Posted on by Matt Thomas

The Days and Nights of My 50s I: 7/20/26, the Unwritten Libretto.

Author’s Note:

Five days ago, I made what may prove to be the most important professional decision of my life.

For months—years really—I had been thinking about giving up my teaching career and becoming a full-time writer. I have talked to many of my family and friends about this and taken several small steps in this direction. I recently published a novel, have written and published hundreds of essays, and written almost every day for eighteen years. I have hundreds of pages of dream records, journals and letters, some sent and some only in draft form. I am hard at work on the sequel to my first novel, and am currently working on five books with many more in the making.

Over this time I have also become very good at making excuses. School is too busy. Life is complicated. The timing isn’t quite right. Next month. Next term. Next year. One day. It was all true, and yet it barely matters. A few days ago, I finally admitted what had been staring me in the face for a long time: if I wanted to call myself a writer, I had to stop waiting for someone else to make that decision for me. Whether I eventually succeed or fail is almost beside the point. The decision itself changed something in me. I stopped thinking about the life I wished I had and started taking responsibility for the one I actually have.

Today wasn’t the happiest day of my life, nor the saddest. It wasn’t the day I got married, the day my son was born, the day I published my first book, or the day I realized my marriage was ending. Objectively speaking, it was an ordinary Monday in Osaka. I listened to music. I wandered the city. I shared dinner and my bed with a woman whose path happened to cross mine for a couple of hours before diverging forever. By tomorrow morning she would be somewhere else, and so would I. Yet somewhere between checking into a modest hotel, thinking about my future, and sitting alone quietly after she left, something finally clicked. My teaching career is rapidly coming to a close. The marriage that defined most of my adult life is over. The books I dream about haven’t been written yet. The cities I may someday call home are still only possibilities. The people who will matter most over the next twenty years are, at this moment, complete strangers.

For the first time since I was a young man, there is no obvious script. That realization is exhilarating. It is also terrifying. Most of all, it is deeply liberating.

So this seems as good a place as any to begin this series.

Epigraph:

Yesterday is history. Tomorrow is a mystery.

Anonymous

Anything could happen.

Bash and Pop

I: My General Situation As of Today

For the better part of thirty years, my life had possessed a remarkable amount of structure. I graduated from college. I moved to Japan. I found a teaching career almost by accident and stuck with it for a quarter of a century. I got married, and my wife and I bought a house together in Kyoto. We raised a wonderful son together who we both love more than words can say. We have paid bills, argued over groceries, worried about our dear dog Daisy, taken vacations when we could afford to, and slowly accumulated the ordinary rituals that eventually become a life. There were wonderful years and there were difficult ones, but there was almost always a next step waiting patiently in front of me. Whether I liked the script or not, there was a some kind of a script.

Then, almost imperceptibly at first, it disappeared.

My marriage ended not with a single dramatic explosion but with the gradual realization that two decent people could simply reach the end of the road together. My teaching career, once the defining feature of my adult identity, began to quietly recede into the background. Friends scattered across countries and continents. My parents grew older. I turned fifty-two without feeling especially old, but with the unmistakable sense that I had entered the second half of whatever story remained.

It is a peculiar thing to discover that freedom and uncertainty are twins. For years I imagined freedom as something uncomplicated. Finish work. Write books. Travel. Meet interesting people. Drink coffee in strange cities. Listen to music until two in the morning. Wake up whenever I pleased. Answer to no one.

There is truth in that fantasy. There is another truth as well.

Freedom also means that no one hands you tomorrow. No institution is waiting to promote you. No family obligation automatically determines your next decision. No invisible current carries you downstream. Every meaningful choice becomes your responsibility. Every success belongs to you. Every failure belongs to you too.

That realization can feel less like opening a door than standing on the edge of a cliff. You can step forward. Or you can spend the rest of your life admiring the view. Five days before the evening you’re about to read about, I decided I was done standing still.

