My 40th high school reunion

I’m dictating this post as I bike home after my 40th high school reunion.

I went to a snooty private high school. There were about a hundred people [A] in my graduating class. I was friendly, or maybe even friends, with fifteen or twenty of the 100 [B]. But my friends and I were very much outsiders. It’s telling that of the circle of people with whom I was friendly, exactly four were at this reunion, other than me. Two of them, I was no longer friends with by the third year of high school, as we’d realized we genuinely didn’t like one another(s). The remaining two? Two of the most distant among those with whom I was friends.

I tried to organize something of an alternative get-together for a small number of us, those whom I imagined unlikely to be at tonight’s event. But I failed. I didn’t try very hard, and I didn’t get very far. I’m in touch with literally zero of my high school classmates.

A fact about me: I have dozens of friends from my high school and college years, and before – my closest circle of friends dates back to the years from seven to thirteen years old, friends from religious school in the neighborhood in which my mother lived for four of those years, where I spent weekends (and was, therefore, something of an outsider, as they all went to school together during the week). That close circle overlaps a bit with a close circle of college friends, in weird ways. (One of my college friends is the cousin of my closest childhood friend; two of the college friends went to high school with that same childhood friend.) All of which is to say, the fact I’m in touch with zero of my high school classmates is a kind of “revealed preference,” as the economists might say, revealing my preference to have nothing to do with (or, said more gently, my complete sense of alienation from) my high school.

At our thirtieth reunion, a group of five or seven of us retreated to the home of one of us, and we said something to the effect of, “Phew! We’re out of there. Next time, let’s skip the reunion and hang out, just us girls.” It was that which I tried halfheartedly to make happen with my “alternative get-together.” My attempts fell flat, though, and I learned later, they fell flat largely because most of the people on that list a) didn’t come to the reunion – exactly one did – and b) there was a second e-mail chain going around some much larger subset of the class that was the locus of planning and discussion. That chain? It was started and “managed” by our class’s most visible booster, a big donor to and fan of the school. Needless to say: I wasn’t on that e-mail list.

So instead of the alternative event, there I was with probably thirty-five or forty[C] people with whom I had had either no high school relationship or an attenuated one. One woman there I dated briefly my senior year. I like her, and we have some friends in common in adulthood. It was nice to see her. But our high school dalliance was brief and not deep – we liked each other, but there wasn’t a lot of substance to our relationship or interactions, then or now.

I was pleasantly surprised to have connected conversations with a couple of people either with whom I never had a connected conversation (one approached me: “N, we never even spoke when we were in high school, but you seemed like a cool guy. Who are you?” He and I chatted for several lovely minutes about real things – his mom’s dementia; my mother-in-law’s dementia.).

I had a lovely conversation with a woman with whom I wasn’t particularly friendly in high school, but with whom I had an eighteen-month or so protracted flirtation either after college. She and I never hooked up. We never dated. But we came mighty close. We had good chemistry then, though (I’m not sure why we never dated), and we had good chemistry tonight. Then and now, though, part of what both drew me to her and pushed me away was drama. She’s an actor. She was one then. She is one now. And drama is a big part of what she has to offer, for better and for worse. Drama is a big part of what draws me to her, and what pushes me away.

Two of the women, petite Jewesses, activated some hormonal fire in my loins. I had never been particularly drawn to either of them in high school, maybe just because they were so far out of my league. They’re not out of my league now. They’re both firmly in it. And I had a nice, warm interaction with one of them, and a weirdly physical moment with the other, who touched my arm so tenderly it was hard to imagine that we were in a seven-person homeroom together for four years, and I don’t think we ever spoke.

Another woman, a lesbian, with whom I didn’t have but one or two conversations in the four years of high school, but who was best friends with the aforementioned woman I dated my senior year, it turns out, have a lot in common in our current moment. Professionally, intellectually, socially.

I suspect that there will be three or four coffee dates that come of the evening. And that last one, the one who lives and works in y world, she will certainly be the first.

One of my biggest takeaways was that this is a crowd that looks different than my crowd. Exactly one of the women – the one with whom I had the post-collegiate flirtation – had visible gray hair. I will say, she looked fucking hot. Almost every other woman sported hair dye, and most of them, lip filler and taut cheeks of a sort I honestly don’t encounter very much in my life.

