This post was originally published on my Substack blog on August 24, 2023.
After the grand revelation that I had lived (mostly) in hiding for five decades, I experienced a great deal of confusion. One source of consternation was the fact that I didn’t think anyone would ever see me as feminine, including myself. I looked at myself in the mirror, and it was wrong.
I didn’t hate my appearance. After years of not liking my face, I had reached the point where I saw myself as reasonably good looking, and I had worked enough on my body that it was fit and functional. Actually, pretty darn good for a fifty-year-old man. I had even come to terms with my age, and the road ahead into the “second act.”
So, while my revelation shook me to my core, I was more ready to accept it than I would have been at any previous point in my life. But my face… My face was now doubly wrong. I had long wished for a more attractive face, none of this annoying facial hair, and more hair up top. Oh, how I’ve always longed to have hair!
I actually gave up on my hair at a young age. I tried letting it grow long, but it would only grow up. I had that kind of hair. I felt like a cotton ball in a washed-out medium brown. So one day in my late twenties I shaved it all off, and I kept shaving it for twenty-five-odd years.
Until last year. After my wife moved away, I was on my own for the first time in many years. Without the expectation to play a role, I began to discover myself. The girly tendencies I had felt forever started to resurface. I discovered an interest in cute shoes. And I basically inverted my shaving routine; I stopped shaving my head but started shaving everything else. I had always shaved my beard because I hated having facial hair. But the first time I got out of the bathtub with my legs smooth for the first time in four and a half decades (I was an early bloomer), I knew I would never stop shaving them again.
In letting my hair grow, I knew I would never achieve my achingly profound hair goals. After all, I was over fifty. I’m thin on top and there’s a point right at the crown of my head that’s just a tiny bit bald. Yes, I overuse adverbs when I’m in denial. It’s a bald spot. But I was happy with the result when my hair grew in. It felt right… but not half as right as when I first dyed it purple earlier this year. For the first time I looked not just okay, but fabulous!
My awakening was touched off by Doc Impossible’s blog, Stained Glass Woman. I’ve read that blog cover to cover, and I eagerly await her next entry. The article that’s relevant to my post today is Part Five: Panic. I wasn’t quite panicking at that point; I pushed that down until it bubbled up a couple of days later. In that post, Doc Impossible describes putting her face into an app that shows an example of how you would look as the “opposite” gender.
I had to know. I have Stable Diffusion installed on my computer. I installed it locally so I wouldn’t be sending a bunch of information into the cloud. The advantage of Stable Diffusion over a generic app (aside from the privacy issues) is that you can craft your prompt to control certain aspects of the result—and prevent the deformities that demonstrate that artificial “intelligence” deserves those quotation marks.
I dragged the selfie I had been using online into the “img2img” interface and wrote a prompt to turn it into a picture of a fifty-three-year-old woman with purple hair and glasses. When I saw the result, I wondered why whoever trained that model thought fifty-three was absolutely geriatric, so I reduced the age to fifty and specified that the result should have long hair.
I generated a series of images. I couldn’t stop staring at this one. I still can’t

Those are my eyes (for the most part; the algorithm hates different colors, so my blue eyes are a little bit of a gray-purple). That’s my mouth. My nose, my neck, even the cheekbones are all mine!
But I’m not gorgeous!
Could I be? Could a few years of HRT and some surgery on my heavy brows make me look even a little bit like this? And the big question: Is there any modicum of possibility that I could have that hair?
This picture is both me and not me. But the more I look at it, the more I see the me I’d love to be.