I wasn’t retiring, not yet anyway. I wasn’t exactly reinventing myself. I wasn’t chasing some impossible dream. I was simply acknowledging something that had probably been true for twenty years. I am a writer. I feel like I was born to be one. Whether anyone else eventually agrees is, in many ways, beside the point. The work itself has become the destination. Everything else—the cities, the books, the women, the music, the bars, the victories, the humiliations, the friendships, the failures—is simply material for my work.

This series is an attempt to pay attention to the contours of my daily life, in whatever form the may take. And, perhaps for the first time in my life, to trust that the story doesn’t need an outline before it begins.

II: Osaka

Osaka has always felt different to me than Kyoto.

Kyoto is the city where I built my adult life. It is where I have worked, and lived for more than twenty years with my life and son. It is where the mortgage was paid and our dog was walked, where ordinary afternoons quietly accumulated slowly into decades. I know its rhythms inside and out. I know which coffee shops open early, which bridges are worth crossing at sunset, and where to stand beside the Kamogawa when I need to remember that almost everything eventually passes.

Osaka has always been to me something else entirely.

It has never asked me to be responsible. When I come here, I feel somehow lighter. Less like a teacher. Less like a husband. Less like the man who spent twenty-four years inside the same corporate institution. Osaka has always given me permission to become, if only for a day or two, a slightly different version of myself. Not a better man or a worse one. Just someone with fewer expectations resting on his shoulders.

Perhaps every city we visit has a role to play in our lives. Kyoto has been my home. Tokyo has often been a dream. Singapore has long been my favorite escape. Osaka, though, has become my intermission. A place where I can step off the stage for a little while before the next act begins. A place to just get away.

This Monday afternoon I checked into a small APA Hotel not far from Shinsaibashi Station, which I affectionally call Mr. Shin. Like most APA hotels, it is clean, efficient, and just a little too compact. The room isn’t exactly designed for lingering. It is designed for sleeping, showering, and moving on. My suitcase for neatly against one wall. The desk is barely large enough for my laptop and a cup of coffee. The large television in front of my bed I will barely use. It suits my current mood perfectly.

I took a taxi to the hotel from Shin-Osaka Station and arrived around 7:30 PM. I dropped my overnight bag on the floor, drew the curtains apart, and looked out over another slice of Osaka. Nothing spectacular. Just traffic, apartment buildings, and the quiet machinery of a city getting on with its day.

I remember thinking how strange it felt to have absolutely nowhere I needed to be. No lesson to prepare. No meeting to attend. No papers to grade. No one waiting for me at all.

That realization no longer frightened me the way it once might have. It felt… spacious. There are moments in life when freedom announces itself with fireworks. This wasn’t one of them. It arrived almost silently. Like an empty afternoon. Like a city that has never asked me to explain myself. My hotel room is simple. It is what I can afford.

Outside, Osaka continued exactly as it always had. Inside, almost without me realizing it, the next stage of my life had already begun.

III: Meeting Yuki

I should flash back briefly here to introduce my date for the evening. There are evenings that require months of planning. This was not one of them.

The plan, such as it was, consisted of very little. Conversation. Sex. Cigarettes. Dinner. That was enough. As I stepped out of the taxi, I saw her standing quietly on the street.

She was slightly built, dressed in a simple black skirt, and carried herself with the quiet confidence of someone accustomed to meeting complete strangers. There was no dramatic meeting, no cinematic slow motion, no instant thunderbolt. We smiled, introduced ourselves, and within a minute or two were walking side by side into the hotel through the warm Osaka evening as though we had agreed to meet as old friends rather than someone we had never laid eyes on before.

Her name was Yuki.

We went up to my room and made the sort of awkward conversation that strangers always make at first. Where are you from? Where do you live today? Had I been to Osaka often? Was I enjoying the summer?

Nothing remarkable. Which, in retrospect, was itself remarkable. There is something deeply comforting about ordinary conversation. For a little while, neither of us had to be anything more than two people just getting to know each other.

Eventually, because pretending otherwise would have been absurd, the reason we had met entered the conversation. She is thirty-six and works as an escort. I had hired her for the evening.

