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A Letter to Teenage Boys, From Someone Who Used to Be One

Author and performer Jacob Tobia opens up about how growing up as a boy felt like being forced to sacrifice your softness and femininity.
Jacob Tobia as a child (L), photo courtesy the author. Tobia in 2017. Photo by Greg Doherty, via Getty Images.

Jacob Tobia is a writer, performer, producer, LGBTQ advocate, and author of the forthcoming memoir, Sissy.

Puberty arrived a bit ahead of schedule for me. One day I was a cute lil’ pipsqueak; the next, I was a clumsy giant with oversized limbs. Add to that the fact that I’m Arab American (read: hairy as hell) and it would be an understatement to say that my teenage years came on fast.

But it wasn’t so much the bodily changes that struck me—it was the social shift. The fact that for all the physical maturity I was suddenly gaining, I was expected to give up important parts of myself in return.


Young guys often feel that the moment they sprout a whisker, they must grow up on the spot. Our bodies change, and we take that as a signal that we must change our personalities in turn. As a gender nonconforming kid, that’s where the fun stopped for me.

When I was a child, I would fearlessly express my femininity; playing dress-up, coloring princesses, and raiding my neighbor’s bin of Barbies every chance I could get. I never wanted to become an adult, because I knew that along with adulthood came the expectation that I’d finally learn to get my gender “right,” learn to perform masculinity “properly,” and learn to “be a man.”

So, when my body began to change, I didn’t experience excitement. I felt grief. With every inch I grew physically, I grew more fearful of the future. With no blueprints from parents or pop culture to help me figure out what my future was supposed to look like, thinking about life as an adult felt like staring off a cliff.

If you’re a teenage guy—even if you’re a straight, cisgender teenage guy—I imagine that you can understand what I’m talking about. On at least some level, you’re probably having to grow up a little too fast for your liking, and you’re likely uncertain about what that means.

As teenagers, uncertainty begets conformity. When we aren’t sure what’s going on in our lives and we don’t know what’s happening to our bodies, we try to blend in by mimicking the people around us and the characters we see on TV and online.


For boys, more often than not, those images are of action heroes, soldiers, fighters, and men with hulking muscles. They’re of people renowned for physical prowess and athletic ability. They’re of people who represent a narrow mold of archetypal masculinity.

With only a touch of confidence, you can build a world that leaves more space for your personhood, kindness, and sensitivity.

In the process of trying to fit into this mold, we are asked to sacrifice quite a lot. We are asked to give up our gentleness, grace, kindness, sensitivity, flamboyance, and enthusiasm; our ability to explore different clothing, fabric, texture, and color; our ability to be publicly emotional, with the exception of showing anger and aggression. Gay or straight or queer, cis or trans or something in between, every male-assigned teenager in our culture is pressured to give these things up. It feels like a mandate.

But what if I, as someone who’s been there, told you that you don’t have to sacrifice those parts of yourself? What if I, a genderqueer adult who was at one point an insecure teenage guy, told you that you get a chance to determine what adulthood and masculinity look like for you? That you have the ability to be better than and different from generations before?

Here’s the thing: every teenage guy in the entire world is insecure, unsure of how to be in the world, just trying to get it right. And when challenged by someone with only a sliver of confidence, insecure people are often easily swayed. This means that the pressures of conformity, although they feel so insurmountable, can be transformed through sheer defiance. In other words: You can change the model of masculinity simply by insisting on defining it for yourself.


As a teenager, I was something of a church youth group star. When I first joined as a sixth grader, there were some pretty strict unspoken rules about masculinity, one of which was: Girls are allowed to dance enthusiastically when the praise band plays songs, but boys are supposed to be chill and not dance too much.

I hated that rule. I wanted to shake and shimmy and do all of the motions to all of the songs about Jesus and how great he was. I wanted to throw my hands up in the air and bop side to side and get down with my bad self (for the Lord, of course). But I couldn’t, because that wasn’t what guys did.

Then a miracle happened. One Sunday night, a high school senior guy who played guitar player in the praise band joined the girls at the front of the sanctuary and, by the grace of Goddess, went for it. He danced exuberantly, jumping when you were supposed to jump, getting low when you were supposed to get low, throwing his hands in the air like he just didn’t care. Because he didn’t care.

Overnight, the rules changed. All of the sudden, it was cool for guys to dance, to make a show of the whole thing, to be dorky and uncoordinated and expressive and fabulous.

Right then I learned that, as a teenage guy, if you decide that you’re going to wear whatever you want regardless of whether or not it’s “masculine enough,” odds are everyone will go along with it if you’re confident. If you confidently tell your friends that bullying someone else isn’t okay, they’ll likely stop. If you confidently claim your gentleness and sweetness and femininity, people may actually be impressed. And if you confidently acknowledge that being cruel, tough, or physically imposing has nothing to do with adulthood or manhood, your friends just might get with the program.


Do you love yourself enough to embrace the fullness of your gender identity—femininity and all?

With only a touch of confidence, you can build a world that leaves more space for your personhood, kindness, and sensitivity.

Obviously, this isn’t equally easy for everyone. If you’re the only queer kid or the only person of color or the only culturally different kid in your town, transforming social norms can be more complicated. It can take more energy and finesse, and the stakes might be higher. Remember: you never have to challenge social norms at the expense of caring for yourself or keeping yourself safe.

But here’s my challenge to all of you straight, cisgender, socially secure teenage guys out there: Are you confident enough to acknowledge that your heart needs tenderness? Do you love yourself enough to embrace the fullness of your gender identity—femininity and all? Are you brave enough—scratch that, empathetic enough—to challenge the social norms around you?

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It took me a while to get it right. It took me a while to find that courage. But today, I walk through life with the same self-assuredness that that guitar player showed in church so many years ago. I define exactly how masculine and feminine I want to be. I choose how I’m going to show the fullness of my gender identity to the world.

Because here’s the truth: the older you get, the more you’ll begin to realize that growing up doesn’t mean growing out of your femininity—it means growing into it.