends and relatives of different ages, to the meeting at which you discuss this book. The seed of the idea for The Possibility of You involved both my grandmother and my daughter, who never met. After looking up my grandmother’s name on the Ellis Island website and discovering that she’d arrived in 1911, when she was twenty-two years old, I realized she was the same age as my daughter, who had just moved to Paris. Two young women, separated by four generations and nearly a century, both embarking on independent lives in foreign countries and having experiences that, in the end, must have felt very similar.

I suddenly was able to imagine my grandmother as a young woman in a way I never could before. While the reality of her individual life in New York was unknowable—she wouldn’t talk about it, and there was little written about the lives of Irish maids and nannies beyond the most offensive stereotypes—I was able to research the era and create a Bridget who might well have been her.

I, myself, moved to New York in 1976, and while there was no Maude or Bridget in my life, no Jupiter, and no baby, either, I did spend a week at a friend’s grandmother’s apartment on the Upper East Side that felt a lot like the house on Sixty-fourth Street, and I went through a pregnancy scare that left an indelible mark on me.

Of course, young women today have so many more choices, so much more information than my grandmother or mother or I even had when I was in my twenties. And yet, the feelings surrounding those choices, the difficulty of those decisions, has remained much the same.
 

Topics & Questions for Discussion

1.  Why does Cait’s unexpected pregnancy inspire her to search for her birth mother? How does the fact of her own adoption influence her feelings about being pregnant and the possibility of having a child?

2.  Motherhood is a central theme in the story. Of the characters that are mothers, whom did you find to be the most empathetic? How about the least? What does it take to make someone a mother—is it a genetic bond? or an emotional one?—and why?

3.  How does Cait’s life—emotionally, socially, and economically—compare to Billie’s when she was faced with an unplanned pregnancy more than thirty years earlier? Given Billie’s situation, was her decision to leave her daughter and seek a new life for herself understandable? Why or why not?

4.  Describe Bridget’s relationship with Maude, both before and after Floyd’s death. Why do you think Bridget remains with Maude for so many years? How would you define their relationship in one word?

5.  The scene in which Cait finally meets Billie is the only one told from both characters’ perspectives. How does having each of their viewpoints enhance the story? During their conversation, what does Cait come to realize about her past and her future? What is her opinion of Billie?

6.  In what ways does Cait’s search for her birth mother give her a new understanding about Vern and Sally, her adoptive parents? How does her relationship with Sally, in particular, change over the course of the story?

7.  From physical appearances and sexual preferences to upbringings and ambitions, Billie and Jupe appear to embody “nothing but contradictions” (p. 15). What accounts for their close friendship? How does Billie so misjudge their relationship?

8.  How does the issue of race play out in the novel? Discuss the scene on pages 163–173 when Jupe joins Billie, Bridget, and Maude for dinner. Afterward, Jupe disagrees with Billie that Bridget is the more racist of the two older women—and that Maude, in fact, was not being “really nice” throughout the evening as Billie believed (p. 173). Whose perception of the situation is more accurate? How so?

9.  Discuss the historical aspects of the story, including the suffragist movement and the Heterodoxy Club, birth control restrictions, divorce laws, the attitude toward Irish immigrants, and the polio epidemic. What, if anything, did you learn that surprised you?

10.  The Possibility of You spans nearly a hundred years. What were the most dramatic changes from generation to generation in terms of choices and opportunities for women, including those related to marriage and motherhood? What things have remained essentially the same?


Enhance Your Book Club


1.  Given that family is a prominent theme in The Possibility of You, allow members to invite their mothers, daughters, or other special guests to join the discussion.

2.  Have each member research a historical aspect of the book—such as the Comstock Laws, the Heterodoxy Club, the building of the subway tunnel between Manhattan and Brooklyn, the polio epidemic of 1916, or figures like Emma Goldman, Margaret Sanger, and Beatrice Hinkle—and share their findings with the group.

3.  Cait and her friend Sam meet up at a “groovy—Sam’s word—cocktail lounge . . . made out to look like a soigné lounge in old Saigon, or maybe Shanghai” (pp. 151–52). To set a similar scene for your book club gathering, converse by candlelight and serve Gin-Gin Mules. Here is a recipe for concocting the ginger-flavored drink: www.epicurious.com/recipes/drink/views/Gin-Gin-Mule-232358.

4.  To learn more about Pamela Redmond and her writing, visit www.pamelaredmondsatran.com.


A Conversation with Pamela Redmond


There are two epigraphs in the book, one from Philip Roth’s
The Human Stain and the other from Kara Walker’s Letter from a Black Girl. What was it about these two passages that resonated with you?

