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.

The post My 40th high school reunion appeared first on My Dissolute Life.

An example from yesterday. It dawned on me that what I feel in the face of all the various women with whom I no longer have relationships is shame, a deeply felt shameful sense that somehow the fact of our no longer having a relationship must mean that I am on some profound, deep level, bad, undeserving, unworthy, that the end of the relationship necessarily indicates my badness. Is evidence of it, is the function of it, is conclusive proof of it.

I’ve written hundreds of times about how I use women to revisit the abandonment I experienced by my mother, about how when poison stood me up in August of 2009, I relived my mother’s abandonment of me in 1973. And while on some level I think I knew what I’m saying here, I also didn’t know it. I didn’t get that the feeling I was reliving was not just a cold sense of fear and loss, but also of shame, of responsibility. I think that latter part had previously been lost on me, at least consciously, such that when I had this epiphany yesterday, it felt genuinely like news, even though if I look back over this blog, over all the entries I’ve written about similar such feelings and experiences, it’s clear that this is not really news to me. And yet, somehow, it is.

It is, and it’s not.

That is how epiphanies work for me.

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I’ve never seen Yesenia look other than I’ve just described – though I’ve seen her dozens of times in contexts in which you might expect to find her in sweats or shorts or jeans.

I have the sense that other women are infuriated by the ease she projects, even as she inhabits an elegant and glamorous self-presentation.

God knows if I were a woman, I would resent her. I would envy her.

As a straight man though, I admire and appreciate the effort she puts in and the invisibility of that effort, except in her outfits.

I have written before that I believe, almost as a matter of faith, that people should only wear clothes that make them feel hot. I believe this of men and women. I believe this of outerwear and underwear.

Putting on faded, ratty, torn, worn, stained clothes can’t help but make one feel all of those things about oneself.

When I look at Yesenia – and I’ve only ever seen her fully clothed – I have the distinct sense that she subscribes to this philosophy, that it’s important to her that everything that touches her flesh make her feel beautiful and sexy. Certainly everything I’ve ever seen on her has accomplished that.

And so, I like to imagine what lies beneath what I see.

In my fantasies, Yesenia has an elaborate collection of expensive and diverse lingerie. Corsets and basques. Panties and bras. Bodysuits, bodystockings. Pantyhose, tights, stockings and garters. Silky cotton. Lace. My instinct is that the colors skew dark: black, brown, maroon, purple, crimson. But I’m open to being wrong, to the possibility that she’s got an entire collection of pastels, of whites.

Anything seems possible to me, except for one. She does not wear boring, old, worn lingerie.

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It always has.

The first death I remember was my mother‘s father who died at 55, when I was three-and-a-half, after a six-week illness – cancer, discovered late.

Five years later my dad‘s father died at 60, after an even shorter illness.

Four years after that, my mother’s mother died, at 62. I was twelve. She had been sick with cancer off and on for several years. So her death was a shadow over fourth, fifth, sixth, and seventh grades.

In the years between twelve and nineteen several of my grandparents’ siblings with whom I was close died. One after cancer, one after leukemia, one of Alzheimer’s.

And then, of course, at age nineteen my mother died.

That’s a lot of death for a young person, and it certainly shaped my experience of life. My child, who is now twenty-one has been to three funerals. At age one her mother’s grandmother died. Our child never knew her, and has no memory of that. At age six or seven we went to the funeral – or rather, the wake – of the father of a good friend of mine. And around that same time we went to the funeral of the husband of a childhood friend of mine, the first premature death our family faced. But it was not a close friend, not someone our child really knew or mourned.

So, now, at age twenty-one, the first real funeral hasn’t yet happened. But death is knocking at our familial door. My wife has step-siblings. Their father – the ex-husband of T’s stepmother – just died. Tomorrow we’ll be at his funeral. Our kid won’t be. This is someone she never met, she didn’t know.

But death nears.

We can smell it now.

Our kid has six living grandparents, five of whom are over the age of eighty-five, and a plethora of great aunts and uncles.

I have the sense it might be time to go suit shopping….

