Chapter 10 — North Beach in the 90's, Yesterday Boy, and AOL chat.

An Ordinary Disaster — chapter 10 — Thursday Night Whiskey Night

In 1996 I found myself working for a big, pre-internet software company that sent me off on a plane every week to various third- and fourth-tier cities around the country to do what we called “architecture”—designing large, complicated software systems. I’d show up in Minneapolis, Tallahassee and other forgettable, many-lettered places, sleep in shabby, unavoidably depressing long-stay hotels, do my work in grey cubicles, drink in hotel bars, and, for the most part, meet nobody other than the few other guys that I worked with.

I loved being constantly in motion. The work was engaging, and the money was good, but I was flying every week, living on the road, partying on both ends—and, as I soon discovered, all that coming and going didn’t really make for much living. My stories of where I’d just been and where I was going next started to sound the same, week after week, and as I pulled up once again to take the gate 43 bartender up on his offer of a “double for a dollar more” while waiting for my flight to board, it began to occur to me that spending so much time in airport theme bars was the perfect definition of dead-end drinking.

I was living in North Beach, known by both visitors and natives alike as one of the San Francisco neighborhoods that vibrates most with the essence of the city, and by then the internet had been cooking along for just long enough for a few companies to start to situate themselves there, instead of down the peninsula in Silicon Valley. Flying home one Friday afternoon, it struck me that I’d like to find a job that I could walk to for a change, instead having to get on a plane. A fairly pedestrian insight, literally, but it felt good to have a clear feeling about what would be good for me.

People told me that would be difficult, but within a couple of months I’d found a gig with an up-and-coming outfit called Wired that was publishing a flashy new tech magazine and building pioneering sites like HotWired, Wired News, and Hotbot for the early web.

The North Beach pad was owned by a local guy named Mike T., a quiet, sort of shoe-gazing cat with a wry smile and a hip version of a bowl cut who worked as an attorney and ran a tiny record label on the side. He and I shared the top-floor flat with a third housemate, Karen, who was nonviolently bipolar, a bit into Japanese street fashion in the style of Little House on the Prairie meets ’injured nurse,’ and spent most of the time in her room. I had a black-and-white ’74 BMW motorcycle that I used to visit friends around town, and parked it in the ancient, haunted basement at night.

Unlike some others, my friends and I had always pursued drinking as our primary activity, not as an accompaniment to something else. My friend Marc, also a San Francisco native and the son of a old-school NorCal activist and Counterpunch writer, could well have turned out to be just another happy-go-lucky city-league softball infielder and regular belly-up beer-hound, but for his high IQ and leftist DNA, which drew him to a career as a high-level public defender, a noble pursuit which brought along with it with the predictable accompaniment of knowing far too much about the ways of the state. As a result, je wasn’t exactly known as a happy-go-lucky guy, and although we’d never been all that close in the past, in those years we found ourselves at similarly loose ends and wordlessly formed a sort of champion drinking partnership which ran for twenty years of backyard oyster-and-beer orgies, marathon holiday martini parties, and, the highlight of the moment—Thursday Night Whiskey Night.

Now, it’s essentially impossible to find a form of alcohol that I don’t enjoy, but it is fair to say that it’s whiskey that I like the least. Come Thursday—and we would’ve been waiting all week for it—Marc would show up with a bottle of Glen-something-or-other and we’d get started there at home in the glow of the iconic Transamerica Pyramid, which was just down the hill from my house. The evening would start when the bottle was placed on the table, the viscous brown liquor resting there like a menace. As drinkers since our early teens, whiskey was the last real challenge, a bitter syrup that reeked of iodine and smoke that we’d choke down not so much with pleasure but to demonstrate that we were finally ready for—and could afford—what we thought of as a drink for men.

An hour of awkward conversation and we’d have drained the bottle, and then we’d be ready to step out for the rounds. As always, the promise of the night guaranteed some excitement, regardless of what we brought to it ourselves.

