Somewhere New to Hide

Gender nonconformity and the limits of liberation through identity

Three years ago, I wrote an essay I never published. It began with a deliberately provocative question: Can transgenderism, in some cases, merely be a consequence of sissyphobia?

The wording was intentional. In Black American culture, “sissy” has long been an oftentimes disparaging term for an effeminate man, carrying assumptions about homosexuality along with judgments about his failure to conform to masculine expectations. By “sissyphobia,” I was trying to name something more culturally specific than a general discomfort with gender nonconformity: the particular contempt directed at men, especially gay men, whose femininity makes their maleness socially uncomfortable for other people.

I had been thinking about effeminate men and a contradiction I could not quite reconcile. Our culture was supposedly dismantling restrictive ideas about masculinity and femininity at precisely the same time it seemed increasingly inclined to interpret gender nonconformity as evidence of another identity. A man could wear women’s clothing, behave flamboyantly, reject conventional masculinity, and perhaps discover that these things meant he was not simply an unconventional man after all.

Actor Alex Newell was one of the people who made me notice it.

I had not watched Newell on Glee. I was introduced to him years later through Zoey’s Extraordinary Playlist, where he played Mo, an effeminate, cross-dressing gay man whose gender nonconformity did not require him to stop being a man. Contemporary coverage described Newell as gay, cisgender, and gender-nonconforming. He was male. He was gay. He was feminine. None of those facts needed to cancel out another.

Only later did I learn that Newell had already spent years being asked, implicitly and explicitly, whether that combination was enough.

Newell joined Glee in 2012 playing Wade “Unique” Adams, a character who came to be portrayed as transgender. Newell himself did not identify that way. In 2013, while playing one of television’s most prominent transgender teenage characters, Newell explicitly identified as male and said the role had not changed how he understood himself.

And Newell was aware of the pressure surrounding his identity. In a 2018 interview with Vice, he described repeatedly being assumed to be transgender despite continuing to identify as a gay man. The assumptions apparently became persistent enough that he questioned himself: “You’re telling me that I am, so I guess I am.” He joked about feeling like a “trans poser” and even wondered aloud, “Maybe I should just be trans.”

Those comments stayed with me. Here was an effeminate gay man being told, from several directions and over several years, that simply being an effeminate gay man was somehow an incomplete explanation.

Then, in 2023, something changed. Newell appeared on Broadway in Shucked as Lulu. That spring, he was widely described as one of the first openly nonbinary performers nominated for an acting Tony, and when he won in June, he described himself from the stage as a “queer nonbinary fat black lil’ baby from Massachusetts.” That was when I started writing.

Newell alone knows why his understanding or description of himself changed, but the sequence crystallized a question I had already been asking. I had encountered Newell as a gay, gender-nonconforming Black man who resisted other people’s attempts to interpret his femininity as evidence that he was transgender. Eventually, the culture that had spent years struggling to leave that femininity inside the category of man celebrated Newell as a history-making nonbinary performer.

Why had an effeminate gay man required further explanation?

I returned to essentially the same question from the opposite direction earlier this year in “Girls Are Not Allowed to Be Girls Anymore.” There, I wrote about girls and women for whom femininity seemed to become easier to inhabit once it was separated from womanhood: female people identifying as men or nonbinary could return to dresses, makeup, camp, glamour, and exaggerated femininity and have those same things interpreted as subversive rather than conventional. I wrote then that the performance had not changed…the permission structure had.

Looking back, that essay and my unpublished one from 2023 were describing two sides of the same phenomenon. We were told that gender identity would free people from restrictive definitions of men and women. But what if, for some people, it did something closer to the opposite? Instead of making the categories wider, it provided an explanation for why people who did not fit comfortably inside the stereotypes might belong somewhere else.

The feminine man need not expand our understanding of men. The masculine woman need not expand our understanding of women. Human variation remains exactly where it was; we have simply developed new terminology for moving some of the people who embody it outside the categories they complicate.

And perhaps nowhere is that contradiction more apparent than in sexuality.

I was reminded of this recently while listening to a viral clip of a discussion on The Joe Budden Podcast. The panel was arguing about how to describe the sexual orientation of a man who dates transgender-identified males. Marc Lamont Hill argued from the premise that transwomen are women: if a man dates women, including transwomen, he can still describe himself as straight. Others in the room returned to the distinction Hill’s framework deemphasized: whether sexual orientation concerns the sex of the people to whom someone is attracted or their gender identities.

