Apr 16 • 13M

The Best Kind of Midnight Conversation

It's tough to create space but magical when it happens.

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Charlotte Clymer is a writer and LGBTQ advocate. You've probably seen her on Twitter (@cmclymer). This is the podcast version of her blog "Charlotte's Web Thoughts", which you can subscribe to here: charlotteclymer.substack.com
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(Getty // Credit: Tzido)

Friends, with few exceptions, this has been an especially awful month in an especially awful year, particularly for the trans and non-binary community.

I will admit to y’all that I have been quite depressed in recent weeks—certainly more anxious than usual—in response to the avalanche of anti-LGBTQ actions we’ve seen across the country, with an emphasis on trans and non-binary children.

In times that are particularly difficult and draining, I find it’s helpful to remember those moments when things go right, when understanding is sought and achieved, when there’s an important bridge built between different perspectives.

Several years ago, it was late night in D.C, and I was walking past this random building downtown on the way to the Metro.

A security guard happened to be standing outside. He called out to me.

"Excuse me, Ma'am? I don't want this to come across as rude, and please forgive me if I'm overstepping my bounds, but would it be okay if I ask you a question?"

As you might guess, this is a rare occurrence. In my experience in the District—and I imagine it’s this way for most big cities—when I’ve walked past a security guard stationed outside, we may exchange a “good morning/evening” but that’s it.

So, yeah, I’m a little skeptical. And I feel like I know what’s coming. And I’m right.

"That depends."

“I get that. Hear me out.”

It turns out he's a grizzled old Army veteran who was turning 50 the following month and now worked in private security. And yes, he has questions about what it means to be transgender.

I am not exactly thrilled by random questions from strangers about my gender identity in social settings like parties or professional events—let alone on the street—because they're not usually asked in good faith. Also: it can suck to meet strangers who zero-in on letting you know that they know you’re transgender.

(Please avoid doing that. Seriously. If a trans person wants to talk about being trans, they’ll let you know.)

But this gentleman was otherwise so very respectful and seemingly earnest in asking that I felt compelled to answer, and I'm glad I did.

We proceeded to have a 90-min long Q&A about assigned-sex-at-birth, sexual orientation, gender identity, and gender expression and how all these things are separate aspects of a person and shouldn't be conflated. I gave him Introduction to Gender & Sexuality in 90 minutes.

Yes, 90 minutes. I can’t quite believe it, either. For an hour-and-a-half, it went by pretty quickly.

He wanted to know all the terms so he wouldn't get them wrong. He had all these questions--all respectful--about what this or that means. He was a very eager student who really wanted to understand all of it. He had a rare good faith curiosity about him.

In that moment, I remember being impressed and also: how sad was it that I was impressed?

We then talked about the Army and he was taken aback when he learned I'm infantry. It hadn’t occurred to him that an infantry soldier, a profession he greatly respected, could be transgender. It wasn't disrespectful; it was more revelatory for him. He somehow hadn't considered this before.

And then, he requests to ask a “delicate” question. I said “sure”, and that's when he hits me with this:

"I've just been wondering, lately. I love women, but sometimes, in the back of my mind, I wonder about men. Is that weird?"

It’s never surprising to me that a straight cis man has thoughts outside of the strict binary prescribed to them, or rather, forced on them. That’s completely healthy and normal. It’s a very human thing to question oneself, even—and especially—if that results in greater confidence in one’s perception of themself.

If a straight cis man becomes more comfortable in his own skin through that kind of self-assessment, regardless of result, isn’t that a win for everyone?

Judgment derives from insecurity. The oft-occurring snap response to homophobic men is that they must be in the closet, and that’s why they’re so insecure.

I’m absolutely certain that’s true in many cases, but it fails to account for heterosexual, cisgender men who are quite concrete in their own identity but lash out at LGBTQ people because our mere existence messes with the arithmetic that struggles to justify their superficial and unsustainable understanding of the world.