We had a set order—Tosca first, then Vesuvio, saving Specs for last, all within a few yards of each other near the corner of Columbus and Broadway. All of these places had been around for at least century or so, and Tosca was the most polished-up of the three, so it was good to step in there while we still had legs. The fantasy was that some out-of-town glam would be waiting at the bar in heels and red lipstick, but mostly it was just us, the bartender and the occasional minor celeb sliding by to the back room. From there it was across to Vesuvio, always tight, everything humming at eleven, the narrow balconies dark and packed with bodies. It was always too crowded for me in there, but we went anyhow out of tradition, and because it was good for tourists.

One night—and only once—we did manage to pull two Swedish girls outta there across the street with us to Specs. I quickly claimed an open table in the back, knowing that would incrementally secure our status with our guests, and the stepped to the bar. The goat-poet drink-slinger, his face lined like old wood, busied his hands as I squinted blearily at postcards from dead sailors tacked to the wall above the bar. When he looked up, I called for “Four Makers, rocks, beers back,” and he lined up a quartet of glasses. “Gimme some cheese and crackers too, would ya’,” and the old smoke muttered, “yeah, yeah, all right” as he tossed the ice, turned for the bottle, poured four across, and then did us the small beers. I carried the drinks to the table and then went back for the cheese, which he carved off a huge wheel with a wire.

The Swedes, I suppose, were pleased to have been shown into one of the better-preserved bits of Frisco nights bygone. Ghosts of stevedores, working girls and pencil-stub writers mixed with the present-day crowd of hacks, sailors and plate-slingers as we drank in the swirl. I couldn’t stomach any more Scotch, let alone the Irish. A sip of bourbon goes down slightly sweet. Every drop feels like it opens the stomach, thins the blood, and makes the view from the inside a bit more agreeable. Follow that with a sip of beer and the cheapest of salty, flaky crackers—just flour and salt, and some fat from the cheese.

It’s late and we haven’t eaten anything else all evening. Everything dissolves together into a mush in my mouth. The beer is going sour and the room is threatening to take me for a spin when I get up to piss. I knock into the doorway as I reach for my pants, focusing on the stapled layers of flyers as pull myself together, standing at the urinal.

The girls agree to leave with us. Knowing that we’ll still be lacking for words, we stop at the corner to buy a pint of Old Crow, as they laugh and totter, helping each other to stay out of the gutter. Shooting a look at the taller blonde, Marc then eyes me to say “that one, she’s mine” as we crash our way back to my flat, where we set up in the living room shooting dice and listening to AC/DC, hoping to impress them with tales of our youth.

After another hour or so I noticed the Swedes silently negotiating with each other as to sleeping arrangements. Sure, I was hoping for some company, but I knew it was up to them, and so notwithstanding—or perhaps because of—Marc’s prior claim, the result was that the one he’d picked went with me, and her friend slept alone—as did he.

The two of us woke the next morning with too much light coming in through the front window facing Vallejo. Bless her, whoever she was, blonde, about 5’5”, sort of a rock ’n roll look—she rolled up from sleep and, despite our triple-malt hangovers, we had a laugh about having ended up in bed, two strangers sailing together for a night in a port city—a story as old as the sea itself.

I couldn’t remember either of their names. “What happened to…?” I asked her, meaning her friend.

“She did not like him so much,“ meaning Marc. She arched her brows, and continued in her göteborgska minimal English. “What was his name…Yesterday Boy?”

Such a perfect little phrase. Clearly, her memory was as foggy as my own. We both had to laugh again.

There was a knock at my bedroom door, and Marc’s voice from outside, asking “You guys want coffee?”

“Heyyyy, Yesterday Boy, come on in,” I called, and he turned the knob to find us still naked and giggling, seemingly at his expense. She meant no harm with her foreigners’ construction, but I could see how the nickname might have stung, and I knew better than to try to make it stick.

