Being the Big Sib

How to mentor gender questioning people safely

Foreword: This article speaks about sex and kink frankly, but not explicitly or in detail. It’s not appropriate for minors, and should not be read by anyone under the age of majority.

A couple of years ago, I was haunting Reddit, as I often do. /r/asktransgender, in particular, has been a touchstone for me for years. While I was early in my transition, the place was an absolute lifeline for me, allowing me to quietly, as a lurker, find answers to the million and one questions I had when I was starting out. The simplest things—how to hide beard shadow, how to style an outfit, all the basics. And then, as the weeks turned into months, I’d notice people asking the same questions I had wondered, so I started answering them.

It was COVID. I was teaching online. I had downtime between classes.

I was, maybe, four months into my own transition—barely out of the closet—when I got my first direct message from someone who was questioning their gender and had seen something I’d written. She’d posted a thread, I’d responded, and things migrated to DMs as she had question after question for me… and then she faded away, the throwaway account abandoned.

So began a long series of questions, answers, and private conversations, which has never really stopped since. I fucked up plenty of times along the way, learning hard lessons as my attempts to help sometimes did more harm than good. The people involved rotated as time passed, but the questions? They’ve stayed the same.

About a year after that first message, I’d well and truly settled into the rhythm of questioning and answering. One day, someone posted a thread asking about kink and gender, one of the most common questions that gets asked. It’s no real surprise; the shadow that Blanchard casts is long, deep, and has hurt many of us. This one stood out to me, because it was wondering whether futanari porn—don’t google that if you don’t know what it is—was the reason the poster didn’t have bottom dysphoria.

It wasn’t. I won’t hold you in suspense. Then again, this anecdote isn’t about her anyway.

I dropped in with a simple counterproposal: What if, I wondered to her, she’d gotten into that kink because she was a trans girl without bottom dysphoria. If, in short, she’d gotten the cause and effect backwards. After all, the whole premise of porn, and why people seek out such a wide variety of it, is that they want to see themselves in it. It’d make perfect, rational sense to be drawn to depictions of women that looked a fair bit like what her subconscious sense of her gender said she should look like.

After all, I said, if the porn a person consumed could change their dysphorias, then conversion therapy would work, and we know it doesn’t.

In the replies to that comment dropped a single-line reply from a shell-shocked lurker. That, she said, had given her something to think about. I invited her to reach out, and we wandered off to DM’s shortly. Like many of the people I’d talked to before and more since, she was scared of her past, more afraid of her future, and desperately, desperately out of her depth. We chatted back and forth for a few months—her trying to navigate some very understandable fears about her visibility at work, while I tried to reassure her just how little most people would actually care in a negative way. Baby steps, but steps she was eager for, despite her fear.

The thing was, this girl happened to be local. Eventually, we met up, and I dragged her to a local trans support meetup.

This girl, who became my friend by bits and bobs, finally took the step of coming out publicly after more than a year of worry and hesitation and very, very careful planning, and the months following was like watching a caged bird take flight. She spread her wings and soared, almost as if every inch of her new life was an instinct as deep as the ocean.

Of the hundreds of questioning trans folks I’ve talked to over the years, she’s one of only about seven who’s become a real friend.

Being there for the hatchlings

Here’s a truth they don’t tell you when you come out: just by being out, you will, eventually, be approached by someone questioning their gender. It’s an inevitability, in my experience. The authenticity you radiate just from existing, publicly, as yourself, will draw people with that burning, hopeful question in their hearts as if the two of you were magnets.

But then you’ve got to deal with this person—maybe a friend, maybe a stranger—suddenly being right there, on your proverbial doorstep, needing to unburden their soul to you.

One of the most basic truths I’ve come to in my time in transition is that each of us has a responsibility to the people who are questioning their gender. Many of us, whether we knew since we were tiny or never suspected a thing until we were well into our adulthood, would never have had the ability or the confidence to enter the transitions which saved our lives and made them worth living without the kind ear and patient heart of someone who walked this path before us. All of this—realizing a trans identity, entering transition, coming out, any of it—it’s just too much for anyone to do alone. Overwhelming doesn’t even begin to describe it.