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I didn’t write, though, about some of the symptoms of this depression, apart from my tears and my mournful aspect.

The first, the most prevalent, is when someone asks me how I’m doing, I don’t have an easy answer. “Fine,” “Good,” “Awesome,” “Really great!” – answers I’ve historically accessed quite easily – feel inauthentic and inaccessible in the current moment. But there’s not some other answer. “Shitty, thanks!” “Sad.” “Struggling.”

That feels, at least not often, like a response no one wants to get, I don’t want to give, as it opens up a conversation that most people asking how I’m doing didn’t really want to invite. So, that’s my most prominent symptom – a sort of confusion in the face of a very basic performance of social nicety.

Following a close second behind, though, is my essentially absent libido. I’ve written at times about my sense of deadness, about the ways that I use porn and women to enliven me, to wake me up. In the current moment, though, I’m barely even doing that. I just don’t have the energy or the appetite. I don’t crave physical intimacy. And the work associated with emotional intimacy feels like, well, like work.

So, in a sort of spirally, self-destructive way, I isolate a bit. A good friend invited me to dinner the other night at the last minute. Circumstances were such that I could perfectly well have gone. T was out of town. I didn’t have plans. I like my good friend. His family is lovely. An evening there would have been, no doubt, a good addition to my week. A good ending to my week.

And yet, without really thinking about it, I found myself first not responding to the invitation, and then, finally, sending my regrets.

The post Depression part 2: symptoms beyond sadness appeared first on My Dissolute Life.

While I’ve done more than my share of grieving and mourning, I’ve been dealt far less than my share of melancholy, of depression. I often feel fortunate to have access to as much sadness as I do, sadness about what my life has and has not held thus far. Sadness about the suffering of those I love and those who are further from me. Sadness about the transience, the impermanence of everything good (and everything bad).

I’ve written before that this sadness feels to me like a gift. At the same time though, and this may be evident if you’ve been reading, at the moment I am contending with a bit of depression of my own. It’s not crippling. It’s far less extreme than some depressions I’ve witnessed. But it is pronounced and undeniable. It creeps out, seeping, leaking, leaking under the doors of various rooms of my psyche. It infects how I think about the future. Whether it’s the future I ponder with the people I love, the future I ponder with colleagues or in work, the future I ponder with women whom I date or haven’t yet met but hope to.

It infects everything, coating it with an ooze of morose lethargy. As I said, it’s not that severe. I don’t struggle to get out of bed. I’m not anhedonic. I have lots of fun. It’s just that if I pause for a moment, if I stop and reflect, what bubbles to the surface is a slightly tearful, mournful sense of loss, of sadness.

The post Depression appeared first on My Dissolute Life.

It began with my dictating a voice memo as I biked home, which my “voice memo processor” – basically, an unnecessarily complicated Rube Goldberg situation – reduced to:

Summary

I want to build a whimsical Next.js app for rating french fries across attributes like length, girth, crispiness, potato flavor, and greasiness. It will feature 1,000 simulated NYC restaurants with fictional reviews, plus a user-submitted wiki section, maps, fry photos, and funny content.

Outline

1. Core Concept

• French fry search/rating app
• Attributes: length, girth, crispiness, potato flavor recognition, greasiness (scale 1–5)
• Additional metrics TBD

2. Two Sections

a. Simulated/Fictional

• 1,000 fictional restaurants
• Each with unique rating mix
• 2–5 opinionated reviews per restaurant

b. User-Submitted (wiki-style)

3. Geography

• Based in NYC
• Concentrated in Manhattan
• Additional entries in Brooklyn, Queens, Bronx
• Map integration

4. Content & Style

• Lots of french fry photography (McDonald’s to steak frites)
• Oil type and fry method info (single/double/triple fry)
• Funny, whimsical tone

5. Technical

• Next.js website (v1)
• Geographic/map features

6. Next Step

• Up to 20 clarifying questions before build begins

I then pasted that into Claude, which dutifully asked me 20 questions. My answers to those questions were:

