Chapter 14 — A desperate move, a mistake, and a wreck that made everything worse.

An Ordinary Disaster — chapter 14 — How to Make an Actual Life Error

Celebrating a successful conference in Tallinn

Three-quarters of my way through the masters program in Urban Planning at UW Madison, I had the chance for a quick trip back to San Francisco. Along with my coursework, I had an R.A. job on campus sixteen hours a week and the beginnings of a conference business up and running, but when a quick consulting gig popped up, I was happy to jump on a plane for a free trip back home, not to mention the extra cash.

Knowing that I’d be in town for a few days, I did what I’d often do in those days and dropped a note to someone that I felt would be open to getting together. Jenna was a woman that I’d dated for a while in my twenties after meeting in the sweaty downstairs disco basement of a joint called Nickies on lower Haight.

Along with that Swedish chick that I pulled from Vesuvio, Jenna was one of the few women that I’d ever met in a bar. I was always pretty useless at meeting people that way, but there were a few, and in this case I’m proud to say that I remember her saying that it was my dancing that prompted her to give me her number that first night.

I flew out on a Thursday and we met for dinner on Friday. I hadn’t seen her in some areas and when she showed up, I was floored again by this striking, strong woman—still something of Marlene Dietrich meets Bettie Page, now grown into herself, with lithe, athletic sheen to her skin.

When we’d split before it was copacetic, and at this point we both had a few years of real adult life under our belts. I think we were both impressed with each other. She’d been doing triathlons and had what sounded like something of a career going, and my story sounded pretty good too, between grad school and the business I’d started. I didn’t get home until after midnight, and I was feverish with excitement.

The very next day, I found myself walking around Hayes Valley with my buddy Rich on one of those warm, bright days of late spring that always reminds me how much of a maritime city San Francisco really is. The sun was out, and I was enjoying the fresh sea air rolling down the hill from Alamo Square as I cruised happily down the sunny side of street, on my way to one of my favorite little shops where I’d become acquainted with the owner.

Scanning down the block, my eyes connected with a familiar set of curves. Long, wavy chestnut hair, jeans tucked into motorcycle boots, a saucy set of lips set below eyes just a little bit too close together. I’d just seen her the night before, and it took me less than a second to see that is was Jenna again.

Her eyes crossed my path as I watched her swinging down the block, and a wide smile broke across her face like a wave.

We’d left dinner the night before without any plans to be in touch, but as a visitor to San Francisco for a change, my heart swelled at a familiar face on the street, and it sure seemed like something sweetly meant to be when we bumped into each other like that.

* * *

Back in Madison, I was a year and a half in, and the only part of the question of what I might do once I was finished there that had become clear was that I wasn’t at all cut out for a job as a city planner. I’d figured that planning might be a way to put my interest in urban geography to work in a practical way, but after sitting in on just one of those interminable public planning review meetings, I’d had enough.

Bureaucracy sure ain’t my thing. I’d been looking at my other options, and at the same time, the series of conferences that I’d started in ’99 had begun to spin off a little income without even too much work on my part. In the meantime, my life on the ground there was A-player grad student by day, and dirty as dirt got by night.

Although I’d gone out to Madison in partnership with yet another girlfriend, we split not long after we landed there. Reverting from vanilla boyfriend to sex-focused boozehound, I set up my usual shop on the usual sites, and before too long I managed to meet the one female person in town with similarly straightforward obsessions.

Lola was just like me—an over-sexed, dedicated drinker with a day job that kept the lights on, but who lived mostly at the keyboard, and more at night than out in the daytime world. She was a bit of a writer, and had a Tumblr site where she posted anonymous accounts of her exploits in the sexual underworld. I was actually doing a little bit of the same—blogging, it was called in those days—and we connected immediately over our love of peanut butter Captain Crunch, Maker’s Mark, kinky sex, and our mutual willingness to put some of our experiences out into the ether.