At heart, that’s why Stained Glass Woman exists: so nobody feels alone, or forgotten, to the best of my ability.

This article is going to be a little different from most of the articles I write. It is, fundamentally, advice, from my experience helping those I’ve been able to help, and from the mistakes I’ve made along the way. Where I can, I’ll supplement that advice with science, but trans folks helping people to step into their trans identities isn’t something that’s really been studied.

It’s the small, but vital, gift we give each other.

My rules for the gentle handling of eggs

Like anyone, I hold myself to a few rules when I try to help folks out, and I do it because there’s really, really good reason—both in my own experience and from the experiences others have shared with me—that breaking any of these rules can really hurt someone… and while that someone is usually the person reaching out to you, it can be you too.

If you’re going to help someone, know your own rules. If you’re not sure what they should be, consider the ones I use, at least as a starting point.

Rule 1: Follow the Egg Prime Directive

Never, ever tell someone what you think their gender is, or whether you think they’re cis or trans. Not even when you’re absolutely sure. There’s two incredibly important reasons for this:

1. A cracked egg dies. A hatched egg lives. Denial is a tool for survival—it’s a psychological defense mechanism we shield ourselves with when knowing the truth would be existentially dangerous. Forcing that knowledge on them, overwhelmingly, either pushes them even more deeply into the closet or exposes them as a marginalized person in an unsafe living situation. Either way, they will be severely harmed. And yes, there are a few people out there who would’ve been helped by someone just telling them, but they’re the minority—and even if they weren’t, basic principles of harm reduction make it clear that a light touch is the most ethical way.

2. Assigning gender is the tool of our enemy: cisheteronormativity. A gender questioning person is in a vulnerable state of identity reassessment, and insisting on something can harm them in big ways. For just one example, look at the 2022 US Transgender Survey—only 8% of respondents were nonbinary transfeminine people, compared to the 30% of respondents who were nonbinary transmasculine, a difference of 22 percentage points. Trans women, meanwhile, outstrip trans men by ten percentage points. How many transfeminine nonbinary people have either been shoved back into their gender assigned at birth or into a binary identity that fits poorly because of the overwhelming narrative that to be transfeminine is to be binary? For a hatchling’s realization to be genuine, for it to stick, it must come from within.

Don’t crack eggs. Build nests. Help a person find safety and they’ll hatch when they’re ready.

Rule 2: Never accept compensation of any kind

This rule is something I pull from psychology ethics, and for the exact same reason they have it: when you help someone past a major emotional thing that’s hurt them, doing so means they’re in an incredibly vulnerable position, and when they make it, they tend to be extremely grateful. If there’s a monetary or gift-giving relationship there, it can, and usually does, become inherently manipulative. This is why Stained Glass Woman is and will always remain free, and why I have no Patreon or any other form of being financially supported by the people who read it. There’s a lot here that people have used to figure out themselves, and if I held my hand out, even passively, many people would feel compelled to give. That compulsion is never okay.

We give freely what no amount of money can ever purchase. That’s the only way it works. If and when they want to demonstrate their thanks, tell them to instead pay it forward: help someone who eventually comes to them, looking for help, and don’t ask for compensation.

Now, for clarity: I’m talking about one-on-one mentorship here. There are a lot of trans creators—Jammidodger, for instance—who do some incredible mass-education, and it’s perfectly okay for folks like him to sell merch and monetize his videos. When it’s a personal situation, not a parasocial one, is where things get ethically dodgy, and I do a lot of one-on-one mentorship.

Rule 3: Point them towards gender therapy and local support groups

You are not a therapist. Well, unless you actually are a licensed therapist. But most of us aren’t.