1. What’s the difference? Why do I care?
2. I have no idea
3. AI-generated, but static/in advance
4. Mock only
5. Open/anonymous
6. Google maps
7. Secondary
8. Pre written and seeded
9. Christina’s Fry Guide
10. Michelin
11. Wiki only
12. Still open. Suggest others!
13. Yes!
14. I can find you images – I’ll find you several
15. Demo/portfolio
16. Mobile first
17. Seeding is fine
18. No
19. Filterable
20. Vercel

Based on that, it asked me two more questions, which I answered:

1. A character! I’ll find you an image.
2. The former

It then gave me a Zip file, which I downloaded to my local (Windows) machine. I didn’t entirely understand it, and/but uploaded about ten pictures of Fries, and an AI-generated simulacrum of my date. It updated the Zip file, which I couldn’t figure out how to use/what to do with. So I switched to Claude Code, where I took it the last few steps, to completion.

There was a little trouble-shooting around getting the photos working, but now, it’s done. And damn.

That was, literally, less than an hour of my time.

The post The ridiculousness of ai appeared first on My Dissolute Life.

Over time, the blog itself became something of a chick magnet. Veronique and Sophia were the two best examples of the blog’s working this way. They each stumbled on the blog in their internet meanderings and reached out to me, introducing themselves and launching torrid affairs.

There were other examples of that over the years, but in the last 5 or 7 years, that has really come to a stop, for reasons having to do with some combination of the changing dating world, the changing internet, my age, and who knows what else. It just doesn’t happen anymore that people stumble on the blog and say they want to suck my cock.

Add to which, 15 years ago when I was swiping right on those hundreds and hundreds of Tinder profiles, I was prepared to put in some work. I understood that if I wanted to meet women via the apps, I had to spend some time to make it happen. Nowadays, I just don’t have the interest. I don’t know if this is about my libido or about my maturity, but the thought of spending hours hyping myself on apps to women, a tiny proportion of whom might conceivably be interested in me, just doesn’t appeal. Add to which, the evolution of apps like Feeld, which caters to the poly crowd, just highlights how non-normative I am. There’s a whole universe of swinging 20, 30, and 40-somethings openly dating, engaged in some various permutations of kitchen table polyamory.

It seems like there are a lot fewer women in their 20s and 30s and 40s exploring their sexuality – my catnip – receptive to a companion and guide in his 40s or, God help me, late 50s. And maybe that’s the issue. Maybe there’s a real difference between late 50s and early 40s.

I mean, I know there is. But gosh, does it make me sad.

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Just over fifteen years ago, my then-girlfriend L suggested that I should write this. “You have an interesting sex life,” she said, “an interesting history, and you write good. People would be interested.”

I wasn’t sure about the “people would be interested” part, but I had the sense that there might be something for me in a somewhat exhibitionistic/navel-gazing retelling of various aspects of my story, past and present. Boy was I right, boy was she right, boy am I grateful. This blog has been pretty radically transformative for me, an essential transformative and liberating feature of my forties and fifties.

When I began, I was very focused on my audience, on my readers. ‘How many people came to the blog today?” “How many people commented?” “How many people read which posts?” All that was of manic fascination to me. And I worked assiduously to grow my readership, my reader engagement. I even tailored what I wrote, both to people’s interests and to maximize traffic. I used various analytic tools and engagement tools, and there were months when I spent as much time on the project of maximizing readership as I did on the project of writing.

Over the years, my relationship to all that shifted a bit. My narcissistic hunger for recognition and appreciation has ebbed and flowed over the years, but in general, it has receded substantially, to the point that today, my sense is I’m a little bit of a vox clamantis in deserto, a voice crying out into the wilderness, speaking my truth, or at least parts of it, without reference to the question of whether anyone is listening. And my sense is that for the most part, no one is. And honestly, that’s just fine.

Where the project began as an exhibitionistic and therapeutic, cathartic exposure of that about which I previously had felt tremendous shame, it’s morphed into something more of a memoir, a record, less and less as the years pass, of my sexual partners and activities, and more and more of the goings-on in my head as I march through my fifties.