The Philip Roth quote speaks to how unknowable our family histories, the lives of our mothers and grandmothers, are to us from the present. Cait goes looking for the truth about her parentage, and the reader finds out much more about her history and the foundations of her life than she can ever know. We all have that curiosity about a past that can never be fully revealed to us, and we’re all shaped by experiences that we may never discover.

I saw an exhibition of Kara Walker’s art, which I love, early in the process of writing this book. Besides being inspired by how she rewrites African-American and women’s history, I thought the feeling in the quote of two people wrapped up in a hate-love relationship, the way Maude and Bridget in particular are, especially resonated with this book.


What inspired the idea to have a character who searches for her birth mother? Is adoption a subject in which you were previously interested or one you have personal experience with?


Originally, this book was only about Billie and Bridget, and there was no contemporary story, so when I decided to add a present-day character, I needed to give her a compelling reason to dig into the past and that’s how I came up with the adoption story. Then, the more I read about the struggles of adopted adults searching for their identities, the more interesting the subject of adoption became.

While I am not an adoptive or birth parent and was not adopted myself, I’ve had several close friends and family members who’ve had personal experiences with adoption. I have heard their stories and seen their struggles on every side of this issue for years. Even in a happy adoption, as Cait’s was, there are struggles.


Can you share with us the significance of the title
The Possibility of You and how it relates to the story?

The Possibility of You
connects with all the relationships in the book, from Bridget’s search for the possibilities for her future beyond being a servant, to Billie’s quest for Jupe’s love and for a family, to Cait’s curiosity about her birth mother. The babies of these women exist primarily as possibilities. And, of course, most centrally, to the women in the story as well as to all of us, there is the possibility of who you can become as a person and what you can make of your life.

 
There is a lot of fascinating information in the novel, from statistics (Frank’s clients searching for birth parents are 90 percent female) to historical snapshots (the mania that gripped the city during the polio epidemic of 1916). What sort of research did you do for the novel? How long did it take you to write it?

I worked on this novel for more than five years and did a tremendous amount of research. I knew from my grandmother’s marriage certificate that she’d gotten pregnant before she was married, a secret that provided the kernel of the book’s drama across the generations. Early on, I visited the American Irish Historical Society on Fifth Avenue, whose gorgeous town house provided the model for the house on Sixty-fourth Street.

I also went to the Ellis Island Library and listened to oral histories of Irish servants who came to New York in the years before World War I. At the New York Historical Society, I discovered a 1916 street atlas that showed something called the Hospital for the Ruptured and Crippled, which led me to the polio epidemic. I interviewed a Yale medical history professor, Dr. Naomi Rogers, who’s an expert on the 1916 epidemic, along with an adoption detective, genetic specialists, adopted adults and adoptive parents, and experts on Irish immigration and the early birth control movement.


You’re the author of several baby-naming books, including
Beyond Ava and Aiden: The Enlightened Guide to Naming Your Baby. Do you use these resources when selecting character names? Along with Bridget, do any of the character names in The Possibility of You have special significance or meaning?

My first working title for this book was The Bridget. Bridget was my grandmother’s real name and she changed it to Bertha or Bea; I never knew why until I discovered that “the Bridget” was a derogatory term for an Irish maid. Naming characters is different from naming babies in that you’re not starting with a clean slate; when you choose a name, you have some sense of who you want this person to be. I kept changing Billie’s name from Billie to Lily and back again, but once she firmly became Billie, she got a lot tougher than she’d been as Lily.


Reading about real-life figures like Margaret Sanger and Emma Goldman, with their actions put into historical context, is pretty powerful. Which women’s rights advocate do you find particularly inspiring? What more can you tell us about psychoanalyst Beatrice Hinkle?


Beatrice Hinkle was fascinating and has been largely forgotten. She was one of the first women psychoanalysts in the United States, she translated Jung into English, and she was an extremely prominent and influential woman of her day. But I was able to find out only little about her until I gained access to a secret library in New York-Presbyterian Hospital, where they have her papers: astounding. But while Hinkle is amazing to me, Margaret Sanger is the women’s rights advocate I find most inspiring. She went against the law and conventions to help poor women gain the right to birth control that wealthy women enjoyed via private doctors.


A memorable moment in the novel takes places when Billie is in a nightclub and speaks with a woman who had given up her own baby for adoption. That woman turns out to be Patti Smith. How did you discover this fact, and why did you work it into the story? Are you a fan of Patti Smith’s music?