Marc did look worse for wear, but we all did in those days, especially Friday mornings after those Thursday nights, knowing that we still had to make it in to work.

* * *

My work was interesting enough, if only because we’d all gotten ourselves very excited over how this web thing was going to change everything, and somehow we were all going to make a pile in the process, even though we were also just as well convinced that it was all supposed to be free—which presented a bit of a problem in terms of the business model. The idea that the punks and the anarchists would win one for once was compelling—and false—but this optimism persisted, at least for a while.

Still, I wasn’t convinced it was really my thing. Although this was long before the tech bros took over, I knew what yuppies looked like—and one of my old buddies mistook me for one of them when he showed up at the office one day to work on the HVAC. I was like, “dude, no, not me!“ even though I probably was wearing pleated khakis and an off-the-rack button-down from Banana Republic. Truth was that I was aware of the conflict of interest, and just as I was happy for the recognition—and the paycheck—I was looking for an out even while I was climbing the first rungs of the ladder. Neon ink and free beer couldn’t cover the fact that we were selling half the screen for blinking banner ads, soon to become the scourge that still plagues what was then called “new media” and is now just about, well, everything.

You may recall that the late-middle nineties were also the era of AOL. Soon to be made obsolete by the web, American Online was right then still rolling on its own massive inertia from the dial-up days, and there was one feature in particular that peaked with AOL and was never really duplicated afterwards—chat rooms. I’d been obsessed with porn since my early teens, and I’d been using dating sites from the start—and of course both of those things had been some of earliest to go big on the web. Chat was nothing new itself, but in the AOL years there was a critical mass, and on any given night there were thousands of anonymous handles roaming and lurking in hundreds of virtual rooms, and anonymous chat made a perfect third of a trifecta with pornography and personals.

I was one of the first generation of digital natives, making side money programming starting at the age of ten. By these years of my late twenties, many of the days that I’d spent already at the keyboard carried over into nights working the same system to different ends. Whether it was from a hotel room in Ohio or New York, or at my own desk at home—still the same art-supply tilt-top from my childhood—the worlds of computers and sex had fully converged, amplified by my long-standing interest in language. Both online personals and chat are ways of doing sex with words, and also of doing it mostly alone, at least until if and when you actually meet someone, which isn’t always the point.

After dinner, at least three or four drinks in, I’d have yet another glass close at hand—vodka from the mini-bar if I was staying at a hotel. Curtains drawn, the room would be dark aside for the blue-grey glow of the laptop screen. Silence. Logged into chat going in one window, I’d often have one of the speciality personals sites like alt.com or bondage.com up in another. Especially after having met an older woman in New York who was deep into the BDSM scene while I was still flying around for my consulting gig, I was gravitating more and more to the edges of sexual interests—and there were and are plenty of sites that specialize in those realms, including Peter Acworth’s kink.com, which had emerged directly from the underground sex scene in San Francisco. Alternating between the three, searching for potential matches in whatever zip code I happened to find myself in, I’d float between chat rooms looking at profiles. Of course they’re all anonymous, and most are made up, but it’s also true that you can tell a lot from what someone says—or writes.

One of the things that you could do in AOL chat was create your own “room,” and you could name it what ever you wanted—no filter. The list of open rooms was the first thing that anyone saw when logging into the adult section of chat. It was a way to catch the eye and direct attention away from some of the more common rooms oriented towards sexy banter or even, let’s say, something like ‘orgy.’ I developed the tactic of entitling rooms in very specific ways designed to lure not a crowd but just one or two people—well—typists? who shared a much more specific bent. I didn’t want to compete with a crowd. I wanted a direct connection.

