A few years ago, when I first started this writing project, I wrote an essay about men and my own relationships with men, one year into being poly with my wife. It was, to put it mildly, heartfelt but horrendously cringeworthy, mostly due to the sheer amount of romanticization of the interactions I had with the men I was sleeping with and dating, and how I treated what should be bare minimum behavior (such as not making me feel disrespected for being trans) as something to be applauded and placed on a pedestal. I remember reading it a few times aloud at various events and parties. I can still remember the look of confusion on people’s faces—objectively, I can say I was looking at dating men through rose-tinted, post-transition, second-adolescent trans-girl lenses, and it was everything a modern woman in 2026 is told not to be—pick-me, validation-seeking behavior. And the truth is, I was definitely leaning heavily into pick-me territory, and you know what? Why wouldn’t I have?
When I was growing up, I didn’t feel even remotely “attractive,” and I’m at peace with that. It’s hard to find yourself attractive or even desirable when you don’t like what you see in the mirror on a foundational level—the world saw me as a gay Asian twink, and that’s what I saw too, and I didn’t like it. And the men who did like me were not the men I wanted to like me—primarily creepy white dudes with yellow fever who got off on the idea of railing a femboy Asian twink. I wanted the hot straight guys I met on my nights out in the East Village to rail me, to talk to me the way I saw them talk to my straight girlfriends—all the dating clichés that so many women genuinely (and rightfully) loathe, because what I looked at with envy was probably borderline harassment for them on a daily basis.
But that’s the thing with desire—we can desire things, interactions, relationships, even if we know they’re fundamentally incompatible with our own desire for a healthy relationship with our inner self. I loved when guys would mistake me for a girl, but my heart would drop the minute I told them I was “gay” (which was a lie—I was just deep in the closet about being trans), and the look of disappointment (or even disgust) I’d see wash over their faces would absolutely kill me. And on the rare occasion that I hooked up with or dated a cis straight guy, it was never how I wanted it to go. It was less “let’s go to a fun cocktail bar and talk politics,” and more “hey, my roommate’s out, come by, but be discreet—let’s not talk about this and just keep it on the down low”—existing as a secret, something they simultaneously wanted to fuck, but were also ashamed of wanting. It sucked.
And mind you, this was all happening when I was between 18 and my mid-twenties (when I decided to transition), and the world was not what it is today when it comes to trans visibility and conversations about queerness. Back then, we didn’t have terms like heteroflexible, “queer” was still largely a slur, nobody called themselves a doll, transsexual was largely outdated (yet having a resurgence in 2026), “tranny chaser” was a serious way to describe a guy who exclusively dated trans women, “tranny” was still a slur, gay men would text girls “get off Grindr you tranny,” the chasers hadn’t rebranded themselves as “gynosexual” or “trans-amorous” yet, and nobody asked for pronouns in public spaces. Most importantly, the easiest way to explain being trans was by saying “I’m a girl trapped in a boy’s body”—not “sex and gender are different things, and gender exists on a spectrum.” I sound like a bitter old millennial when I say this, but the Gen Z dolls do not know how much better they have things today compared to when I was coming up as one of the goerls—and I promise, this ties into the topic of men too.
So when I did transition, about one year later, everything in my life shifted. From a cultural perspective, it felt like a trans renaissance—Kim Petras was blowing up as an artist, Caitlyn Jenner had won woman of the year for some sports magazine, her show I Am Cait featured some of the US’s leading voices on trans discourse discussing real sociopolitical issues on E! Entertainment, Pose was raking in accolades for featuring Black and brown trans stories, RuPaul’s Drag Race was finally allowing trans women not only to compete but also highlight trans stories, Condé Nast had just launched their new LGBT publication them, and trans medicine was being made accessible on a level never seen before in Western history.