There is no point dressing those facts up in prettier language. They are neither the whole story nor something I feel any particular need to defend. They simply belong to it. Human lives are untidy. We make decisions for reasons that are sometimes noble, sometimes lonely, sometimes curious, and sometimes impossible even to explain to ourselves. This was one of mine.

I went into the bathroom to wash up, took my clothes off, and hung them neatly on the hangers on the wall. By the time I came out of the bathroom she was naked too. That was what we were there for. I put on one of my favorite bands Whiskeytown, lay back on the bed for a few minutes, listened hard, and let the sweet sweet sounds of Ryan Adams’ voice wash over me. I was, briefly, in heaven.

Then, inevitably, we began to kiss. She is a smoker and tasted like stale tobacco and faintly like green peas. I am a smoker too so I am sure I tasted the same. She unwrapped one of the condoms that I had bought earlier for occasions just like this and began to pleasure me with her mouth. While I do enjoy oral sex to some extent, it is far from my favorite sexual act and I have never been able to cum this way. Not for lack of trying, I simply find that the women who have performed the act on me can never sufficiently been able to get their teeth out of the way. It is not their fault at all, but it is just that simple.

Soon enough, I asked her to climb on top of me. My penis was already erect and she was slick as well, and I entered her cleanly and easily. After a little while, we flipped around and began to engage in the missionary position. I was on the urge of cumming when I pulled out, turned over on my back, and finished my self off with two hands. Nine times out of ten I finish this way if I finish at all. After all, I know my own equipment better than else, so to speak. Before we began to have sex I put on some porn. I chose very quickly as we were on the clock. I selected some perfectly nun priest porn, totally chalk. Of course we both barely watched it as our eyes were mostly closed. The moment I came I toweled off, shut off the porn, and immediately pressed play on the Whiskeytown video I had paused before sex.

Then a funny thing happened. During sex she had repeatedly asked me to turn down the porn and to shush in general. She said we were at a business hotel and that we were bothering the other guests. Although I love to be babied. I do not like to mothered at all. It is just not my thing, and I have written about this at some length here. I already knew that I would not book Yuki again, and this moment helped crystalize my decision. She is sweet and cool, and I am glad I met her for one night, however she is just not my jam. And also, nobody shushes my boy.

Anyway, she asked me to turn my music down. I just laughed and cranked it. Then she laughed too and the mood lifted and passed. Neither of us was yet in the mood for a shower, mostly because we were on the clock and by this point only had about 40 minutes left in our appointment. I did not feel like a round two, so I suggested we head down to the street to smoke for a smoke and then get a little dinner. Although we had less than an hour left and the hotel restaurant was a little busy, she agreed to have dinner with me.

We finished our cigarette and entered the first floor hotel restaurant. We sat down and briefly consulted the menu. The restaurant specializes in pasta, so I ordered tomato pasta with eggplant and she ordered the zucchini linguine. The food took a while to arrive, so halfway through the meal she asked for a doggie bag. I quickly finished my meal and we went upstairs so she could pack her bag.

The evening had never pretended to be anything it wasn’t. Neither of us confused it with romance. Neither of us imagined it was the beginning of some extraordinary love story. It was simply two lives crossing for a few hours before continuing in different directions. There is something quietly beautiful about that too.

Outside, Osaka was still very much alive. Trains rattled somewhere in the distance. Traffic rolled steadily beneath the hotel windows. Thousands of strangers were beginning nights that had nothing to do with ours. Ours, quietly and without complaint, was coming to an end.

I told her I was going to wash up for a minute. She said through the door that she had to leave. I said goodbye babes and she replied in the same fashion. When I came back out, she was already gone.

And I didn’t even kiss her goodbye.

IV: Coda

For most of my adult life, my future had always arrived with an outline. There was always another semester to teach. Another report to write. Another mortgage payment to make. Another family holiday to plan. Another school year waiting just over the horizon. Even when life became difficult, I almost always had a sense of what would come next. The details may change, but the broad shape of the story had already been sketched.

And now it hadn’t.

As I write this the marriage that defined nearly half my life has come to an end. My teaching career, after almost thirty years, is slowly coming to an end. My son is a grown man, trying his best making his own way in the world and earning his own money. My wife and I are immensely proud of him as well we should be. Our house of 19 years will soon belong to someone else. My life is rapidly becoming quite different and everything that had once seemed permanent has become part of the past.