The most successful of these was a room that I invoked many times over the years called ****-******* ***** *** ***. I’d lurk there, late at night, more and more sedated and also often jet-lagged, compelled to stay jacked in even though I’d sometimes be so tired that I’d nod off for seconds at a time, like a driver falling asleep at the wheel. If you’re familiar with the idea of archetypes, you could say that I was playing wizard here, making an incantation that resonated with only those that could recognize it. Even with my vision gone blurry from exhaustion and alcohol in whatever proportion I’d combined them, I had my wits about me, and enough adrenaline running so that when someone entered the room, I’d be ready to pounce. With a few keystrokes that is. With words and sentences. Still more incantations. Nothing physical. Nothing visual. No sounds. Just words in a box, and whoever was at the other end—which of course was entirely unknown.

If the sparks did fly, the exchange could go on for an hour or more, and I felt proud of some of the transcripts that I saved from those sessions. It felt like I’d created something, and also that I was touching something magic, no matter that it was ‘just’ about sex. All with writing.

These scenes would only get more sordid in the coming years, and I will say that I did feel a bit dirty, but it wasn’t that simple at all. I was well aware that this was not mainstream sexuality, let alone typical ‘relationship’ behavior. It was usually the case that I’d have some sort of actual girlfriend going back at home, but those worlds didn’t overlap much…at first, although then for a while they did. More on that later.

I knew that what I was doing was obsessive and isolating, and it didn’t feel healthy, especially combined with the drinking and the lack of sleep, but there was something else as well. All of this pursuit of various forms of sex also involved a lot of…writing. I didn’t quite equate it with Writing with a capital W at the time, but I was increasingly aware that my intense interest in sex and the creativity that emerged not just online, but also in person with certain partners, felt like a way of being me.

I don’t mean that what I thought of as myself was made up of sex in the main, just that I began to become aware that creating, acting out, doing, writing and being those parts of myself felt like ways of expressing my self. It’s so incredibly clear to me now that communication and self-expression are the primary vehicles of development of the self, and of whatever identity is, and back then, for the first time in my adult life, I felt my own voice emerging. It wasn’t in a way that I had expected it to come about, but there was an unexpected benefit of all that time spent in AOL chat—it was a creative act, and an act of self-actualization.

It was also addictive and avoidant, but the sex wasn’t the problem per se. My obsessive attachment to sex was a problem, but along with that I could finally feel something of myself emerging. In fact, it was the first time since art, writing and language classes in high school and college that I felt my self growing, and I was more aware of it at this point, because of how desperate I was to feel more like someone. Even as the shadow around all that edgy sex continued to grow, some gold was beginning to show through.

* * *

On yet another one of those Thursday Night Whiskey Nights, I was up at three or four in the morning in the living room with a different friend, also named Mark, my roommate Karen and her not-quite-eighteen-year old cousin who was visiting from central valley. I think we were playing Risk, drinking of course, throwing the dice and shouting our moves. I knew we were being loud, but what the fuck did I care? It was clear the country cousin was getting curious, and the volume in the room wound up higher and higher with intoxication and sexual energy. The four of us got louder and louder until my housemate Mike—also the landlord—burst out of his room with pinched, sleepless look. He was stepping down the hall when I stood up to pre-empt his censure. Taking a breath from the excitement in the living room, I caught his eyes gently. “Don’t worry,” I assured him, “I’m moving out—this week,” before wrapping up the board game and leading Karen’s cousin off to my room.

Getting my own place felt like a grown-up move, and I had six-figure job as Director of Engineering to match, but I had other motives beyond making good with Mike. I knew that living alone I’d be more free not just to party at all hours, but also to indulge myself in the world of digital sex, undisturbed and unobserved. I was desperate in the way that addicts need a fix, and a big part of the reason that I decided to get my own place right then was that I knew that it would allow me too do more of what I needed to do, in secret.

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Thanks for reading, and for being part of this journey.

This is part of AN ORDINARY DISASTER, the book-length memoir about a man learning to listen to himself, and the price I paid until I learned how to do that, serialized right here on Substack with a new chapter published every week.

You can find everything from the memoir that I’ve published so far right here.

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Further reading

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