They believe our existence implies an extraordinary labor for them. We are an annoyance and disruption to their seamless, gendered glide through society. There are many straight cis men who find considerable comfort in the “men are men, women are women, men should only have sex with women” mindset because it makes everything simpler.

It justifies a whole range of gendered obligations and provides—in their own minds, at least—a rational blueprint for behavior, no matter how reductive and flawed and oppressive. Surprise, surprise, indeed, that highly gendered dynamics are easier to accept when one is placed at the top of the hierarchy constructed by those dynamics.

Anyway, back to our friend.

On the few occasions when I’ve had conversations like this, there’s a striking vulnerability emphasized by presentation. This gentleman looked like a typical middle-aged dad (indeed, he had two grown kids). He had a trimmed mustache, close-cropped hair, and a “good enough for the evening shift” jacket-and-tie uniform.

I could easily see him being a high school history teacher or the guy on the block who hosts neighborhood barbecues or the deacon at church who laughs a bit too much during worship. An all-around solid human being who has frailties and a particular gift for showing up with the right words of encouragement when needed.

And so, we talked at length about how human sexuality is complex, and I assured him his feelings are completely healthy and certainly not definitive, but if they were, that's okay, too. That he didn't have to put himself in any sort of box. He just has to respect how others define themselves.

He got it. There was a real understanding achieved. He seemed so relieved by all of this, like an enormous weight had been taken off his shoulders. He had been struggling with these feelings for so long and didn't know who to talk to or what exactly to ask. He thanked me at the end of our conversation. He clearly felt so much better.

I wound up missing the last Metro of the night and took a rideshare, which was completely worth it.

That evening has made think so often about how I wish good faith being present in these discussions were a given and not a novelty — how our differences could inspire unity, not dissolve it.

This isn’t to say that, if you have questions of your own, you should be reaching out to the queer folks in your life, let alone strangers, for some tutoring on gender identity and sexual orientation. That’s not their job. If they offer space for that kind of conversation, wonderful, but it’s not their responsibility. Respect that boundary.

Instead, take it this way: all that shame and hurt you have inside? All those questions that eat away at you, the ones you’re afraid of asking because you’ve been told they should feel out-of-place by conditioning in a society that says your healthy and normal questioning is wrong? All those self-critical thoughts you have are unnecessary.

If you see yourself, however little, in this gentleman, let me assure you of something: you deserve a hell of a lot better than how you’ve been forced to settle. You deserve love and understanding. You deserve to feel authentic, and you deserve the freedom to define your authenticity on your own terms.

Again, that doesn’t necessarily mean you’re LGBTQ. It might, and if it does, that’s great, but it can also just mean you’re finding comfort in your own skin, however that may look, even as a heterosexual and cisgender person.

People who embody anti-LGBTQ views have failed to appropriately negotiate the discomfort that’s motivated by an awareness of their own incongruence between the selves they’ve constructed with arbitrary standards and the opposing nature of the changing world around them.

Shorter: they need others to act exactly as they do to feel truly secure in their worldview. They constantly seek affirmation that they’re traveling the right path by attempting to force everyone else to travel that path, too. In their minds, their worldview can only truly exist in the absence of opposing worldviews.

They’re completely responsible for their hateful views, and also: I genuinely feel sorry for them. Imagine being that controlled by one’s own insecurity. What a terrible waste of one’s own precious, limited time on this earth.

On bad days in the world of LGBTQ advocacy—and there are a lot, lately—I think of that gentleman who had the courage to be vulnerable and ask himself if he deserves the authenticity he’s always wanted but never sought to understand.

Until that evening.

I pray that more follow him.

Hey, friends, quick note: this is my main source of income. It’s how I pay the bills. I would love if you could support my work with a paid subscription. It would mean a whole hell of a lot.


Hi, I’m Charlotte Clymer, and this is Charlotte’s Web Thoughts, my Substack. It’s completely free to access and read, but if you feel so moved to support my writing, please consider upgrading to a paid subscription: just $7/month or save money with the $70/annual sub. You can also go way above and beyond by becoming a Founding Member at $210.