For Doug

(1987-2025)

Friends come and go, especially as life circumstances change. Classmates scatter around the world, ideological gulfs grow, and more things compete for our time. But it is easy to think that this is not truly “the end” — that these connections, even if not as critical to us as they once were, will come full circle, that some sort of cosmic string still intertwines you for at least one more intersection of paths.

Recently, one of my closest friends from middle and high school, Doug, died at 37. I had not talked to him in well over a decade. When we were classmates together, it felt as if we were unlikely ideological comrades — though me the overachiever and he the unrepentant slacker, we were both people who openly and vocally rejected the highly conservative and Christian culture of our Tennessee prep school.

Many of the other “gifted kids” wrote him off as not worth the time, but the more I got to know Doug, the more I understood that he had a lot to teach me. My family, especially my father, piled all sorts of expectations on me about the person I had to be. Though I have a genuine deep intellectual curiosity, I spent much of my younger years living in an inauthentic way designed to conform to the expectations of society.

Obviously, being a closeted trans kid will do that, but it went far deeper than that. Many who knew me from back then are deeply surprised to learn that I now have multiple tattoos and a tongue piercing, that I speak positively of my extensive experiences with cannabis and psychedelics, that various other ways I live now clash with the extremely straight-edged image I projected as a teenager.

While these are the product of many, many years of soul-searching and effort towards self-acceptance, I can’t help but wonder how repressed I would be had Doug not prodded me to not be inauthentic for the sake of other people. Ironically, Doug would go through what, at least to an outside observer, felt like an inverse process: joining the military and seemingly becoming more conservative.

Given we grew apart after high school, it was easy to imagine the worst from afar, that the man I had once considered one of my closest friends would be disgusted with what I had become. But, now that Doug is gone, I can’t help but regret not at least trying to reach out to him anyway. At worst, it would’ve confirmed my worst suspicions. But there’s a good chance that I was just letting myself be worried for no reason.

This is not the first time that I let a connection wither because I figured I was doing them a favor only to regret it later. My goal now is to make it the last. As we live increasingly digital, atomized lives, it is even more important that we learn how to bridge the chasms, real and imagined, between us and those that matter to us.

Yes, it’s important to find yourself and be yourself, no matter what others think. But if someone matters to you, it is still critical to understand what they think and, if there are conflicts, to try to find a way past them. Maybe it won’t work, but at least you won’t be left asking, “What if?”