The exchange interested me because it exposes something about gender identity that receives less attention than pronouns or bathrooms: it can also provide a conceptual escape hatch from homosexuality. If a man can have sex with another male while preserving a heterosexual identity because that male identifies as a woman, he does not necessarily have to ask himself what attraction to another male means about his sexuality. Nor do the people around him necessarily have to reconsider how they understand him. A male friend uncomfortable with homosexuality can continue regarding his friend as straight because gender identity has transformed a same-sex relationship into an opposite-sex one without changing the sex of either participant. Gender identity can answer the uncomfortable question for everyone before anyone has to ask it.

Which brings me back to the “sissyphobia” I was trying to describe in 2023. Homosexuality was always embedded in it: contempt for the effeminate man has long been difficult to disentangle from discomfort with homosexuality. Perhaps gender identity did not create either discomfort so much as provide a modern vocabulary through which older ones can survive.

We no longer have to tell the feminine boy that he should toughen up and act like a man. We can affirm his femininity while entertaining the possibility that it means he isn’t one. We no longer have to tell the masculine girl that she needs to behave like a lady. We can celebrate her rejection of womanhood instead. And we no longer have to tell a man attracted to another male—or ask the people around him to accept—that he may be homosexual or bisexual. If the other male identifies as a woman, we can preserve heterosexuality by changing the category of one of the participants.

The language is different from what previous generations used. The underlying discomfort may not be.

That is why D. Smith’s announcement last month caught my attention. After years of publicly living as a trans-identified male, Smith announced that he will now live as a man and use he/him pronouns. One person’s decision cannot explain anyone else’s, and I have no interest in supplying Smith with motives he has not supplied himself. But I found myself thinking again about permission. What if a feminine or gender-nonconforming man can increasingly imagine another possibility…simply being a man?

Comedian Flame Monroe makes that question even more interesting. In 2019, while publicly identifying as transgender, Flame described being part of the LGBT community “only four hours a day,” when “the check” was involved, and elsewhere put it more plainly: “I am somebody’s daddy. This is my job.”

Earlier this year, Flame declared, “I ain’t even trans no more. I don’t even identify as trans.” More strikingly, in the same conversation Flame asked what had happened to tomboys and “little feminine boys,” arguing that being masculine or feminine should not automatically mean someone must be transgender.

Newell, Smith and Flame have taken very different paths, and none can explain the others. But together they illustrate how unstable the boundary between gender nonconformity and gender identity can become when the culture surrounding both changes.

Whether unconventional gender identities are actually declining matters less to me than what changing identities reveal about the role culture plays in how people understand themselves. For years, increasing LGBT identification among younger people was frequently explained through greater acceptance: people who had always existed finally possessed the freedom and vocabulary to identify themselves. There is surely some truth in that explanation. But culture does not merely give us words with which to describe ourselves. It can also influence which explanations of ourselves seem plausible in the first place.

By 2025, in “The Trap of Trans Activist Victimhood,” I was asking the other half of the question: not what makes someone enter an identity framework, but what can make it difficult to leave. Now I find myself wondering what happens when the surrounding culture changes enough to make another path visible.

The question is no longer simply whether people can leave transgender identities. It is whether we can build a culture in which fewer people need an identity to explain their nonconformity in the first place. That requires something more radical than another collection of labels. It requires making what comes to mind when we hear man and woman, bigger.

Men and women can be masculine or feminine, homosexual or heterosexual, bisexual, flamboyant or reserved, glamorous or androgynous. None of those characteristics changes their sex. That was supposed to be one of the liberating insights of rejecting sex stereotypes: personality does not determine sex. Somewhere along the way, we began treating personality as evidence of identity instead.

Perhaps D. Smith represents nothing beyond D. Smith, but the possibility that interests me is not whether more people adopt or abandon transgender identities. It is whether the permission structure changes again.

That a feminine boy does not need an explanation for his femininity. That someone who experiences same-sex attraction can confront that attraction without needing another person’s identity to convert it into heterosexuality. And that someone who once understood himself through gender identity can eventually say, without shame or political significance, that he understands himself differently now.

My unpublished essay in 2023 asked whether society’s discomfort with effeminate men might sometimes contribute to transgender identification. Three years later, I think the better question is broader. Did a movement that promised freedom from restrictive ideas about men and women instead give those restrictions somewhere new to hide?

If so, liberation does not require another identity. It requires restoring something much simpler…enough room inside man and woman for human beings to be complicated.