This all may sound just a bit sad. Some of it may be, sure. It also happens to be exhilarating. Tomorrow I might wake up in Kyoto. Next month I might find myself in Singapore. A year from now I may be living in Osaka. Anything could happen.

Perhaps I’ll write ten more books. Perhaps no one will read them. Perhaps I’ll fall in love again. Perhaps I won’t. There will be close friends I haven’t made yet. There are cities I have not yet wandered. There are songs I haven’t fallen in love with, thank god.

There are mistakes waiting patiently for me. There are joys I cannot yet possibly imagine. For the first time since I was in my early twenties, the next chapter of my life has not yet been written.

As I stood there in that little Osaka hotel room, listening to Whiskeytown waft through the room, I finally understood what life had trying to tell me for days.

My life hadn’t fallen apart. It had, in fact, opened up. And somewhere beyond everything I thought I knew, waiting patiently for me, was the unfinished libretto.

Dedication:

For Yuki. Thanks for a lovely evening. I’ll never see you again, babe. Go with God.

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On The Dubious Anna Delvey

Note: This essay reflects on the curious cultural figure of Anna Delvey, whose rise and fall in the New York art and social scene became one of the stranger morality plays of the late 2010s. Delvey—born Anna Sorokin in Russia—gained notoriety for presenting herself as a wealthy European heiress while attempting to secure loans and social capital for an ambitious but largely imaginary cultural venture known as the Anna Delvey Foundation.

The events described here draw on widely reported elements of the case: Delvey’s years moving through luxury hotels in Manhattan, her efforts to obtain financing for a private art and social club, the unraveling of her financial claims, and the now-famous trip to Dubai in which a friend—later a magazine writer documenting the experience—was left responsible for an enormous hotel bill after promised funds failed to appear.

The piece does not attempt investigative reporting. Instead, it approaches the story in a spirit of cultural anthropology. Cities like New York have always attracted individuals engaged in various forms of self-invention. The line between ambition, performance, exaggeration, and outright fraud can sometimes appear only after events have run their course. Delvey’s story is compelling partly because it dramatizes this thin boundary in unusually vivid form.

If the tone here sometimes drifts toward sympathy rather than condemnation, that is intentional. Many urban cultural scenes—especially art worlds—operate on the energy of strivers who are, in one way or another, attempting to become something slightly larger than their present circumstances allow. Most of them eventually succeed or quietly disappear. A very small number, like Delvey, collapse in public.

Their stories reveal something not only about themselves, but about the environments that briefly believed in them.

Epigraph

“For all the crazy people who can never get it right.”
— Drugstore

I. The Entrance

There is a certain kind of person who arrives in a city not merely to live there but to declare themselves into existence. Cities like New York attract them the way bright lights attract moths. They arrive with luggage, ideas, clothes that signal belonging, and an almost reckless confidence that the future will eventually arrange itself around their intentions.

Anna Delvey was one of these people.

When she appeared in the New York art scene, she seemed to possess the basic ingredients required for entry into that peculiar ecosystem: style, confidence, and an air of European mystery. She wore expensive-looking dresses and shoes. She wore aa lot of make up and had her hair done at expensive salons. She seemed for a while to ooze money. She spoke casually about ambitious cultural projects. She moved through hotels and restaurants as if she had always belonged to that world. In New York, that is often enough.

The city runs on confidence performances. Every ambitious young person who arrives there is, in some sense, performing the life they intend to have. The art world especially is full of people who are not yet what they claim to be but are working very hard to become it.

Delvey fit into that theater perfectly.

II. The Vision

The striking thing about Delvey was that she didn’t simply want to attend the art scene. She wanted to build something inside it. Her idea was the Anna Delvey Foundation: a kind of private cultural club and exhibition space in downtown Manhattan. It would combine gallery spaces, social rooms, events, artists, patrons, and the atmosphere of a private cultural salon. A place where the city’s creative and wealthy classes might gather.

