ask polly

‘I’m Trans and I Feel Unlovable’

Photo: Puneet Vikram Singh/Getty Images

Dear Polly,

I’m a trans woman who came out just over three years ago, in my mid-40s. I lost my marriage and almost all of my friends, but I’ve made a new life in the city. I have a much better relationship with my children now that I’m not seeing them through a fog of depression. The friendships I have now are so much deeper, more joyful, and more rewarding than the ones I had in my old life, and despite all the awfulness that comes with being visibly trans — and there’s a lot of awfulness right now — my life now is so much better than it was before.

Or at least, it is as long as I keep moving. I feel like a shark: if I stop swimming, I’ll sink. So I’m constantly filling my time with concerts and films and creative projects and freelance work and volunteer work because if I have any downtime, all I feel is lonely and miserable. I feel that by coming out I’ve pretty much guaranteed that I’ll be alone for the rest of my life, and that terrifies me.

I didn’t date from my early teens until I met my wife in my very late 20s. I was convinced that my terrible secret, which at the time I thought was just that I liked to cross-dress, would mean instant rejection. I decided to be up-front when I met my future wife, and I told her that I cross-dressed very early in our relationship. She was fine with it, and when I finally worked it all out and realized I was trans, she tried to be fine with that, too. It didn’t work out. What initially began as a lack of attraction to me quickly turned into disgust.

My father rejected me when I came out, too. He wrote me deliberately vicious emails that were thousands of words long. There was nothing feminine about me. Who was I trying to kid? What was I doing to my children’s lives? Had I lost my fucking mind? Those were the nicer things he said, and I’ve heard his cruelest words in my head on a loop pretty much ever since. Whenever I consider even trying a dating app, it’s his voice I hear.

And it’s not just him. It’s our entire culture. I’ve spent most of my life being told that people like me are monsters, and seeing trans women portrayed as deceitful and dangerous and disgusting. For four decades I’ve been told again and again that people like me are broken, dangerous, hideous, unlovable. Just last week at a comedy show I had to sit through a routine where the comic shared his disgust at a dream in which a woman turned out to be trans. That was the entire joke: Trans! Ugh! I’ve heard that one a lot.

I feel like decades of that have poisoned me, and made it impossible to believe that anybody could desire me.

I know trans people are beautiful, and I try to remember the nice things my friends who are women tell me: that I’m pretty, that I’m charismatic, that I’m funny, that I’m kind. But all I see is what I’m not. I’m terrified by the prospect of dating because under the wig and the makeup and the too-small breasts there’s a body I hate, a body that isn’t feminine enough, a body stuck in limbo between man and woman.

In the rest of my life I’ve made peace with and even drawn strength from being trans: I stand up and perform on stages under bright lights, confident and comfortable in my own skin, sometimes looking pretty fierce. I’ve lost the stage fright that plagued the old me.

But when I imagine dating, I lose all that confidence. I can’t bring myself to swipe right because I expect rejection. Maybe it’ll happen when she discovers that I haven’t had surgery, or when she sees my height and build, or when she hears my too-deep voice, or when she finds out my hair is a wig, or…

I know that maybe someone out there won’t mind any of that. But I also know that the chances of finding her are slim, and the chances of being rejected by other women are high. I’m tough, but I don’t know if I’ll ever feel tough enough to deal with that, because the rejections I’ve had in the last few years have been the cruelest kind and I don’t think I can take many, or any, more.

So I keep swimming, because if I don’t, I’ll sink. But each day I feel like I’m getting lower.

Help me, Polly. How do I rise?

Trans and Tired
Dear T&T,

I feel honored that you came to me for help. I’ve been going through some heavy stuff lately that might cause me to question my ability to help you. I’m sure that more than one person is reading right now and thinking, “Oh sweet Jesus, yes, let’s watch this middle-aged, white cis-hetero woman try to grapple with something that is waaaaay beyond her grasp.”

But if I decided that I was too pathetic or too limited to help you, that would be like you going on a date and focusing on what you don’t have: The “right” build, the “right” voice, the “right” hair, the completed surgery, or some version of feminine beauty and power that maybe you’ve imagined your whole life. You might believe that only a trans woman with all of these good things would have a fighting chance, a way of being seen clearly, a reason to be desired and cared for and loved. So in your mind, there’s nothing but rejection ahead.

