A Hard Talk About a Delicate Matter

The Brother to Brother peer mentorship program was something I didn't seek out so much as fall into. The wing that I live in became the designated mentor wing, and the staff and prisoners spearheading the project recommended that I stick around to take part. At least I didn't have to move out, the way that a lot of other people were made to do.

Compared to mentors who don't have twelve-hour-a-day jobs, my involvement in the program is minimal. I don't teach classes, I don't write curriculum, and I don't go around shaking every mentee's hand in gleeful welcome to the program. In fact, there have been a couple of occasions when mentees—people with no previous prison experience—were surprised to learn that I'm a mentor at all. I don't make a big thing of it. My approach is less performative than conversational. I prefer one-on-ones.

A few weeks ago, a transgender person moved into the wing. They're on the autism spectrum, small of stature, somewhat naïve, and utterly lacking the street smarts that help keep people safe in prison. This being their first imprisonment, they were offered an opportunity to skip the nightmare of general population by going through a six-month period as a mentee.

"You guys saved his life," one of my acquaintances said after seeing me talk with them. "Like, for real."

He was joking, but he might also be right. As for his misgendering of the person, that can be forgiven because they generally present as male and haven't yet fully come out as trans. Only a few of us have been told, and we've been asked not to say anything.

Partly because of their enthusiasm for model trains, Dungeons & Dragons–playing nerddom; partly because of their neurodivergence; and partly because of their intent to get involved in every positive activity possible, I've developed a connection with the new mentee. We talk about model trains. We discuss prison nonsense. We share experiences from our respective lives as weirdos.

One day last week, I became concerned. They told me that a lawyer was handling their name change and that, once that legal procedure was finalized, they wanted a reintroduction to everyone—a celebration of officially beginning their life as a woman. Decades of experience have taught me that this would likely become a fraught circumstance. I couldn't hold my peace.

"I'm all for living as what you feel is your true self," I said, "but as hard as that can be in the 'real' world, it's going to be even harder in prison."

"But I like women," they said, matter-of-factly.

Delicacy is for neurotypicals, I reminded myself and took my verbal filter offline. "That's irrelevant. A lot of people are here because they don't care about the desires or needs of others. If they want something, they're going to try and take it. It's no different here than outside of prison. If you live outwardly as a woman here, they're going to see you as exactly that, which to them means you belong with a man. They think of themselves as men. You understand how that could play out, right?"

"Yes," they said, "but I fight dirty. Eyes, throat, groin. I'm little and I'm not strong, so I'll do everything I can to protect myself."

Was this bravery or foolishness? The two are so often indistinguishable. I went on.

"That's fine for when you're already in a bad situation. What I'm talking about is conflict avoidance. I'm not going to tell you how to live your life, but I want you to be informed about the potential results of your decision."

I told them about my entry to prison as a young man, how my first hours, days, weeks, and even months were terrorized by would-be abusers and rapists. I told them about everything I had to do to avoid assaults and exploitations. I explained how, throughout it all, my adversaries never took my preferences into account, then I posed the big question.

"Are you so uncomfortable with presenting as male that you're willing to risk being physically, sexually, or psychologically traumatized by being honest about your gender? Don't tell me your answer. You only need to answer that question yourself. And please take your time deciding."

This issue will probably come up again. In all likelihood, I already know what their answer's going to be. I feel almost ridiculous for having asked it, but I see the matter as one of informed consent. Before I posed the issue, no one—not even the prison's mental health staff—had framed the situation quite like this. At least now they know what potentialities could lie ahead.

I've done my part for the moment. Only one thing right now is certain: I don't envy them.