I’ve talked about this a lot before, but for a person to grow up and not know about or not act on their trans identity, there are almost always going to be other things going on: abuse, trauma, neurodivergence, and/or many other possibilities. The people you’re talking to are going to need help working through that stuff, because when the gender denial clog goes, everything else tends to start flooding out.

An amateur can do a lot of harm even when they mean to help.

And intending to help doesn’t make things one iota less awful when you do hurt someone.

Rule 4: Know your own boundaries, and stick to them

If you’ve ever worked in a helping profession—teaching, nursing, therapy—you’ll know that there’s always an urge to give all you can to help other people, because it feels so good to see them thrive… but that giving and giving and giving without limit will inevitably leave you a hollowed-out, empty shell, unable to keep helping. We all need a bit of personal space, of quiet, of privacy, to be able to care for ourselves too.

It’s a smart idea to think ahead of time: what are the things I want to keep for myself, because they’re special to me, because they’re private to me, or because I don’t feel comfortable with other people knowing these things? For instance, I don’t ever talk about what’s going on with my pelvis, and I will never. Ever. Maybe it’s the demisexual in me, but I don’t want anyone except my wife and my doctor to know what’s going on down there.

Thing is, when you know your own boundaries and people ask about stuff related to it, you can connect them with other things to support them. When someone asks me about genital stuff or bottom dysphoria, for instance, I can link them to data from the US Transgender Survey or stories from other trans folks who are cool with other people knowing what’s up in that area.

Rule 5: Watch for people who are emotionally self-harming, and disengage if they’re stuck in a cycle

This is the tough one.

Rule 1, above? The whole, “let them stay in denial until they’re safe and ready to realize on their own?” What happens when someone hatches before they’re ready?

Usually, they need to find tools to keep themselves in the closet, because coming out would mean death, abuse, or homelessness. And the most common tool people use, by far in my experience, is emotional self-harm. They’ll latch on to you, often give you some absurd reason they can’t be trans or ask you to disprove such a reason, and then go on and on about how awful of a person they are and how they don’t deserve transition, happiness, their relationships, and so forth, relying on you to soothe them. When the exchange is done, they can leave knowing a smidgeon of acceptance, which gives them the hope to continue the cycle, but having deepened the self-harming behavior that they’re using to hold themselves in the closet.

You cannot help these people. Trying will only ever hurt them, and you, more.

The only thing that’s safe to do is redirect them to gender therapy and local trans support groups, because the support they need to get in order to move forward is delicate and complex. They will usually resist this with every excuse, both realistic and unrealistic, they can find because, again, the objective for them is to keep themselves closeted. They know that, with expert-level support, they can move beyond where they are, and they desperately do not want to.

They are a crisis above your level of expertise.

Rule 6: Meet them where they are, not where you wish they were

At heart, I’m a writing teacher. That’s my day job, and it’s something I love, and the first and most fundamental rule of instruction is to meet students where they are. It’s a guideline that’s worked really well for me in helping questioning people. We have a lot of assumptions of what people know or should know, and what we think in those areas are really hugely affected by the fact that we’re all experts in gender.

We kinda have to be. Becoming an expert is kind of a big part of figuring out a trans identity and transitioning. This stuff’s hard.

It can be really, really easy to forget that between what we know about gender and what cis people generally know, there’s a huge gray space of partial, hodgepodge knowledge. Generally speaking, when someone comes to you for help with their gender, they’ve got some bits and bobs. Some will be right. Some will be hilariously wrong—for instance: a lot of questioning AMAB folks will have picked up things about autogynephilia, a sexist and repeatedly-discredited theory. Your job is to help them fill in the blanks, and correct misinformation.

Most importantly, when someone approaches you for help questioning their gender, especially if they’re a stranger or a passing acquaintance, remember that they already know and answer to the one big question: whether or not they’re trans. They’re not really there for the education, as much as they need it, and as much as that education will help them verbalize their truth.