One, a woman with whom I never spoke in high school and barely know, or knew, is spectacularly beautiful and incredibly poised and socially adept, even while she somehow simultaneously manages to be both likable and transparently inauthentic. I spent the first hour and a half trying desperately to figure out who she reminded me of with her preternatural beauty and poise. It took me a while but finally it clicked. Isabella, with whom I had a tryst early on in my descent into commercial sex. Or maybe not so early now that I think of it – in 2002, 2003, 2004. This reunion woman, whom I will call Jane, looked astonishingly like Isabella. And not just astonishingly like Isabella, but astonishingly like Isabella in 2002, 2003, and 2004! A remarkable achievement for a woman who must be fifty-seven or fifty-eight. Isabella and I were the same age then (and now, presumably).

The men in this crowd? I have to say, we looked pretty damn schlumpy. More than a few were fat. Some of those who weren’t fat didn’t look like they’d bothered to dress for the event. Not that I was in a suit, but I looked good. I was an outlier: I’m not, usually, vain, but I was one of two or three guys in the room I would describe as even plausibly “hot.”

And the women: they sported a fair amount of hair dye, a fair amount of lip filler, and a fair amount of surgery. The few I found attractive were the least representative of these dynamics. The two sexy, petite Jewesses: I don’t know if they dyed their hair, but if they did, it was tasteful, and didn’t fully hide the gray. They certainly did not have lip filler or taut cheeks. A couple of the women were painful to look at.

Several of the others actually were painful to look at. One in particular was gaunt. My post-collegiate crush said of her to me, “I can’t bear to look at her! She’s so anorexic!”

Another, her skin was so taut it made me wince.

Of all the women, only two had more than five or six extra pounds. (“GLP-1s!” exclaimed T, when I told her about it.)

I don’t know what to make of this all. My circles are very attractive. Most of the people in it, in them, look good, are fit. None has had surgery, to my knowledge. Most don’t dye their hair. This was just a different world I was in.

The sad punctuation mark at the end of the evening: In high school, I was an outsider. Not an exile. I wasn’t so much excluded as simply not part of it.[D] I didn’t belong. My family wasn’t as wealthy. Our values weren’t the same as the values of most of the kids in this school. As I said, it’s telling that of the twenty or so percent of the population with which I was friendly, only two were there. The whole crowd gathered at the tail end of the evening to migrate to a restaurant owned by one of my classmates. The party was continuing. I had been left off the email thread planning that party. Not for any malicious reason, but simply because no one on the thread had my email address. (Two or three of the people did, actually, but didn’t notice I’d been left off the thread.)

As the crowd was migrating to this restaurant, I was torn. The truth is, there just weren’t that many people there with whom I wanted to chat – none of whom I knew in advance I would enjoy chatting with. I might well have been surprised by another conversation or two as the evening passed, with one or another of them.

But honestly, I don’t think so.

I think I had all the conversations I needed to.

At the same time, there were three or four I would happily have continued talking with. And one, a guy I was vaguely friendly with in high school with whom I didn’t even speak, to whom I didn’t even say hi. Because reasons, I have a hunch I wouldn’t really like him so much today. But still.

So as the crowd migrated, I pondered. What should I do? Should I continue the evening and go to the restaurant? Or should I get on a bike and ride seven or eight miles home?

I did the latter, and as I rode, I dictated this.

I’m torn. I’m not sure I made the right decision. I might have had another good conversation or two or three had I stuck around. But I know that the ethos of the event was not going to be one for me. I spent so much of the four years of high school feeling profoundly alienated. I have a hunch that that alienation, which was present throughout tonight’s event, would have mounted had I gone to the restaurant. I can’t say I’m confident I made the right decision.

But as I dictate this five or six minutes from my wife and my home and my scotch, I have no regrets.

Postcript:

I write this at 4 am. I woke up, ruminating, and feeling – just – sad. Sad about aging, about mortality. Sad about my sense of alienation and exclusion. And just sad. In my restless, sleepless pre-dawn thoughts, I found, on the school’s web site, a list of alums, sorted by year. And, being me, I ported it into a spreadsheet, and did a little math.

[A] There were 106 of us.

[B] I counted 25 with whom I was, at one point or another over the course of the four years, friends. And another 26 toward whom, if I had any feelings, those feelings were vaguely warm. Almost half the class. And/but. Fifty-five people, in a class of one hundred six, with whom I barely ever spoke, with whom I had no relationship. It’s hard for me, as an adult, to imagine being in a class of a hundred, and not speaking (or being spoken to) by more than half of them. I want to be clear: I’m not saying people were mean or anything; they just were part of a world that I wasn’t a part of.