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Hi Polly,

I’m writing because I’ve been pretty confused lately and I love your column and your advice, so I figured I’d share my confusion with you. Perhaps you’ll tell me to seek help from a therapist, but I’m not quite ready to do that yet.

Lately, I’ve been wondering if perhaps I was meant to be born a girl. I’m now a white male in my mid-30s, and I really couldn’t be happier with my life, professionally, romantically (I’m married to a super-awesome girl and we have a baby together; I also have a child from a previous marriage, to further complicate things), socially, financially, etc.

But all my life I’ve been filled with self-loathing. I’ve always been uncomfortable in my skin and with my emotions and I hated myself for it. I’ve always felt like there was some secret part of myself that I didn’t know and if I could just access it all would be well, like some existential version of Gnosticism.

As far as stereotypes go for this type of thing, yes, I played with my sister’s Barbies growing up, though my favorite was a Michael Jackson doll (I also had a Cabbage Patch doll I loved to dress up). But I also loved my G.I. Joes and Legos and other “boy toys.” Even as an adult these stereotypes resonate with me as meaningful. I gravitate toward other stereotypical women things, like yoga and cleanses and “chick-lit”-style memoirs and some rom-coms. But I also like stereotypical guy things like action movies and comics. My speech lately has been peppered with adjectives like “cute,” “lovely,” and “adorable.” These words slip out and I want to reach out and pull them back lest anyone think for a moment I’m gay or a woman or something.

As a kid, I often pretended my name was a female name in my head. I practiced saying it even. I was late to puberty, I have very little body hair, and I was always thin and slight and small. All my life girls have told me I’m one of the few men they like, that there’s something about my energy that’s different from most men. I just thought it was because I was sensitive and shy and compassionate and I listened well. The people I was closest to growing up were girls. I had male friends, but I always felt distant from them.

In high school, I saw the singer of a band wearing a T-shirt that said “Nobody knows I’m a lesbian,” and I thought it was the coolest thing ever. I thought it was so punk rock. Through the years, I found myself wishing I could really be a lesbian. I always brushed this aside though because I thought, WTF, I’m a straight dude, of course I’m a lesbian, I like girls. Only lately have I really started to question why I might be drawn to that designation.

I’ve often struggled to understand men or relate to men, but I chalked that up to me being sensitive and artistic and shy. I cried a lot as a kid, all the way through ninth grade. My emotions, even the happy ones, felt so overwhelming that I became embarrassed to smile or get happy about things because I always seemed happier and more smiley than my male friends. I tried to emulate their detached coolness.

I started cross-dressing, mostly undergarment things, when I was going through puberty, but stopped doing this shortly after due to shame. I was happily married for a stretch, too, which put a damper on these things. I never did this again until recently. I tried it again but I was dissatisfied with my current wife’s clothes because she didn’t have anything I wanted to wear. Nothing was cute or feminine enough.

I’ve often wondered what it’s like to be a woman and have often fantasized about having boobs and what it’d feel like for someone to be inside me. I thought maybe this was just the empathetic side of me. I was never really attracted to boys or men growing up, except gay porn and pictures of penises turned me on. I never wanted to be with a guy and I still haven’t met a guy I ever felt like pursuing, let alone kissing. I also liked porn involving transexuals. All of this has been very confusing for me.

My first wife wanted to move on from our marriage after finding my interest in transexual and gay porn on the computer. She thought I was gay and had thought so since we had first dated in high school. I told her I was just curious, which was true. But gay was never a word I identified with, though I questioned that because of all these other things I just told you about. My vocabulary for these things, having grown up in a rural area, wasn’t that diverse. In the years since I’ve told myself that I’m just attracted to those body parts and to the social stigma of it all.

I’ve often told women I’m jealous of their summer dresses, that I wish men had something similar to wear because they look comfortable and light and breezy. But I’ve often admired women’s clothing that aren’t summer dresses, from scarves to leggings, wishing I could look that way in those clothes. Once, while tripping on ‘shrooms, I joked with a friend that I was secretly a woman, and when he said that wouldn’t surprise him, I felt a little bit of relief that someone saw that in me, but also terrified. Could others know? Do others know? My dad once asked me if I liked boys, but I thought maybe that was a thing all dads ask their sons at some point early on, like a test.

Do I really want to be a woman? I don’t know. I don’t think so. It’s not even a thought that crosses my mind most days. but then some days I see a really cute girl and I die a little on the inside. I used to think I wanted to be with every one of those girls. But sometimes I wonder if I don’t want to be with her so much as be her. That realization, even if not fully formed in my mind, comes with a certain level of pain. Like recently, just this week, I saw a picture recently of an MTF and I hated how cute she looked and how passable, too, like that will never be me, I’ll never be a woman.

As I write all this out, the evidence seems overwhelming, but maybe that’s just what I want you to read. I haven’t told you much about all the other masculine parts of me, but that feels a little irrelevant.

So, where do I go from here? If you share this or reply to it, I’d love to know what your readers think.