Today, the end of my fifties is, if not in sight, just around the bend. My libido is considerably less urgent than it was fifteen years ago. My hunger for recognition, considerably less. My appetite for disclosure, even, considerably less.

I want to nod, though, in the direction of some of the things about which I have not written over the last fifteen years. When I began this blog, I was at the tail end of a career. A career that ended somewhat prematurely, in part because of realizations to which I came in the wake of my addictive relationship to sex, and in part because of involuntary changes in my ability to attend to much of what was required me in my previous career. For the first four years or so of this blog, I effectuated a major personal and professional transition. First, being a stay-at-home dad for two years, and then completing a second master’s degree in a completely unrelated field to anything I had pursued previously. And then, subsequent to that, depending on how you count, I spent either four or ten years, or both, pursuing this new career, becoming a professional in a new field in which today I’ve established myself as a somewhat respected and accomplished participant.

All that has happened without my really characterizing it here. But that’s kind of interesting, because it’s unusual for someone to reinvent themselves in their forties in the way that I did.

And that’s a whole other interesting story that I just haven’t told very much. Nonetheless, it’s true, lurking in the background. In addition to that, T and I have had a kid, obviously, all this time. A kid who was five or so, or six, when I started this, and who, today, is twenty-one. I’ve worked hard to protect T and our kid’s privacy. T, of course, has known about this blog all along, and our kid, though she hasn’t known of it directly, explicitly, certainly is aware of it in a variety of ways. (Close readers might notice that the pronoun by which I refer to our kid is not the same pronoun I’ve used in the past. And maybe in the coming days, I’ll write a bit about that. Both about the intellectual aspects of having a trans kid, and about some of the emotional elements of it. It’s a little hard to do in a way that feels respectful, but I might take a crack at it.)

Anyway, I’m writing this without really having a fundamental point beyond one of gratitude for the role this blog has played in my becoming the man in the late fifties I am, in traveling the journey that I began as a man in his early forties, when this blog began. I’m grateful for the role that the blog has played, and to the extent that you’ve been reading along, that you have played in my journey.

I couldn’t have done it, I wouldn’t have done it, without your help.

The post Happy 15th blogiversary to me appeared first on My Dissolute Life.

From the moment my child was born, I was kind of resolved not to deprive her of my output in the event of my death. This isn’t out of a grandiose sense that any of what I’ve written is particularly important, but out of a commitment not to repeat the trauma I experienced by losing so much of my mom, of her writing.

I don’t know that I actually would have read much or all of what she had written, but I certainly would have, from time to time, dipped into it, looking for answers to questions. I don’t imagine my child would particularly relish the opportunity to read the bulk of what I’ve written in this blog. It’s not the kind of stuff a kid wants to read by their dad. At the same time, my kid is increasingly not a kid. As she reaches adulthood, I could imagine she might begin to feel different about some or all of the content here. I know that when I was my kid’s age, I would have recoiled if I were to have read anything my mom had to say about sex. But that was then. So, I would have recoiled in my late teens and early twenties, but by the time I was in my thirties, never mind now, in my mid-late fifties, honestly, I think I could handle it. Anyway, I had that fantasy about creating some sort of a chatbot that could speak in my voice, and ideally with my voice, long after I passed from this mortal coil. The early days of LLMs had convinced me that that particular fantasy was not likely. Even the most sophisticated imitators of my voice do a shitty job, both at capturing my style and at anticipating what I might actually say in response to any given question. In recent days, though, I’ve embarked on a bit of a new experiment with respect to a chatbot. Not trying to imitate my voice, but trying to give access to what I’ve said in a useful way. This is a project of Claude Code, and I’ve been using a combination of tools provided by OpenAI and Anthropic to do it. It’s very much a work in progress, and I expect that it will continue to improve.

In my first iteration, I had it speak in my voice, or in the first person. That was a mistake, because the whole uncanny valley aspect of it rendered it absurd. It just so clearly wasn’t me, it so clearly was some sort of simulacrum, it was just spooky. So I’m getting rid of that, and instead trying to make it be nothing that it isn’t, and precisely what it is. Give it a whirl, and let me know your thoughts.

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