Let’s start in this hopeless place: There are so many things that you feel like you don’t have and so many things that I feel like I don’t know about you, or that I could never understand without living those experiences myself. But I got your letter yesterday afternoon when I was feeling so crumpled and avoidant and old, motherfucker, so old and weird and delusional. I’ve been on this high for months, and it’s like my plane got shot out of the sky by a stray missile. And even though my plane didn’t explode into a million pieces, even though I should feel grateful just to have survived, I felt so tired yesterday. I knew I should be celebrating, but yesterday I felt exhausted and small. And I was disappointed in myself for feeling that way.

Feelings are pretty resistant to concrete instruction in the wake of a stressful change in atmospheric conditions. Feelings are going to do exactly what they want to do, and you can either get onboard or feel even worse about everything. Your shark self — that imperative to keep moving at all times — is you trying to stubbornly direct feelings that don’t want to be directed. You can keep busy, thereby ignoring your feelings, but when you slow down, you’re overwhelmed by all of the dark feelings you’ve put off facing.

I don’t want you to surrender your entire being to some inky black abyss any more than I want to do that. But letting in a controlled portion of these sensations and emotions will help you, and ground you, and make you feel more whole. You have to feel your sadness in order to feel your joy. Scrape the shame out of your sadness, if you can. With identity dilemmas and giant identity-adjacent changes, shame is such a huge part of the picture, and your dad’s thousands of words don’t exactly help.

Whenever you feel shame, this is what I want you to remember: Angry, unhappy people who hold forth on what they think you’re doing wrong are like tiny insects screaming about the evils of the sun. They have strong emotions paired with zero concrete knowledge, so their opinions couldn’t be less relevant. What’s less compelling than a father who doesn’t want a child to become anything but a sad echo of what he is? What’s less interesting than a comedian who wants to stick his dick into a sad echo of what he beat off to as a boy? Let’s just let the ants keep carrying their little bits of bullshit across the same ground in the same pattern until they’re fucking dead and move the fuck on, okay? These ants do not interest us. They hold no answers. They are barely even trying. They are not looking up at all. The sun offends them. The sun is unfair and unethical. The most brilliant thing on the planet leaves them cold.

Do you know what you really are, inside? That’s what I want to ask you. Because I feel like I know what you are, even from here. I know that you’re full of stubborn, brilliant light. I don’t know exactly how I know this. Maybe I felt it when you told me that your relationship with your kids is better than it’s ever been. That made me love you and your kids in equal measure, and it let me know that you already know what you’re doing. It’s not just that you’re no longer depressed. You have good instincts. I have the same thing going on with my kids. I’ve always been honest with them about who I am, because I want to model that self-acceptance for them, even when they can see that I’m an obnoxious show-off, among many other unlikable things. A few months ago, I wrote some wild dystopian fiction and emailed it to my kids on a whim (even though, yes, we still live together! They’re 13 and 10!). They both responded quickly and said they liked it a lot and I should write more stuff like that. Kids are the opposite of ants. They love to be surprised. They invent new routes and wander through the world in new ways every day. They love the fucking sun and they’re not afraid of it.

I also love that you’re performing. I think you knew that performance was a route toward self-acceptance for you — and much more. You’re confident onstage. You tap into your body’s swagger and flair when a lot of people are watching. You understand your own power in that space. I’m like that with writing.

Over the course of the past few years, I’ve carried the swagger I feel on the page into my actual life. I can feel my power in the company of other people. I’ve always been socially assertive, but this feels different. This is about connecting with the essence of who I am while being open to the essence of who other people are. It’s not a mundane feeling. It’s like being in the zone during a performance. Your body knows things that you don’t know consciously. You follow your body. You trust your instincts.

You have the same power that I have, is what I’m trying to say. You have the power to connect with almost anyone you meet, if you set your mind to it. And when someone resists that energy, that’s not really about you or something you’re missing. It’s not a rejection. It’s about them. Because when you say to another person, “I like something about you, I can feel it, and all I want from you is some connection, all I want is to meet on some neutral ground and see what’s here,” that’s a very respectful, neutral, generous offer. I feel like that state of openness is reflected in your relationship with your kids and your relationship to the stage. You already know how to do it. Now you need to invite it into your new friendships and new romantic connections.