The plan was grand. But it also had a strange plausibility. New York is full of institutions that began with the ambition of a single person who simply decided that something should exist and then spent years convincing others to believe in it.

Delvey spoke about the project with total conviction. She behaved like someone who already possessed the financial backing required to make such a thing happen. And because she behaved that way, many people assumed the money must exist somewhere.

This is one of the basic mechanics of social confidence. If someone carries themselves like a person whose financial arrangements have already been verified by someone else, most people will not ask too many questions.

III. Hotels

Hotels played a central role in the Delvey story.

Luxury hotels are perfect environments for people living inside ambitious performances. They operate on the assumption that their guests are legitimate. The bill will eventually be settled. The credit line exists somewhere. The guest’s presence itself is treated as evidence of solvency.

Delvey floated through some of New York’s most expensive hotels as if she were simply another wealthy European visitor temporarily residing there while arranging various cultural affairs. The lobbies, the restaurants, the rooms—all of it provided a stage set that reinforced the story she was telling.

Hotels also create a particular social atmosphere. Everyone is temporarily suspended between identities. People are traveling, negotiating, arriving, leaving. It is a place where someone can exist slightly outside the ordinary structures of verification.

For a while, the performance worked.

IV. The Father

Like many figures who construct elaborate new identities, Delvey carried with her a somewhat murky origin story.

She spoke of family wealth. Of connections. Of a background that seemed to hover somewhere between Russia and Germany, between modest beginnings and more glamorous narratives.

Her real childhood was more ambiguous. Her father had worked as a truck driver and later operated a heating and cooling business. It was a respectable, ordinary life. But it did not contain the European aristocratic wealth that sometimes appeared in Delvey’s stories.

This kind of ambiguity is not unusual among people attempting radical self-invention. The past becomes something flexible, something that can be rearranged slightly in order to support the person one intends to become.

In cities like New York, such reinvention is practically a tradition.

V. Dubai

The most extraordinary episode in the Delvey saga took place far from Manhattan, on a trip to Dubai. Delvey traveled there with a friend—a magazine writer who was documenting the glamorous world that Delvey seemed to inhabit. The trip was meant to be luxurious: private villas, elaborate dinners, the kind of extravagant travel that confirms a person’s social status.

For a few days everything unfolded according to the script. And then the bill arrived. The charges for the trip reached roughly $60,000. Delvey’s payment arrangements suddenly failed. The promised wire transfers did not appear. The hotel demanded settlement.

And the friend—the magazine writer who had been invited along for the ride—found herself responsible for the enormous bill. So Delvey left her there. Super bad business Anna baby.

It was a moment that perfectly captured the strange mechanics of confidence artistry. The performance works right up until the moment when reality insists on payment.

Someone, eventually, must pay the bill.

VI. Collapse

Once the financial machinery began to fail, the unraveling accelerated. Banks wanted documentation. Hotels wanted payment. Institutions that had briefly entertained the idea of supporting Delvey’s foundation began to ask more detailed questions about the supposed trust fund that would finance it.

The answers did not exist. The performance collapsed. Delvey was eventually arrested, tried, and convicted of fraud.

VII. The Strange Sympathy

And yet the Delvey story produced a strangely sympathetic public response. Perhaps it was because she had not simply been extracting money for luxury purchases. She had been trying, in her own improbable way, to create something. A cultural institution. A social space. A downtown hub for art and ambition.

The plan was impossible, but the ambition was recognizable. Many people—especially those drawn to cities like New York—understand the impulse to reinvent oneself, to construct a future through sheer force of belief. Delvey simply pushed that impulse far beyond the point where the arithmetic could sustain it.

VIII. Coda

In the end, the most interesting thing about Anna Delvey may not be that she fooled people. New York has always been full of people attempting improbable social performances. The interesting thing is that, for a moment, she came very close to building the life she imagined. And perhaps that is why stories like hers continue to fascinate us. They remind us that the line between visionary and impostor is often visible only in hindsight.

Dedication: For Anna baby (you’re hot BTW) and all the beautiful strivers out there. May your world-curated art spaces someday come true.