Why would a man want to be a woman?

The allure for effeminate gay men to go 'trans'

There’s a scene I’ve watched play out numerous times in my life. It goes something like this: I’m in the breakroom along with a dozen or so coworkers. A woman enters and another woman in the room sees her. She screams out in joy—she hasn’t seen this woman in a while! The other woman responds by screaming in joy too. Oblivious to the rest of the room, they run to each other, hug each other in a tight embrace, rocking and swaying, while excitedly telling each other how happy they are to see each other. 

I have never seen two men do this.

I thought of this scenario when, during a discussion on trans, a woman asked me, “Why would a man want to be a woman?!” My closest friends my entire life have been females, so I understand where the question comes from—basically, women have to put up with so much shit in life, why would a man want to give up all the benefits of being a man and deal with what women have to go through? I won’t say that I have The Answer, but I do have an idea. It occurred to me that it may have something to do with the freedom of expression that women have that men do not. I’m not saying ALL women behave like the scene I described at the beginning of this piece—far from it—I’m saying that women have the option to behave this way. Men do not. Men have to keep their emotions in check.

You may find the kind of behavior between the women I described above as frivolous, ridiculous, undignified, off-putting, but still…there it is. Some people, male and female, like to and want to behave that way. I’m sure they would tell you that’s just the way they are. Some people are exuberant, demonstrative, ‘colorful’, theatrical, emotional. Especially, some gay men.

I think the desire to ‘be’ a woman may stem from this—the freedom to express your emotions openly, candidly, freely, passionately. Men have a much more limited range in this regard. For sure, this is where the appeal to do drag comes from—there is no such thing as an introvert drag queen. And drag is a gateway to trans.

---

Women often reject ‘femininity’, but men cannot in the same way reject ‘masculinity’.

From an analysis on 'femininity' by Women's Declaration International USA:

…in fact we are all subjected to enforced femininity. That said, maybe some of us can choose to reject femininity, at least to some degree, when we are adult women with more autonomy.

I think it can also be said that men are likewise subjected to enforced masculinity. But can men choose to reject masculinity? Safely, among other men? And without crossing the line into misogyny? Where are the lines drawn? How much further away from ‘masculinity’ can a man go until it becomes ‘femininity’?

Much is talked about the ‘performative’ nature of femininity when it comes to ‘transwomen’—and yes, there is truth to this. But this assumes that all men are naturally masculine. If that were the case, then, yes, trans is ‘putting on a show’. But all men are not naturally ‘masculine’, any more than all women are naturally ‘feminine’. So what if you’re a man who has no or very little masculinity? It follows then that a man who has been told (and knows) that he is ‘feminine’ will find our current culture pushing him to adopt a female persona.

I’m not talking about autogynephiles—that is an entirely separate issue that I won’t defend or even attempt to figure out. (For an interesting perspective on that topic, read this PITT article.) I’m talking about effeminate men—let’s be honest, mostly gay men—for whom being ‘manly’ would be a full time effort. If you’re that kind of guy and masculinity doesn’t come naturally to you, then ‘masculinity’ becomes the performance. Or, perhaps, the degree to which you have to enhance your masculinity in order to be accepted in everyday life—your behavior, by necessity, must be exaggerated and performed. (I’m not a flaming queen but I’m also not the butchest dude around. Every time I enter a straight man’s domain—for instance, when I bring my car to the garage to get work done—I watch how I dress, how I talk, how I move…just to feel safe. And not get overcharged!)

There are not too many flamboyant straight guys. That’s why this old Dana Carvey SNL skit is so funny:

Gay men have had to pass as straight for eons—this is accomplished by ‘toning down’ and/or completely suppressing effete attributes. But we have now entered a post-‘gay acceptance’ era in which gay men have gone in the other direction, fully embracing their femininity to the point where they decide to not just pass as, but ‘be’ a woman.

Where I work, I have seen men who (because the dress code has been changed and they are now allowed to) wear skirts, dangly hoop earrings, nail polish, and (one time, strutting through the utilidor) high heels. I think they all look ridiculous and I find it completely unattractive, but that’s just my opinion. Have at it, dudes. But it occurred to me that these are probably gay men who were forced to suppress their feminine sides as kids, and now that the floodgates have been opened, they’re making up for the lost opportunity. Maybe if they had been allowed to explore girl’s clothes, toys, accessories, makeup, etc. when they were little boys, they would’ve gotten it out of their system. I think boys and girls should be allowed to play, pretend, and explore everything. A little girl can wear a tutu and play hockey—at the same time, even! Can we say the same for little boys?

In the adult world, women can complement each other. They can say “I love your hair!” or candidly tell each other how their asses look in jeans. Can men do this in the same way? Any complement about a fellow man’s appearance would have to be followed with “No homo”.

In the workplace, how can a man ‘express’ himself? You get the choice of a black suit or a blue suit. Yawn. And if you’re like me and add in a fun colorful tie just to break the fucking monotony, you get known as ‘quirky’. Even when I lived in Seattle (one of the wokest of the woke cities) for a year back in 2017, several people told me I was ‘too colorful’ with my style. ‘We wear black, browns, and grays here,’ I was told.

---

Women will tell you how difficult it is to be a woman, but have you considered that for an effeminate man, maybe being a woman seems…easier?