They’ve come to you because they need to be told it’s okay for them to be trans.

Rule 7: Give them permission to be who they want to be

Because of that truth, remember that your most essential role in helping these people is the same as the first ethics rule the APA expects its licensed psychologists to follow: believe what they tell you, affirm their feelings and right to feel them, and most of all, give them explicit permission to be trans in whatever way feels right or joyful to them.

And they’ll usually tell you pretty quickly what it is that they feel like they are. As I’ve said, they know their truth by the time they find you and the courage to ask. Usually, they’re just afraid of the consequences of it. The single most useful phrase I’ve picked up in talking people through their questioning is this:

“If you want to be a [gender], you can just be a [gender]. You’re allowed.”

You’d be surprised at how many people just need to hear that one line.

Rule 8: Ask more questions than you answer

While there are a lot of answers we can, and do, give when we’re helping a questioning person, mostly what you need to do is ask them questions about how they feel, why they think it is, and ask them to reread their own responses. Even once a person has realized that they’re some kind of trans, our genders and experiences of gender are kaleidoscopic—even two binary trans men will have radically different experiences of what it means to be a man. Hell, I got into a chat with two other trans women and an agender femme last week about what our genders felt like to each of us at our core. One of the binary women had an answer very, very similar to the agender femme, none of the binary women had a similar answer to each other, and we were all super excited to hear each other’s experience of gender because we ended up admiring them all, even though they were so different from our own.

Only they can know what their gender is. Only them, in the whole world.

Your job isn’t to identify their gender. It’s to help them give voice to those feelings.

Rule 9: Never pressure them about their identity

Remember what it felt like when you were questioning your gender, or when the truth you’d held in for so long was finally coming to a peak. Remember how terrifying, how out-of-control you felt in that moment. How crushing everything was.

Be safe. Be gentle. Let them come and go as they please, and never, ever pressure them to make a decision on who they are. Let them reach out to you, not the other way around. Sometimes, a person will need an hour or two of intense questions, and then they’re good. Sometimes, they’ll ping you off-and-on for months before they’re ready. Let them; there’s no pace too fast or too slow if it feels right to them.

Sometimes you need to give a person a firm nudge toward therapy, or getting support for an abusive relationship that they’re stuck in, and that’s perfectly fine. Always remember, though, their identity is sacrosanct.

Rule 10: Memorize this phrase, and fight to mean it when you say it

This is going to be the hardest one for a lot of people. You ready? Every time you start working with someone, you need to tell them this, and mean it:

I never take offense at anything asked in good faith.

Think back to when you were questioning your gender, or when you fought to keep yourself closeted. Remember all of the misconceptions you had about what it meant to be trans. Remember all of the harsh, cruel things you told yourself about being trans. About who you are. Remember the shame you felt.

And then remember all of the other things you worked your way through before you even got to that point.

If there’s one thing I’ve learned from talking to questioning people, it’s that pretty much every single aspect of being trans is widely misunderstood, and that means that you’re going to have to face those misunderstandings one after another in gender questioning people, over and over, because those misunderstandings are what are keeping them from realizing they’re trans.

They’re going to ask about fetish and kink. They’re going to ask about bottom surgery, including your bottom status. They’re going to ask about suicide rates. They’re going to ask whether they need to be straight. They’re going to ask whether they need to give up aspects of their current gender expression that they enjoy. They’re going to ask about autogynephilia. They’re going to ask whether it’s just trauma. They’re going to ask whether it’s because they were raped, sexually assaulted, abused as a child, or because they’re gay or bi or pan or asexual. They’re going to ask if they’re a pervert because they like their genitals the way they are. They’re going to ask if their sexual orientation will change. They’re going to ask whether it’s trans OCD. They’re going to ask whether their partner will leave them. They’re going to ask whether they’ll lose their job.

And that list? That’s just the really common stuff.

