On a recent Friday afternoon, I spent a few minutes in our commons area catching up with two senior football captains. Both were wrapping up their college-selection processes and looking forward to graduation; they were also more talkative than normal and especially reflective in thinking about their experiences. We may have talked for 15 minutes, but later that evening, after running our out-of-season workouts and heading home, I realized that short conversations like this one are among my favorite moments of the school year.
At first, it was a little puzzling to me why this brief conversation had such a positive effect on my
day and even my overall outlook; certainly, I have had hundreds, if not thousands, of similar
conversations in 20 years as an educator. Slowly, though, I realized: it was the first such
conversation I had with students during a year that was so different due to COVID-19. For good
reasons, this past year has offered less time for our students to simply be together, and it has
also meant fewer opportunities for us as teachers to spend time together with them. Reflecting
on how much the conversation affected me led me to wonder: What else have we as teachers
and parents of boys learned to value even more highly as a result of the challenges and
limitations of the past year?
We often hear from researchers that adolescent males pull away from close friendships with
other males and experience isolation to avoid appearing “less masculine.” Much of the literature
and even popular culture takes for granted that males resist showing emotion to “man up.”
There is, of course, merit in this research; as educators and parents, we have a responsibility to
think carefully about how we conceive of masculinity and what it means for our sons and
students. Thinking about these statements, though, has led me to consider the times when
boys and young men do not behave according to stereotypical expectations.
Dr. Judy Chu, a lecturer at the Program in Human Biology at Stanford, and Dr. Niobe Way, an
Associate Professor in the Department of Human Psychology at New York University, point out,
though, that boys “influence and are influenced by the environments in which they develop” and
that “understanding how boys respond, experience, perceive, resist, and influence [their]
cultures and contexts is critical to understanding their development.” School life is one of these
contexts in which boys and young men interact. And, in my experience, the young men I teach
and coach develop incredibly close relationships, exhibit emotion, and demonstrate vulnerability.
One of our football game-day traditions is our “Mission Period” – a time set aside roughly three
hours before kick-off for our team to be together and to reflect on our values and objectives.
Sometimes, we invite a speaker, but, more often, our time together becomes an open forum on
a given subject related to our program. Sessions have included discussions ranging from how
fear affects us to the meaning of commitment and the effects of adversity. During these periods,
there have been many remarkable examples of young men sharing their emotions. To be sure,
some of this is limited to the context of our game, such as when football players share with
teammates their fears of getting hurt just hours before a game. Still, there are other times when
the conversation transcends our sport: In one mission period focused on purpose, a young man
who was relatively new to our school team shared with teammates and coaches his recent loss
of his father and how this affected him in preparing to play. Tightly packed together in a room,
after a shared meal, and with little prompting, young men preparing to play a sport that many
associate with the most stereotypical notions of masculinity consistently do not play to type.
While some might dismiss “Mission Period” as a form of compartmentalized sharing, permissible
only within the context of the team or sport, I frequently see similar examples in the classroom.
Just months before the outbreak of the pandemic, I devoted our first classes after winter break
to reading and discussing Peggy Orenstein’s essay, The Miseducation of the American Boy. In
her work, Orenstein contends that adolescent males face narrow paths to masculinity and that
following these paths leads young men to engage in an array of negative behaviors. Sensing
some students might feel defensive and rather certain some students would seize on the limits
of her argument as a way to dismiss her points (her essay does rely on observations of a small
sample of young men), I chose to have students engage in a very specific process of reflection:
I asked them to discuss an experience from their own lives that Orenstein might use to support
her arguments and to explain what her reasoning might be before discussing whether they
The discussions and writing that followed were rich. The students’ reflected on childhood
experiences involving a father encouraging his son to fight back against a bully rather than
involve a teacher, on seeing a friend reluctantly break up with his girlfriend only because of
pressure from his male friends, and on how a Mixed Martial Arts watch party led a group of
friends to cheer each other on in a series of actual fights. In every reflection, these young men
in their junior year of high school offered thoughtful examples. Then, having provided material
that one could reasonably cite as evidence of Orenstein’s views, the young men reflected on
their own feelings about these moments. Students wrote about their desire to “portray emotion”
and expressed hope that adulthood means “growing out” of feeling insecure about expressing
emotion and asking for help. Moreover, these thoughts carried over into our class discussions; I
emphasize this because expressing such vulnerabilities and admissions aloud is dramatically
different from sharing them in written form with an audience of one.
Just like their peers participating in team mission periods, the young men in my English class
defied type, and I know that certain teachers and coaches of other young men could share
similar stories. Such instances raise an important question: Why do the young men described
behave differently in different contexts?
A few months ago, I encountered an especially inspired colleague who teaches drama to our
middle schoolers. As we discussed the challenges of the year, she shared a thought I have
turned over in my mind frequently. Teaching her class of masked and physically-distanced
middle school boys in a cavernous theater rather than her small drama classroom is different,
she noted. More specifically, she commented about the lack of intimacy in this year’s
classroom. Normally, such intimacy arises from day after day of close contact. Having had the
privilege to observe her class in action, I felt like I understood: Acting – performing a variety of
roles and expressing a wide range of emotions – involves incredible risk-taking, especially for
middle school boys. Trusting classmates and believing the classroom is a safe place for such
expression are the foundation of her instruction.
My colleague’s thoughts were especially helpful. Indeed, as I think back on my students who
wrote about and discussed Orenstein’s essay on masculinity, I cannot help but note that their
thoughtful work occurred over halfway through the school year in a classroom of 13 students
who had been in school together for at least three years, many of them for longer.
Ultimately, in considering what I have come to value more greatly as a result of our experiences
during the pandemic, I realize just how much that context matters: In the right contexts, boys
develop the confidence to share who they are, how they feel, what they fear, and who they hope
When boys and young men develop trust in their peers and the adults surrounding them, they
gain the confidence to be authentic in sharing who they are and how they feel. Our challenge
as teachers and parents of boys is to support our students and sons in developing such trust.
We are best able to do this when we create spaces for boys and young men to express their
feelings and offer them structures that make it easier for them to do so.
As I look back on the conversation with two seniors that led to this reflection, I realize that it was
a simple moment and recognize the danger of over-generalizing. Still, my experiences and
those of my colleagues have reminded me that education is a series of simple moments, and it
is our responsibility as teachers and parents to be mindful of each opportunity to create the right
contexts for boys to thrive.