As Donovan Cleckley writes:

In my life, my father set a standard of manhood defined by caring for others’ welfare, extended to other animals, persevering in hard but ethical labor, and respecting women and men alike in one’s work. Looking back, I can see the definition of “masculinity,” for men in our household, was not about stereotypes but about virtues, which comes to be revealed as human virtues. A man’s careful regard for others becomes what matters to male selfhood, not his appearance or his interests. From this understanding, I developed a sense of self-affirming being. Over time, however, I learned there were varying definitions of “masculinity,” even “traditional masculinity.” Since the later nineteenth century, for instance, popular definitions have emphasized the man should maintain a mask against the appearance of sensitivity and expressiveness. This fear has to do with being perceived as not being “masculine” in ways deemed culturally desirable for males. Under these conditions, it makes sense for men to exhibit a phobic reaction to perceived “femininity.” Men can become so obsessed with looking manly that it makes them mad.

Men are not supposed to cry or show emotion. I wonder if any other men have had this experience that I’ve had many times in my life: You’re watching a movie with family or friends, and they’re keeping an eye on you. During a sad sequence, they’re watching you for your reaction. “I see you crying!” they point and laugh. You got caught and you are ridiculed for showing emotion. Boys aren’t supposed to cry. We’re taught this as children.

(It seems like the only time little boys are allowed to cry is when they get a puppy…

It’s practically a genre

…at least that’s something?!)

The flip side of this is another scenario, in which you get accused of being ‘stoic’ or uncaring for not responding with appropriate emotion. You can’t win!

As males, we grow up being told that boys and men have to look and behave a certain way. Boys aren’t allowed to like certain colors, toys, or types of play. Boys who are not athletic or into sports are forced to play anyway…and then told ‘you throw like a girl’. There are right and wrong ways to talk, stand, sit, gesticulate, hold a bag.

As boys, we are taught to not be feminine. I’ve written about this previously. As we grow up into gay teenagers and gay men, these thoughts follow us. It doesn’t go away. 

If you think gay men are more open to effeminate guys, you’d be dead wrong. Because so-called LGBTQIA+ groups endlessly yammer on about ‘the Community’, the impression is that there is one big happy family of love and acceptance. This has never been the case. The truth is—aside from maybe the adoration as comic relief in movies and TV shows—feminine gay men are not especially desired or respected. People rarely talk about this homophobia within the gay male world.

I’m sure someone like Dylan Mulvaney had a rough go of it as a frail, flamboyant gay man. He was probably a hoot to hang out with, but maybe embarrassed his friends in public from time to time. We’ve all had a gay friend like that. But as a ‘girl’, he is celebrated. He went from an actor who couldn’t get a break to a TikTok celebrity with a legion of worshiping fans. This isn’t Dylan ‘being her authentic self’; it’s marketing, plain and simple—buoyed by internalized homophobia. In 2023, in the latest example of ‘You Can’t Make This Shit Up’, former gay men’s magazine Attitude¹ honored him with ‘Woman of the Year’.

Why would a gay man want to be a woman? Maybe, just maybe, to be more palatable to the generic public?

In an interview with Rosie O’Donnell², Dylan talks about coming out as gay as a teen, and believing through his Catholic upbringing that being gay was evil. He goes on to describe his feminine behavior:

There was a boy in my school who came out to his parents and said, ‘I'm gay, but I'm not Dylan Mulvaney gay.’ And I thought that was the most offensive thing I'd ever heard, because I was like, I'm not that gay, like what are you talking about? And now I was like, oh, babe, like that femininity that was there that I was like forcing down so desperately was actually just my transness that didn't have like a way to get out.

Here’s Dylan telling Rosie about his frustrations in college as a musical theater major:

I really tried to shed so much of that feminine energy because I would, you know, they train you to be these like ensembles strapping, you know, jocks that can lift girls. And I tried to be that and I failed every time.

It’s called accepting yourself for who you are, Dylan. Yeah, it’s hard and sometimes it sucks. Leslie Jordan, Steven Root, Danny DeVito, Paul Giamatti, Steve Buscemi…none of these very talented actors made it as a leading man. But they embraced their uniqueness and found success. It’s what’s known as being a character actor.

I have read/heard from detransitioners that they were treated much better as ‘transwomen’ than they were as gay men. And I believe it. When a man announces he is a woman, he immediately receives praise and celebration from the ‘LGBTQIA+ Community’. These ‘allies’ believe they are being kind and accepting, and that people like me are ‘hateful’. They’ve got it wrong—affirmation is unkind, and blind acceptance is cruelty.

If only more of these ‘allies’ would ask the question, ‘Why would a man want to be a woman?’ Maybe instead of taking it all as a matter of faith and instantly affirming, congratulating, praising, and celebrating when a man tells you he’s a woman, instead…pause…and ask him…why?

---

I just recently listened to a podcast from the wonderful Stephanie Winn featuring a detransitioner named Levi Hayes. Levi described the shame with being ‘different’ as a boy, and how that affected him as he grew up to be a gay man. This led him to adopt a ‘transgender’ identity for eight years, but he has since desisted. From his Substack:

For many gay men, coping with that shame means not only being closeted but donning a mask of hyper-masculinity to blend into straight society. For others, like me, who couldn’t hide their differences, the world was far less forgiving. My mannerisms, voice, and appearance betrayed me, leaving me vulnerable to mockery. Those of us who didn’t fit society’s expectations of masculinity were often judged not just by straight men but also by other gay men, whose internalized homophobia left them unable to face their own insecurities.

In this interview with LGB Alliance USA, Levi describes the contempt for feminine men within the gay community:

---

We need to make life easier for boys and men to feel free and comfortable to be themselves…however that may be.

I’ll leave you with the wise words of the fabulous, handsome, charismatic, yet not very ‘masculine’ Mr. Menno:

1. Now it’s another alphobedient ‘LGBTQ magazine’.

2. …who should really know better than to promote the homophobia and gay erasure of the trans movement, but, alas, is another brainwashed celebrity.