I can’t tell you if dating apps are the way to go. I think for right now, you have to meet people in real life and tap into your connections face-to-face. You have to practice and learn to trust those new connections before you move into a riskier space with strangers. You have to be patient.

Move away from monitoring other people’s reactions, and move into a place of monitoring your compassion for yourself. The seismographs of other people’s eyes hold no meaning for the earthquake. You are a force of nature that transcends their sometimes narrow concerns and fearful projections. Move into a place where you’re the one occupying a gentle, neutral open ground, and they can choose to join you there or not. Move into a place where you watch to see if this person is an ant or a child who loves sunshine.

Because you are a child who loves sunshine, and you are very, very easy to love. That’s just obvious, and I don’t even know you at all. All of the noises inside your head about what your build means and what your lack of surgery means and what your dad’s words mean don’t serve a purpose, but they’re lovable because they’re vulnerable and complicated and real. They’re interesting blasts of bewilderment, like the flashing lights at a disco right before a truly wise soul enters and gathers all of the eyeballs in the room and treats them to a fucking feast. If you and I sat down and drank some fucking tea together on a chilly spring afternoon, we would immediately join each other in a good, neutral space. We’d feel calm and we’d say true shit to each other and we’d also laugh a lot. It wouldn’t be about one person trying to be funny and wise and the other person trying to seem healthy and confident in spite of their shame. We would be two people whose souls matched perfectly, and our truest selves and our purest desires would show themselves. You have to calm way the fuck down to make that happen. You can’t live inside your neurotic mind. You have to follow your body’s wild wisdom and trust it, and you have to look someone else in the eyes and recognize that they’re trusting themselves, too.

That’s a pure connection. And honestly, it doesn’t matter that much if there’s romantic love in the mix — physical attraction is its own odd thing that’s secondary, really, to souls that are attracted to each other. When you have a connection like that, and you notice it, and the other person notices it, that’s the ABSOLUTE BEST, and it matters. It has weight. It has energy. It’s sunshine that you can pull out of your pocket and feel for months afterward.

How do you get there? You build from what’s already working. You resist the defeating dominant stories about who you are and where you are, and you tap into your own private story of who you are and where you are. Here’s the start of your story: You found your fucking power. You’re using it in performances. You’re using it in your new friendships. You use it as fuel to explore the world in ways you didn’t before. The shark knows a few things about what’s good for you, as it turns out. You have the laser focus of a hungry predator. You are a joyful child and circling shark, all in one. You are already loved. You can feel that, right? Your behavior onstage and your honest connection with your kids tells me that YES, YOU CAN FEEL THAT.

You have to keep going to those sources and connecting with your power and storing it up. I want you to let some of your dark emotions drip into that space, too, without allowing so much of it in that you’re overwhelmed. What if you created a new performance that had a tiny bit of your sadness inside of it? It could be a small symbol of mourning for your old life, maybe, or just a little token of your shame or anxiety. Integrate your emotional fears into your power so they have somewhere to live and breathe.

But don’t do so much that it capsizes your whole ship. Experiment with your art.

Try to examine and explore and play with every dimension of your life. Which dimensions of your current look are you struggling with, and where can you try something new? Are there solutions there, with makeup or clothes you haven’t tried, as simple as that sounds? What if you brainstormed some of these small things with trusted friends? Do you need to think through your living space and how it makes you feel? Do you have areas of your life that you avoid because you associate them with rejection, or your past life, or your marriage, or some core shameful part of you that feels intractable?

These things sound trivial, but they aren’t. When you’re adjusting in the wake of a big change, you need to slow down and get very thoughtful about the things that incite your dread and shame. I spent a full hour meticulously washing two windows in my kitchen as I was waiting for what I was sure would be bad news a few weeks ago. I got granular. I used a toothbrush. I am a scrubbing peasant at heart, and I always have been. When I feel terrible, nothing makes me feel better than scrubbing the floor on my hands and knees. I forgot that.

