Leopard-Skin Pill-Box Hat
Well, I'm not dumb, but I can't understand
Why she walks like a woman and talks like a manThe Kinks, “Lola”
The transgender thing perplexes me. Like, what’s the point? When it really matters, anatomically, one is not what they represent despite all their efforts, so what’s the endgame? Nothing I have found has helped me gain any understanding of this curious compulsion. In the same way as the mystery of Jeffery Epstein - ranging from his existence and wealth to his demise - remains buried and begging for answers yet investigative reporters steadfastly refuse to dig despite abundant public interest, this is a case where the media coverage vastly exceeds the public’s appetite and yet still there is no basic explanation. On its face, the unspoken, but inherently true fact, is that it is odd for a man to insist upon being treated as a woman in all regards, and vice versa. In my mind, this is the biggest hurdle to gaining sympathy, and support, for the movement, other than by coercion. The message, from advocates, is always, “Shut up, that’s a woman!” But why? And, importantly, what explains the desire? Even with all the surgeries and hormones, what does this achieve? I would not consider, in a dating context, a surgically transitioned male-to-female to be a straight woman.
Outside dating, I would be happy to oblige the pretense, as a matter of courtesy, to the extent it this does not impinge upon the rights of others (the exceptions being in the cases of bathrooms and women’s sports). But one side is resolute that these battles must be won without ever stepping back to explain, calmly, just what it is all about. So, I am genuinely curious.
Trying to understand what would compel someone, I once wondered, seeing myself as a high-grade nonconformist, if I had the mettle to pull it off, so I resolved myself to dress as a woman, without explanation, for a whole week. Of all the characters (I think) I can pull off, it turns out, being a woman is not one. I had a panic attack just buying the clothes. But, I learned, I wear a woman’s size 4XL, and only stretchy fabrics fit. Thankfully, they carried many selection my size at Kmart.
I didn’t make it past the doormen before I broke and started telling them I was only doing this for a story, and I lasted only 2 brief outings in uniform, not a week. I almost fainted when my girlfriend started telling strangers that this was my first day coming out, barking at her angrily -
Cut it out, they will think this is real!
My highly affected instinct to project masculinity to cover-up my deep insecurities was overwhelming, almost painful, even though nobody was really buying it anyway. And why should I care if they did? They were all strangers - just people on a Manhattan sidewalk. But, oh boy, was I so fragile and easily angered, especially by the suggestion that this was real. So, it turns out, I do care - very much - and that I don’t have the balls to be a woman.
The two masculine intersex boxers competing as women in the Olympics, re-piqued my interest in this topic, as did meeting my intersex/transgender friend, Jet. NB, both boxers won gold at the Olympics, much to the expressed disproval, shown by protests, of the women competing in their weight classes.
Writing about Jet, as night turned to dawn, sitting in a donut shop, which is the only place in this little town that’s open 24 hours, a brawny woman in a stretchy, Y-back halter dress sidled up next to me on the bench seat and scooched into the table opposite. Her irrepressibly cute daughter, about aged 5, had decided it was time to have a donut in the middle of the night.
The woman was, clearly, transgender. Other times I had broached this topic, it didn’t go so well. A typical conversation went -
Me: Can I interview you?
Them: About what?
Me: Being transgender.
Them: Why do you assume I am transgender?
Me: Because it’s obvious.
Them: You need to be educated!
Me: That’s what this is about.
Them: Huff! [storming off]
Awkwardly, this point had already been stipulated in this case: the daughter was calling her mommy, “daddy.” Unusually nervous to ask, I introduced myself, suggesting an interview some time for the purpose of this article. I was pleasantly surprised to gain a not unpleasant reaction. Being neither overly keen nor violently allergic, she agreed. We traded numbers, then quietly parted.
I was still convinced she would slip the meeting until, a week later, I found myself at Panda Express, holding a donut in a bag like a fig leaf, while Amy (fake name) told me her story. She insisted this conversation be anonymous. I was flattered she assumed anybody reads this at all. It was also ironic, I thought, that someone doing something as generative of attention as transitioning would be shy about being the focus of such attention.
She is the first subject who I didn’t thoroughly cyber-stalk to generate background. She did me the favor of meeting me, and being open, and I appreciate that, so, out of respect, I didn’t spend a minute trying to engineer her personal life’s details. However, when I asked, innocently, where she went to college, I noted she was coy, answering “somewhere back East” to limit my field of identifying data. I was somewhat offended she thought I would look, and a little more upset that she thought I couldn’t figure things out. Although she didn’t give me much to work with, I have found a lot more with a lot less. But, again, I didn’t look.