I’d escaped the street noise and domestic chaos of where I’d been living in San Francisco, and Lola and I got a nice little thing going, which really did help, but I hadn’t escaped the growing unease and disarray of my mental and emotional state. By this point, I was aware that I felt some sort of “depressed,” that is, certainly down more than up, and now with Lola as a steady drinking and sex partner, I was always sleep-deprived and hung over, which just made things worse, week after week.

After a night with her I’d roll out of bed with just enough time to french-press a large cup of over-strong coffee, my head not so much splitting as melting in sickly, slow green fire, push myself into the shower, and then, rejuvenated enough to greet the day, jump on my Vespa to ride across town to campus. I already stood out enough as one of the few people in the program over thirty, and I’m sure my outfit of cut-off, rough Ben Davis work pants, bleary, bloodshot eyes and a whiff of sex and hard alcohol from the night before only reinforced the impression that I was perhaps better left alone.

I sort of had it going in all directions all at once. Work and grad school were going pretty well, I was teaching sailing at the club on the lake, I had a steady girlfriend and I was even going to yoga some afternoons—and, I was drinking and up late every night either with Lola or online, and seeing a campus shrink, none of which was enough to compensate for the hole in my heart that kept getting larger.

To top it all off, just before going to San Francisco I’d been up to northern Wisconsin for an idyllic weekend with my grad-school friend Jamie and her two young kids. Jamie was like a sister from the start, and it was always platonic between us—and we were close from the start, and still are. One day she and I took her son and daughter—both still small enough for me to pick both of them up together, one in each arm—on the ferry to the Apostle Islands, a tiny, verdant archipelago extending out into Lake Superior. It must have been a weekday. On the way back, we found ourselves as the only passengers on the old square ferry as it cruised slowly back towards the town of Bayfield in the brilliant late-spring sunshine. I led the kids up the steep stairs to the open door of the pilothouse, where the captain beckoned us inside. Minutes later, first the five-year old girl and then the three-year old boy took their turn at the helm of the hundred-ton ferry boat as both of us adults encouraged them to look back at the wake to see how they were actually steering the thing back and forth. It was just a moment, but that was a powerful glimpse into of what being a husband and father might be like, and a very dramatic contrast to the manic, unsettled pace of my daily life.

* * *

All of that’s to say that running into Jenna that Saturday back in San Francisco felt incredibly serendipitous. I was hungry for an out—and to prove that I could join the ranks of men who’d found a good woman willing to be their wife. Even though I was more and more comfortable in the sexual underworld, at the same time I wanted to know, and to show that I was not a bad man but a good man—and as far as I knew, to do that, I had to “commit,” which seemed to be shorthand for signing up to do what you really didn’t seem to want to do, but sort of knew that you “had” to do. I was also desperate for connection, for stability, for normalcy, for being part of something, for family, even.

That was beneath the surface though. What I felt in the moment was excitement, gratitude—and not a little bit of magic—and I have to say, she seemed pretty happy to see me too. We only had a few minutes together there on the sidewalk, but I was used to making things happen, and so before she slipped away, I suggested we that have dinner again while I was still around—and why not that very night?

She said yes, and I was walking on air as Rich and I continued our tour of the City. Passing Tiffany’s downtown on Grant Street an hour or so later, I was hit with a crazy idea—and by the time that we met for dinner, I knew what I was going to do.

Jenna and I met for dinner in a place that I chose because it was in a part of town where I’d always wanted to live. Potrero Hill was certainly not the fanciest but one of the oldest and most characteristic neighborhoods of the City, with views of the skyscrapers in the financial district, out to the cargo anchorage south of the Bay Bridge, and across to port of Oakland. We sat together as old friends, feeling the warmth of connection rekindled as I worked up my nerve.

I was determined, and I knew from not only my working life but also from my many interactions with women that there was a certain sorcery in that conviction. After paying the tab, we walked up the hill to take in the view, and I knew that while what I had in mind would be surprising, she wouldn’t reject me. As we stood on the quiet corner of Carolina and Southern Heights, taking in the view and reminiscing about our love of San Francisco, I came out with what had come to mind earlier that afternoon.

“Here’s what I’m thinking, Jenna.” I took a breath, not in hesitation, but because I could feel the weight of the incantation that I was about to speak.