Sometimes you need things that you didn’t realize you needed. Sometimes you want things that you never would’ve imagined you’d want.

But it’s not just the small stuff. The luminous self you become onstage needs to join you in your day-to-day life. Think of your calm performance mind. Think of your open, connected parenting heart. These are the manifestations of your core self. These things are not performative (paradoxically!). Think of how you draw your shoulders back before you take the stage. Think of the peaceful, vibrant energy that washes over you, in that moment.

There’s a name for people who struggle in their efforts to make reality match the colorful and intoxicating worlds inside their core selves: Artists. You need to understand your destiny on this planet as an artist. And I would argue that anyone — I REALLY MEAN ANYONE — creative or not, who feels impatient and bewildered by the drab, passionless, small-talky nothingness of everyday life needs to think of themselves as an artist, too. Impatience and a short attention span often hint that a person has vivid universes inside of them that aren’t getting honored or even noticed enough. But it takes active, thoughtful work to tap into the most robust part of your life and bring that energy to the parts of your life that are lagging behind. It takes focused effort to examine the shame and rejection and fear that loom at the edges of your frame and then invite some of that darkness in so you can address it, and reckon with it, and knead that gloomy magic into the essence of who you are becoming.

That doesn’t mean you have to walk around saying I AM REJECTION ON LEGS, IN A WIG. I AM BUILT WRONG AND DEEPLY UNLOVABLE. Those statements are an echo of how our culture berates us just for being what we are. Don’t listen to those noises unless they amuse you for the comically shortsighted nonsense that they are. Our culture is a fucking ant farm. The trapped ants always, always agree with each other about anyone who is different. What else can they do? Their lives are small and narrow.

Your work as an artist is to create the opposite of those negative statements and those noises. Your story doesn’t slip easily into some dichotomous nightmare realm of feminine and masculine, does it? You can be armed with your fantasies and you can discuss pragmatic concerns with a vast sea of smart friends, but the person you’re becoming slips outside of these flimsy culturally constructed limits, isn’t that right? You’re a complex, contradictory being. How could you reach out to so many rapt, willing audience members if you weren’t? You have layers of wisdom to share with everyone around you. You tap into that fact when you’re onstage. You tap into it when you’re on a walk with your kids. You have to relocate that calm power in your quiet, still moments, and also when you’re fearing silence, bracing against grief, dodging a mountain of shame. You are half-broken and also more robust and resilient than anything an ant would understand. You’ve been seared by the sun but you’re not afraid of heat, not afraid of light, not afraid of brilliance — never, ever! You’re daring and courageous — already, right now, tomorrow, the next day, forever.

Do you know how envious the world is of your power? You do. Because it’s inside your father’s thousands of angry words. Do you know how much love there is for you in this world? You do. You can feel it when you walk onto the stage.

Choose a patron saint. Lately mine is Georgia O’Keeffe. Who took a crumbling house in the desert and turned it into a fucking palace made of empty corners and blank walls and old bones bleached by the sun? Who showed her craggy old woman face and it was the most gorgeous thing anyone had ever seen before, a work of art, enviable, unmatched, untouchable? Do we care what an ant understands about that woman? Or do we want to crawl into her spot of sunshine and live there forever?

Before she takes the stage, Stevie Nicks sometimes whispers, “Walk with me, Prince.” Find a patron saint and ask for their help and guidance. You are not becoming that saint or even emulating that saint. You are asking that saint to walk with you.

Ask open-hearted mortals to walk with you, too. I’m walking with you already. Can you feel it?

You’re in the right place. Construct yourself a narrative that’s buoyed by the power you already have. Build your faith out of the darkness that leaks in when you slow down. Sweep your shame out the door every few minutes. It will come back. Keep sweeping it out. You’re in the right place.


Ask Polly is moving to an every other Wednesday schedule, but there’s a new Ask Polly newsletter to fill in the gaps; please sign up here. Polly’s evil twin Molly’s newsletter is here. Order Heather Havrilesky’s new book, What If This Were Enough?, here. Her advice column will appear here every other Wednesday.

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Ask Polly: ‘I’m Trans and I Feel Unlovable’