Pecking at her orange chicken, annoyed in a way, like a dude who knows it would be unladylike to chow-down but who desperately wants to, she gave me raw, thoughtful, funny and articulate answers, always framing things in ways that were relatable and friendly. I was impressed by her candidness, sense of humor, cheerful attitude and intelligence. I probably shouldn’t say this, but, the quiet thought in most of our minds is that anyone who feels the need to do this is probably a little bit off, but, other than for wearing women’s clothes and appearing obviously as a man, she was remarkably “normal” and self-aware.
She grew up in my town as a boy. She transitioned about one year ago. She is married, for now, to a woman, but in the latter stages of divorce. She works in New York City at a Fortune 500 company doing something in software development. When she told her employer of her plan to transition, the very next day she noticed the bathroom door nearest her desk had been recategorized to “All Gender.” She speculates, I think correctly, this must have been at the behest of the CEO, otherwise it would have taken weeks to harmonize Human Resources, building maintenance, decorators and diversity advocates within a big corporation. When she ripped her skirt one day on the way to work, the other women pitched in to help her stitch it up, and she received this as a small, but significant, signal of acceptance. In many ways, I agree, the more subtle the gesture, the more normalizing its message. It is better to be tacitly accepted than to have headquarters put up yellow tape saying “lookout everybody, a transgender is here.”
I thought she would find my transgender experiment funny, so I told her about it. When I did, rather than laugh, she explained, this was how she felt everyday dressed as a man. So intense was her innate desire to be a woman that she wore female clothes under her male ones before she transitioned. She explained her compulsion wasn’t about kink or sexual fetish, but that she expected - or hoped - to see a feminine form in the mirror every time she looked, only to be disappointed. That she wanted to have women’s breasts. That she felt relief - freedom - to finally take the plunge.
I asked if her friends missed the guy who she used to be and she admitted she hadn’t really thought about it but that no one was surprised by her doing it, and that everyone had embraced her new identity. She is just a more unrepressed, contented female version of her old self.
Usually quick to answer with smart responses, she paused for a long second when I asked her if she minded telling her dead name. Then she said -
Wow, I hadn’t expected this reaction. For that to be so difficult to say. I, um - wow - that is something I hadn’t expected to be so hard to do.
Then she confessed that when her family get angry with her, for example her parents, they are more likely to slip and call her by her old male name. I asked her if she thought this was them reverting to an entrenched association out of stress or if it was meant to be spiteful because they were angry. Without hesitation she said it was the former because her parents enthusiastically embraced her transition. When I asked if her soon-to-be-ex-wife was angry about it, she said she believed she was, at some level.
“Passing” is the inside baseball term for pulling it off - i.e. for a trans-person being believed by the general public. She told me it is easier for trans-men to “pass” because they can gain musculature and facial hair with testosterone but trans-women cannot eliminate facial stubble, a masculine jawline, and man hands. But, although, trans-men have an easier time “passing,” then, she told me, they just are stuck being short men - the Napoleonic complex and all that. How bitchy, accurate, and funny - all at the same time - I thought.
Some trans-women, she said, go past the point of diminishing returns. It’s not worth 5 hours more make-up to look 1% more female, especially if one is not going to pass anyway. I thought it was interesting that within the community there is a notion of passing. Passing as what? A real man or woman? That implies an acknowledgment of what is vehemently denied — i.e. that biology more determines one’s gender than appearance.
I was reminded of "Mr. Garrison's New Vagina," South Park’s ninth season premiere, when I asked her if she liked men or women. In that episode, Mr. Garrison, having transitioned to Janet Garrison, visits a lesbian bar.
Amy explained to me that she has always been attracted to women, and that that hasn’t changed. Then, she giggled, playfully rolling her eyes, and said -
I guess that makes me a lesbian.
I was thoroughly impressed by her bravery, intelligence, and most of all her willingness to embrace the humor of the situation. She was refreshingly open and candid, without ever being angry. When I asked why so many trans people have gotten upset when I asked to interview them, she gave me the perfect answer:
Well, I guess, it would be like going up to someone and asking, ‘Hey, can I ask you some questions about your toupee?’
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