Stuck in the Middle with You: A Memoir of Parenting in Three Genders Reader’s Guide Questions
Jennifer Finney Boylan 1. On page 7, author Jennifer Finney Boylan compares her own marriage to Deirdre with that of
Grenadine Phelps, whom she meets at a fencing match. “By almost anyone’s measure,” she writes, “Deedie and I are the
dangerous outliers, and Grenadine and her husband Mr. and Mrs. Normal.” Do you think of Jennifer and Deirdre as
“outliers”? What makes a family “normal”?
2. Boylan writes, “It is my hope that having a father who became a woman has made my two remarkable boys, in turn, into
better men.” Do you believe this is true? How do you think having a parent who is “atypical” affects children? Does it
strengthen a family, or place it at risk?
3. Throughout Stuck in the Middle with You, we observe Boylan worrying that her sons will suffer by not having a
father, that it will be harder for them to learn what they need in order to become men. And yet, her sons appear to
flourish and thrive, and she notes that she has taught them some “masculine” things, like splitting wood, regardless of
her gender. How important is having both a mother and a father for raising well-rounded children? Is it possible that
the sex of the parents is less important than the values they teach or model?
4. Deirdre Boylan says that “marrying Jenny was the luckiest thing that ever happened to me.” Do you think this is
true? If you were married to a spouse who emerged as transgender, would you be able to stay married to him or her? How
important is gender to a relationship? Do you believe that we fall in love with a person, with a body, or both?
5. Boylan writes that “womanhood—like manhood—is a strangely flexible term.” She even notes that there are “genetic”
women who have a Y chromosome. Is there a single thing that you believe defines someone as a man or a woman? Is, as
Boylan suggests, our gender identity more “strangely flexible” than we first suspect?
6. “One of the things about manhood I learned from my father,” Boylan writes, “is that it’s a solitary experience, a
land of silences and understatements, a place where a lot of important things have to be learned alone. Whereas
womanhood, a lot of the time, is a thing you get to share.” Later, she suggests that fathers are more playful than
mothers, and that mothers worry more about their sons and daughters. How do you think mothers and fathers are different
in the way they interact with their children?
7. Richard Russo, in describing his largely absent father, says, “[I] can either take what he’s offering . . . enjoy
it and let the rest go, or . . . be bitter and resentful. For me [it was] just an easy choice. . . . Just to have fun
with him.” Are you surprised about Russo’s remarkably forgiving approach to his father’s many shortcomings? Have you
ever been able, in your own life, to choose to “take what someone’s offering” and “just have fun,” instead of giving in
to the very human instinct to feel resentment or anger?
8. Boylan’s children, at a remarkably young age, seem to adjust to the change in their parent, and go so far as to come
up with a new name for her—“Maddy,” their combination of Mommy and Daddy. Are you surprised by the way the boys so
lovingly accept something that many adults might have struggled with? Do you think the boys might have struggled more if
Boylan’s transition occurred when they were older?
9. Edward Albee asks, in his interview with Boylan, whether parenthood “mean[s] making or is it the being?” He says,
Boylan “never birthed [her two sons]. Isn’t that a different quality of parenthood?” What do you think? Are parents who
are not biologically related to their children different from parents who are? Does the experience of actually going
through labor and giving birth change the relationship between parent and child?
10. Dr. Christine McGinn notes in her interview that the definition of motherhood and fatherhood are changing. She
tells the story of being transgender, (from male to female), saving sperm, and later using that sperm so that she and
her female partner could have children. Both mothers breast-feed, and both mothers are the biological parents of their
children. Do you view this, as Boylan seems to, as primarily a story about love, and adaptability? What does it mean to
be a mother or a father in the twenty-first century, when the definitions are changing so rapidly? Will all this change
have a positive effect on children, making them, possibly, more accepting of the diversity of human experience?
11. Cartoonist Tim Kreider discusses his affection for the biological mother and half sisters he first meets in his
forties. What do you think accounts for the connection that biological siblings can feel? Later, he suggests that while
he’s glad to have found his biological mother, he is unlikely to undergo a similar search for his biological father. Why
would an adopted child be more curious about his or her biological mother than his or her father?
12. Boylan’s mother, Hildegarde, seems to accept Jennifer as her daughter, even after raising her as her son, in spite
of the fact that she is a conservative person, both spiritually and politically. What do you think explains Boylan’s
mothers’ ability to put aside her confusion and simply believe that “love will prevail”? If your child came out to you
as transgender, would you be able to accept him or her with the same love that we see from Hildegarde? Is there anything
that could happen that would make you turn your back on your child? Or should the love between parents and their
children be a love without conditions?