Last week, I took my 14-year-old son to the barbershop. As an adult, my visits with Troy at Derby Supply are for me a simple pleasure to which I think most men can relate.  But for a 14-year-old boy, in the twilight zone of adolescence, it can be a strange and maybe even intimidating experience.  For his dad, well, let’s just say that I can still picture him in the chair as a cherub-faced 16-month-old getting his first haircut with a billowy blue apron and Barney on the television monitor in front of him to keep him sitting still long enough for the skilled (and patient) haircutter to do her job.  It’s still a wonder to me how she didn’t cut off an ear or her own finger in that endeavor.

Back then, I took the digital video camera (remember those?) to capture the moment for us and for his grandparents, of course. I remember how we talked about his curls and how we made sure to take some of the hair and place it in a small envelope for a keepsake.  And while he was “brave” and didn’t cry in the chair, he was clearly unsure about the whole thing.  In the end, this particular moment in his life might not have mattered that much, except that we documented it and made it part of our family history by doing so. We even scheduled the cut for when his grandparents were in town so they could share in the “experience.”

Fast forward almost 13 years, too many haircuts to count and one cross-country move, I found myself thinking about that first haircut as I watched him sit down in the old-school chair at Derby.  On this visit, which wasn’t his first to a “real” barbershop, my son got in the chair and looked in the mirror, wiping the hair from in front of his eyes as he said, “What should I tell him to do?”  I looked at him and said, “What do you want him to do?  It’s not my hair.”  (Side note: I’d love to have as much hair as he does on his head — but that’s another story.)

In this moment, I can see in his eyes a glimmer of uncertainty about telling someone what he wants, and what’s more, telling an adult.  I prompt him with a few easy questions.  “As short as mine?” (No.) “Tapered like mine?” (Yes.) “Longer on top?” (Yes, duh.)  Ok then, you know exactly what you want.  Tell him (politely, of course).

Like any great barber, Troy knows exactly how to get his clients to tell them what they want, and this time was no different.  I listened as Troy greeted my son, and got him comfortable in the chair, and readied him for a proper haircut.  I listened in to see how Troy prompted him with some familiar questions, for which my son was prepared.  This experience is one of the many, many small things that boys need to feel confident in these environments that feel “grown-up,” and in which they will find themselves more and more as they navigate their high school years and beyond. In the end, we can prepare our children for these situations by first speaking on their behalf and modeling how we interact with others, next allowing them to “practice” their responses with us, and ultimately, encouraging them to speak for themselves.

This progression is natural and necessary, and can happen at almost any time.  Think about how prepared your kids will be for the eventual moment when a peer offers them alcohol, or to participate in some other potentially harmful activity — will they know how to respond?  The barbershop is, of course, a much safer environment, but it’s a perfect opportunity to allow our children to speak for themselves and interact with people in a way that might seem challenging at first. As I suspected he would, Troy engaged my son in a much more detailed conversation than I did, and helped him describe his haircut exactly the way he wanted. Troy is a master.

There is something special about this experience, too, in that it’s also a chance for us to enjoy an afternoon together in a uniquely “male” way, that I can only imagine women enjoy similarly with their daughters in their salons.  I really enjoy physical activities with my son, like being outside hiking, or playing tennis, but this particular barbershop experience is a bit of old-school cool that transcends generations, and doesn’t place an emphasis on physical capabilities. It gives us a chance to connect in a way that allows us to appreciate the care with which the barbers tend to their clients, and the communal experience of being among other men of various ages and styles.  There’s even a teachable moment in talking about the stack of men’s magazines in the lounge area of the shop.

It was great afternoon for my son and me — but also one in which I could actually feel the years of being his dad catching up with me in front of my eyes.  The days of my speaking on behalf of my son are rapidly dwindling, but I know that moments like these are still some of the best opportunities to help him learn how to stand (and sit) up for himself and become the man he is destined to be.