Not Sure

Dear Not Sure,

Your words make it so clear how strange and restrictive our ideas of gender are. We live in a world of beautiful colors, but we’re determined to call them all either “black” or “white” and ignore everything in-between — to say all the blues are “black” and the reds are “white” and the yellows are just invisible. Yellow doesn’t even exist. Greens that look more blue than yellow are black. Purples that look more red than blue are white. Orange is something no one should be, because white is less than black, and yellow is invisible.

So first of all, I want to encourage you to immerse yourself in forums where these kinds of gender and sexuality issues are discussed, so you can get a sense of the wide range of ways people define themselves. Sometimes people’s ideas and desires and urges seem to contradict what we believe about one category or another. Most of us need to try harder to embrace the colors that we don’t even recognize, but that are right in front of our faces, in ourselves and in other people.

Even though I’m not an expert in any of that stuff, I’m going to assume that you came to me because you want to hear from me, a woman who grew up marinating in heteronormative black and white. You want me to fumble my way through this with you, and I’m happy to do that. I know I’ll mess up a few things along the way. That’s just what I do. I’m not an expert or a guru. I’m a fumbler. I bumble my way in and do my best.

That’s what I want you to do, too, Not Sure. I want you to create a space where you can do the things you want to do and feel the things you want to feel and say the things you want to say. I want you to experiment and I want you to feel proud of experimenting. Cut other people’s judgments out of the picture. Give yourself some room to be violet and mint green and melon and turquoise. It may be that what you really are, in your heart, and what you really want to be for the rest of your life is [insert category here] or [insert second possibility here]. I won’t dare to assume one thing or another.

It’s also possible that each of these identities might feel restrictive or limiting to you. For me to even speculate on the different ways you might want to live feels a little too pushy and unfair. I still feel like I’d be working with a limited palette, trying to paint you into a corner. There will be people in the comments section doing this, telling you that it’s obvious you’re A or B. That might be really helpful, and a relief, but I would caution you to discard anything that feels too narrow. Only you know what’s right for you.

I would also caution you against feeling like you must take action and DO something at this exact moment. I mean, maybe that’s what you want. Maybe you want to proclaim yourself to the world. I think that if I were you, I would definitely find a really good therapist, and I would talk this out with that person first. Eventually you’ll probably want to have a conversation with your wife, too, but because you have a new baby, this might be a tough time for her to be open-minded about where you are, so I wouldn’t rush that one. I would definitely talk to a therapist first.

Because I can’t possibly know what you want and what your wife will eventually say and how you two will handle whatever comes next, I just want to be someone who says the RIGHT things to you. This is what I would say to one of my daughters if they came to me with complicated or potentially controversial notions about how they want to identify gender-wise and what they want to do to feel more comfortable and authentic in the world: You are just a person. You can be whatever the fuck you want to be. YOU get to decide.

Not Sure, mostly I don’t want you to feel like you have to rush to some conclusion or get corralled into one thing or another. You are who you are. Your complexity makes you interesting. It’s obvious from your letter that you have always owned up to who you are in many different ways, from your childhood forward. Your resilience and ability to keep being who you are — a colorful, rich, nuanced human being against a backdrop of black and white — is inspiring. You don’t have to decide on a neat label for yourself, necessarily, unless that’s what you truly crave.

And by the same token, just because you don’t totally identify with a certain group of people, that doesn’t mean that you might not fit loosely into that group in some sense. A close friend of mine came out years ago, and she often said to me, “But I don’t see myself as a lesbian!” The truth is, most people don’t see themselves as THE SAME as a whole swath of the population. If you were to say to me “You’re a straight, middle-aged, suburban mother,” I would feel horribly misunderstood. “No I’m not!” I’d say. “Obviously I’m some kind of gay teenage boy mixed with a working breed of dog crossed with a dominatrix.” I’m sure I’m violating a bunch of rules and codes in throwing those identities together. But you know what? I’m just flailing my way toward my particular truth. I am an exotic plant, the kind that needs too much rain some weeks and too much sun other weeks and only flourishes in a soil of eggshells, horseradish sauce, and ground-up pomegranate seeds.

We are ALL entitled to our own personally crafted definitions. If we’re being true to ourselves, that authenticity is sure to make us a freak in someone else’s eyes. We all have a right to make our own labels.

I can’t do much for you, Not Sure. All I really want to do here is hand you your own label-maker. Try on some different labels and try loving yourself with those labels. And then throw the label-maker out the window, and see if that feels even better. (And then maybe run and get it again! Who knows?)

There are challenges ahead. I want you to know that no matter what, you are not alone. There is a big world out there, filled with beautiful people who aren’t afraid of that bewildering spectrum of human experience and emotion and identity that transcends black and white. We want you to be your mint-green-melon-turquoise self. Don’t forget that we’re out here. We just want you to feel happy. We just want you to feel whole.

When you feel whole, you create space for other people to feel whole. When you feel authentic, you make room for the authenticity of others. When you tell the truth, you make truth possible in the world. But even if you stay exactly where you are and don’t do a thing, be proud of yourself for making it here. You’re fumbling, maybe, but you’re doing your best. That’s all anyone can ask of you.

Polly

Order the new Ask Polly book, How To Be A Person in the World, here. Got a question for Polly? Email askpolly@nymag.com. Her advice column will appear here every Wednesday.

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