And for a young trans girl who had finally taken the plunge to live a life she actually wanted, it felt like I was getting a second chance at life—especially with men, because for the first time, I felt pretty. Best of all, all the men who I used to wish would just not be ashamed to hold my hand were suddenly telling me I was beautiful, going on dates with me that would make most of my former girlfriends jealous, and agreeing to date me on my terms, not their terms (by then, my wife—then fiancé—and I were already open, but not poly). And as the years went on, my body changed, my life experience as a trans woman deepened, and my relationships with straight and bi men began to feel like an alternate universe compared to the reality I’d known just a few years prior.
By the time I turned 30, five years into my transition, the little gay twink I once knew was nowhere to be seen. Five years of intensive hormone therapy gave me 34B breasts, a 27-inch waist, 30-inch hips, the softest skin I’d ever had, thicker hair, a face completely reshaped by fat redistribution, and most importantly, a half-a-million-dollar pussy from one of the East Coast’s leading gender reassignment surgeons, modeled after one of my favorite porn stars, Asa Akira (I literally told my surgeon, I want a porn star pussy—no flaps, no fat folds, just a flat mound with a clean slit down the middle, and a slit that’ll still get me off—and lucky for me, that man delivered). Not only did I pass, but I was pretty. I’d never felt pretty.
Yes, we can all feel pretty from our own internal validation. Still, I’m not here to bullshit anyone—a large factor in feeling beautiful was that, for the first time in my life, the men who had rejected me throughout my adolescence and twenties, the same archetypes of men who had made me feel defective, were suddenly kind. No—I should say, they were kind to me before they fucked me, after they fucked me, and even after we decided to stop being romantically or sexually involved and just remain friends. That was wild to me. They were sympathetic to my experiences pre-transition; they told me how cruel my ex-boyfriends were, how happy they were that I had a wife who loved me, how I deserved more kindness in my life, and that they were just happy to be around me.
It’s also important to note that I wouldn’t have been ready to accept this shift if I hadn’t experienced the love my wife showed me throughout the early years of our relationship—she taught me not to accept the bare minimum, whether it was from men or women, trans or cis, queer or hetero. I can’t write about my relationship as a bi trans woman who dates cis men without reflecting on my own views on relationships as a married woman. I always say the reason I married my wife was that, pre-transition, she was the first person who was genuinely proud to be seen in public with me, and I knew I’d met my future spouse a month into knowing her.
Since pursuing polyamory with my wife, I’ve dated well over 30 men in the span of three years—some of whom remain beautiful, fleeting memories intertwined with my internal mythology of New York City, some serving as reminders of the kindness I was owed and later repaid tenfold, some acting as reminders that even though many men can be genuinely beautiful souls, many are still predatory and will hurt you if you let your guard down, and some becoming inseparable anchors in my life that remind me life is beautiful because you never know who you’ll meet—and all it took was matching with a hot guy on Feeld or Hinge to do so.
In that same span of three years, I’ve had ex-boyfriends I cried over for years, ex-boyfriends who’ve traveled across state lines and country borders to see me, ex-boyfriends who’ve become important friends I’m unapologetically intertwined with because, for a brief moment in time, they truly saw me. And of course, former boyfriends who’ve become former girlfriends, forcing me to confront my own sexuality on an entirely different level.
In those three years, I’ve also made platonic friendships with a handful of men I met off dating apps—all of whom are my type (what can I say, I’m a flirt, I like being surrounded by handsome men), all of whom, in one way or another, taught me about my own worth—not just in relation to desirability, but in relation to kindness, to being a person, a woman, a trans woman, and maybe most importantly, a proud self-identified slut.
When I first transitioned and felt attractive, I leaned into my newfound fuckability and ran with it—using that revelation as both empowerment and a crutch. I thought to myself, these men no longer treat me as a secret, someone to be ashamed of being seen with, so I shouldn’t take my newfound sex life for granted. But at the same time, I was terrified I would lose that desirability too—so I had a lot of sex, not always because I wanted to, but partially because I believed my connection with these men was conditional.