I am a huge Patti Smith fan—her rendition of Bob Dylan’s “Changing of the Guard” is my absolute favorite song—and I was inspired to add this very late in revisions after reading her wonderful book, Just Kids. She wrote so honestly and movingly about giving up her child for adoption that I could imagine this scene very well taking place. It feels very real and vivid to me.


The Possibility of You
spans three generations. What insights did writing this book give you into how things have changed for women over the last century? Were there any important issues you specifically wanted to address, such as post-partum depression or access to birth control?

Definitely access to birth control is huge, but beyond that, as a woman who came of reproductive age at the time Billie did, I really wanted to write about how relatively naive and idealistic and also repressed people were about sex and pregnancy in the 1970s, supposedly the age of sexual freedom. I even got a copy of Our Bodies, Ourselves, which every young woman had at the time, and in there was a lot about abortion but very little about pregnancy.


An interesting aspect of the story is how some of the women in the Heterodoxy Club, who are advocating for women’s rights, have a derogatory attitude toward Bridget. Why the contradiction? Did you come across anything in your research that sheds light on this?


The women in the Heterodoxy Club—which was real and the common denominator for famous women of that day—were all wealthy and educated and upper class. There was then, and for decades to come, a casual classism and racism among people who on the other hand were fighting for women’s rights or other kinds of social equality. And the Irish, of course, were seen as an inferior race. The parallel between that ethnic prejudice and the prejudice against Italians and blacks was something I wanted to explore.


You say on your website that
The Possibility of You started out as a historical novel focused on an Irish nanny whose young charge dies in the 1916 polio epidemic. How did it transform into a story set in three different time periods, including the present?

It started out as a historical novel with a much pared-down version of the 1976 Billie story as a framing story. But the framing story never really worked; it just wasn’t compelling enough. One early reader said the 1976 story consisted of Billie saying, “And then what did you do, Grandma?” Zzzzzzzzz. And so I kept looking for ways to make the framing story more modern and more compelling and also to make the events of 1916 matter more going forward.


What do you most enjoy about writing historical novels? What can you tell us about the one you’re currently working on?


This is my first historical novel and I’m hooked. There was a steep learning curve: I remember asking writers I admire like Geraldine Brooks and Jodi Picoult how they knew when to stop researching and start writing, and whether they did all their research before they began. Research some, write some, research some more was the message. And at some point you need to let go of all that great history you’ve learned and just let the characters live and breathe.

I’m working on two new novels now, both compelling and wrestling for my attention. One is another historical novel, set again in 1916, in the Adirondacks at a great rustic estate owned by a young widow, modeled on Margaret Vanderbilt, whose husband has gone down with the Lusitania. Grief stricken, she travels north to sell the place, only to encounter the amazing bed that the resident woodsman—hunky, naturally—has spent the winter building for her on her late-husband’s instructions.

As with The Possibility of You, there is also a present-day story that parallels the historical tale. The other book is a contemporary novel, funny but I hope also deep, about four characters— two women, two men—searching for happiness in a modern world that promises a lot but often doesn’t deliver, at least not in the obvious ways.
Photograph by Gregory Vigliotti

Pamela Redmond is the New York Times bestselling author of more than twenty works of fiction and nonfiction, including Younger, How Not to Act Old, and 30 Things Every Woman Should Have & Should Know. She started publishing novels, cofounded the world’s largest baby name website Nameberry, got divorced, moved from New Jersey to Los Angeles, and changed her name, all after the age of fifty. The mother of three and grandmother of one, Redmond’s website is at PamelaRedmond.com.

“Seamlessly weaving the present with the past, THE POSSIBILITY OF YOU is an exploration of love and family, of race and relationships that combines the best elements of a family saga with an intricate, Chinese box of a mystery story. Complex and compelling and compulsively readable."

—Geraldine Brooks, Pulitzer Prize-winning author of PEOPLE OF THE BOOK

“[E]ngrossing…Bring this on your next beach vacation. Order a margarita. Open to page one and dig in.”

Glamour

"Deeply satisfying and enjoyable and juicy. I loved the characters, loved the history, and felt like I was absorbed in a world that I didn't want to let go."

—Peggy Orenstein, New York Times Magazine columnist and author of CINDERELLA ATE MY DAUGHTER

"Every mother, daughter, wife, and friend will love this novel about women's lives across the generations: their passions, their challenges, their unbreakable bonds. A gift to savor for yourself and to share with every woman you know."

—Dorothea Benton Frank, New York Times bestselling author of FOLLY BEACH: A LOWCOUNTRY TALE

“For big fans of stories of mothers and daughters and intergenerational ties, Redmond delivers.”

Library Journal

More books from this author: Pamela Redmond