“You and I should get married.”

“What? Wait. Are you serious?”

She was shocked—and delighted. She laughed gently, already digesting the possibility.

“What about your masters?”

“I’m not gonna be a planner. My business is doing well enough that I can come back here, we can get a place right on the Hill, and I’ll be happy, together, with you.”

She was thinking, but I could tell the spell was working.

“You really think we should?”

I already had my stake in the ground. “Yes, I do. That’s what I want to do. That’s what we should do.”

She called me the next morning and I went by her place on my way to the airport. She accepted my proposal, and better than ever at doing, and still completely cut off from feeling, I went back to Madison, packed up my apartment, flew off to Europe for one of my conferences and then back to San Francisco, found an apartment for the two of us, and within a matter of less than six weeks we were shacked up together three blocks from where we’d had dinner, as if that had been the plan all along.

The truth of it? I’d say that I have no idea, but that isn’t true either. The truth was that, just like my parents had when I was a kid, we both avoided the truth even when it was staring us in the face. After all, Jenna and I had been together for at least a year in our mid-twenties and ended it cleanly because it was obvious that we didn’t have enough gas back then—so why would we now?

The truth of it was right there for us to see from the start, but we insisted on ignoring it. The truth of it was also right in front of me during a short encounter that occurred on my trip to in Europe before returning to join her in San Francisco.

I flew to Tallinn, a stunningly preserved medieval merchant city guarding the eastern reaches of the Baltic Sea as it stretches eastwards towards the Russian city of St Petersburg. It was the summer of 2004, and I’d chosen the location because Estonia had just joined the still-nascent European Union and I wanted to see the place before it was swamped with British weekend stag-and-hen partiers, and to bring our business there as a sort of congratulations to the Estonian people.

The conference went off well, even through this was only the second or third one that I’d organized overseas. On the final night, I went out to celebrate with a few of the participants, themselves all young Londoners who were already savvy to the party potential of this attractive place that was just an hour’s flight from the UK. Along with being inexpensive, like many Eastern-European countries Estonia was also known for attractive women, and the subject was on my mind as we finished dinner and stumbled out into the streets, lit by the glow of the late night mid-summer sun hanging just barely below the horizon. Not wanting to be observed in my pursuit of flesh, I made a point of losing my companions and before long found my way into the vast cave of a strip club.

I was half drunk, and my usual backstop of a tab of Tramadol blurred my perception in a way that I enjoyed at the time. I wandered through a dark maze packed with bodies, a small theater, a balcony, many doorways, lights and shadows. Growing weary, I ended up by myself in a dark downstairs booth, drawing the curtain closed behind me.

Despite my fervent interest in sex of all sorts, I hadn’t been someone who pursued dancers, strippers or prostitutes, and along with my state of inebriation—and very much aware that I’d just announced to everyone back home that I was going to be moving back to San Francisco and getting married—and that the woman who was effectively my fiancé was waiting for me there while I jetted off to Europe, and already having sensed the unreality of what I was getting myself into at home, I was in a wretched state of denial, and already beginning to despair at my dilemma. I didn’t know what I wanted. I thought I wanted to get married—and I also wanted to at least see what had been advertised on the posters outside the club.

A hand appeared and pulled back the curtain, revealing an arm, shoulder, breasts, and then the body of a young woman, who smiled and slipped into the booth with me. She couldn’t have been more than nineteen, and there couldn’t have been more contrast between us as we arranged our limbs in the tiny stall, pretending it was all natural enough that she was sober, slim, and entirely naked, and I was bleary, bloated, and spilling out of the suit that I’d bought just a few days before on the same block in San Francisco where I’d run into Jenna.

I just sat there goggle-eyed and immobile.

I’m sure it wasn’t the first time the person tangled around me had gathered that a client of hers felt conflicted. Finally, she broke the awkward silence and asked, “what do you want to do?”

I didn’t even know what might have been allowed, and I was too drunk for sex anyhow, but my situation back at home was so much on my mind that I thought she was somehow referring to that.