Put out, or get put aside.
But I was no longer 22, and the men in my life now were not the same men I had met in my early twenties.
Some of the men I trust most today were former dates I met online—men who, after a single date, sent me some version of “you’re great, I loved spending time with you, but I’d rather just stay friends.” Initially, those messages were jarring—not because I was upset about not dating a cute guy, but because I interpreted them as rejections of my personhood. Maybe I didn’t pass enough. Maybe they were secretly transphobic. Or worst of all—the ultimate trauma flare—maybe I wasn’t fuckable enough, and hadn’t put enough work into being the woman I wanted the world to see me as.
I could feel my brain spiraling over the one thing women, especially trans women, tell ourselves not to do—judge our worth based on a man’s approval. But words are easy to say, to read, to ponder—they’re much harder to actually digest and manifest. And I’m going to say another thing we’re not supposed to say: sometimes, you can’t just heal on your own.
Why are we so forgiving of people who say they need closure from bad breakups, yet dismissive—even mocking—of women who need closure from how men have treated them? We allow people to say “my new partner taught me how to see myself as [blank],” yet it’s waved off as superficial when I say I healed my trauma surrounding men by surrounding myself with men.
Because these men who turned me down didn’t disappear, nor did they ever make a move on me, even when the opportunities presented themselves.
I remember an early hangout with one of them—weekday drinks in Paris. It was casual but memorable, like those fun summer nights you remember with new friends from a party. Midway through, it started pouring—the kind of Paris rain that makes you think the Seine might flood—and I realized I didn’t have an umbrella and it was freezing. As I was panicking, he asked if I wanted to go to his place to wait out the rain.
And if you’ve dated men, you know that’s never what it means on a surface level.
When a guy asks you to come over in the rain, it usually means one thing: you’re getting fucked.
So I went, curious to see what would happen.
Imagine my surprise when he literally meant, “you can wait out the rain at my place,” because all we did was sit on the floor, talk about his career, my former career, our creative aspirations, our personal histories, while the rain pounded against his windows and cigarette smoke drifted into the night. He didn’t touch me. He didn’t flirt. He didn’t even make consistent eye contact. We simply sat as friends and existed.
It was beautiful.
And months later, after more hangouts, I realized that he genuinely just enjoyed my company—and I could still be my whore-ish self around him without ever worrying that the relationship was conditional on whether or not we fucked.
When I first started dating men post-transition, I believed that men were only kind to me because I was pretty. They wanted to fuck me, so I leaned into that dynamic because I didn’t want to lose a kindness I had never known before. But through reclaiming my relationship with being a slut—while also healing from the ways men had hurt me—I learned that some men just genuinely like my company and don’t give a shit whether we fuck or not.
I probably sound insane admitting this, but after so many years of conditional friendships with men, you can see how my trauma shaped my views on man–trans girl dynamics.
I love my ex-boyfriends. I love my former lovers. I love my guy besties. I love them all—for teaching me that I deserve to be treated with kindness and respect, no matter how fuckable I am or not.
Do I thrive off male attention? Absolutely.
And I won’t apologize for it—especially when my own views of femininity, self-actualization, and self-healing have all been so deeply intertwined with my relationships with men.
I think the truth is I’ll always crave male validation, and I’ll always view my own femininity in relation to how men see me. But it’s become less about whether or not men in my life want to consume me, and more so if the men in my life give me the space to be every rendition of my femininity, projected desirability, sexuality, and personhood as a trans woman without putting in input on how they think I should or shouldn’t be a woman. I’ll always want to be surrounded by men, and I’m grateful to have a community of men who gave my best interests at heart. These men have my back metaphorically, and some have had their hand on my lower back while pressing my face into a pillow, but both versions of these relationships have one thing in common: I don’t feel used, and nor do I feel a need to perform a version of myself to keep them in my life. And for the first time in my life, I think I’m learned to enjoy being around men in a healthy way, versus in a dependent way.