Know your boundaries. Know what answers you’re comfortable giving about yourself, what answers you’re not able to answer from your own experience, and what you want to keep private. Find resources to give them that’ll answer the questions that you’re not okay with answering from your own experience.

And whatever you do, no matter how indelicately they ask, don’t snap at them. Sure, tell them afterward—gently!—if they asked in a way they shouldn’t in the future.

But be gentle. They’re not trying to be shitty. They just don’t know what they don’t know, and many, many, many of them don’t even know enough about trans people to know that some things are rude. Remember: Katie Couric, one of the best journalists of her entire generation and with a whole team to help her get ready for the interview, once asked both Laverne Cox and Carmen Carrera, with her whole-ass outdoor voice, whether or not they’d had bottom surgery, on national television. And she thought that that was an okay thing to ask someone.

Not once. Not to a single trans person. But twice on a single program, to two separate trans women.

Questioning people don’t know what they don’t know, so they don’t know how to even ask their questions yet. Be patient. They’ll get there.

What comes after

If you’ve been paying attention so far, you’ve probably noticed something, so I’m going to say it outright: most people who ask a trans person for help with their gender isn’t really an egg anymore. They’ve hatched. They’re just afraid of the consequences, and needing emotional support as they come to terms with a world turned on its head.

But the thing is, as much as you need to work to meet them where they are, you aren’t where they are. If you were, they wouldn’t be asking you for help.

I mentioned earlier that in all the time I’ve been helping people, only about seven of the hundreds and hundreds I’ve helped have become friends. That’s because, as the people who you mentor come into their own selves, they’ll find that they don’t need you anymore, as they connect with other trans people near them who they can really connect with on a more real level.

They’ll drift away, contacts between you becoming rarer and rarer.

And that’s a good thing.

When you’re mentoring a hatchling, there’s a huge power dynamic at play. You’re out and proud, and yet you may be the only person in the whole world who knows the secret truth of those you’re helping. You hold their fate in the palm of your hands. For most people, as they grow in confidence, the specter of that power differential will start feeling a bit weird, and they’ll want to find other people, who are nearer to where they are in transition, and who they can have more equal, and therefore healthy, relationships with. A few you’ll meet will be ready and able to shed that unequal start, and you’ll be able to connect more deeply as people over time, but most will fade.

It’s one of the hard parts about being a teacher: you get to know someone, dust them off, give them a hand up, pat them on the back, and watch them walk out of your life forever just as you got to really know them. Bittersweet, because you’re proud that they don’t need you anymore, but then again it’s sad for the exact same reason.

A lot of people stop, or pull back from, doing this work eventually. It’s tiring, emotionally-intense work, and no matter how vital it is, there’s only so much any one person can give. I think it’s one of the big reasons why our trans elders tend to fade out of trans community so often—they just want to rest, and get on with their lives. If and when you find yourself needing a break? Or to just stop forever?

That’s okay.

There’ll be others ready to take their turn as a big sibling.

But for those of you who stick it out long term, there’s a little something beautiful that starts to happen after a few years.

Out of the blue, you’ll start getting little messages from the people you helped long ago. These aren’t exact quotes from people, because it wouldn’t be right for me to share those things, said to me in confidence… but I’ve received messages of each of these types, and many more, over the years.

• “My bottom surgery date is next week, and I thought of you. Thank you so much for helping me back then!”

• “My kid just came out to me! They’re nonbinary! I’m so excited!”

• “My spouse and I just had a vow renewal, and it was magical.”

• “I was putting together a timeline and I remembered that shot I sent to you when I was questioning. I thought you’d get a kick out of seeing how I look now.”

These little notes, snapshots into new lives that you helped give people the confidence to launch into—they’re my very favorite part of doing this work. Shining little crystalline gems of a joyful life that appear out of the blue, and they’re always the highlight of my day. I get notes like them from my former students too, from time to time.

They’re always rare, but if you do this work with enough people and for enough time, they always come, like the rain to the desert.