“I’m getting married,” I said, “I just want to look.”

She recoiled to create space between our bodies and turned her eyes back at me. They flashed unearthly neon blue, her skin glowing radioactive in the UV light—and then she shook her head, palmed the cash the I offered, and slipped out through the curtain, leaving me there in the dark.

* * *

Jenna and I were both very clearly hoping for a Hail Mary into family life. We knew it wasn’t meant to be—we just couldn’t bear to admit it. The week after my trip to Europe, I was back with her in San Francisco in her little Presidio apartment, and to her great credit she did come out and ask, “Do you really think we should do this? We don’t have to go through with it, if you have any doubts.”

I did very much have doubts, and I knew what she meant was really something more like ‘I wish I had the courage to tell you that I have some very serious doubts here. In fact, all I really know is ‘no,’ but I’m afraid to say that, and so I want you to say it,’ but I didn’t have the balls to do anything but insist that we carry on, just as I had when I first proposed.

She also told me that she was taking antidepressants, and asked how I felt about that. What could I possibly say, other than “no problem, of course?” I’d considered doing the same myself that same year, and I was still unclear enough on my own depression and how I felt about pharmaceutical intervention that I swept right by the whole subject, even though it should have been a major red flag.

I should have turned around, closed the door and split back to Wisconsin to finish my bid at grad school. Instead, I said, “Don’t worry, it’s gonna be great,” even though I knew even then, without a shadow of a doubt, that it was going to be about as great as when someone says “This won’t hurt a bit,” right before they land a right hook to your jaw—and that when someone says “don’t worry,” that’s often reason enough to do just that.

The feeling of home is deadly attractive. I doubled down, dropped out, and ran for what seemed like home—and less than a year later it was over, she was gone, and I was alone again.

It wasn’t losing her that hurt so much. We never really had all that much of a good time together unless we were drinking anyhow, and even then, lemme just say, I’m sure it had a lot to do with me as well, but this girl, she seemed cold, sharp, and hard. She had her reasons, but that didn’t help. We were both depressed, and I can only conclude that she must have been feeling as hopeless as I did, because why else would she have agreed to such a dumb-ass moonshot?

What fucked me up about Jenna was losing the story—or how the story changed from a happy, romantic accident that included the ridiculous fantasy of getting married and having a happy little family together to the reality of the fact that I’d been desperate enough to betray myself again, dropped everything for an illusion and a lie, really, and chucked it in together all the while knowing better—and then suffered through a full year of very painful dissonance, including the pathetic joke of several couples therapy sessions which only served to emphasize how deeply committed we were to deceiving ourselves.

I remain convinced that the only way to make a real mistake in life is to knowingly contradict your intuition, and that’s exactly what I did, yet again.

Even though we were both complicit, I felt at fault since the whole damn thing had been my idea in the first place. I ended up minus not just a diamond and a check to help her get back on her feet, but also with a big stain on my mostly-imaginary vision of myself as a husband with a wife and family. I was a fool, the proposal was an error, and the engagement was a wreck.

That story, the real story, hurt bad and it hurt for a long time. Somehow I’d managed to fail to commit on both ends, having quit my masters program and then also this dead-end engagement—and even just the fact that I’d have to admit to having been engaged and not married for the rest of my life seemed like a pretty shitty card to have dealt myself. Once again I’d gone purposefully into the zone of confusion, and once again I’d given up my own path for someone else’s, and my reality for some invention I cooked up somewhere else, with someone that I already knew that I didn’t love enough.

I couldn’t believe that I’d been down so much of the same road before, with Julie in Ann Arbor and Seattle—and at the same time I knew exactly how it had happened. I’d lied to myself and everyone around me, and again I’d persisted in trying to force things into a configuration that I could see very clearly it was not going to take the shape of.

We both felt like shit, and I was wracked with remorse and shame.

Other than empty congratulations, nobody said a word to me when I announced that I was going to drop out and move back to San Francisco to get engaged to an ex. Nobody asked me anything, or questioned me, or suggested that I think about it, or wait, or reconsider. Nobody said a word.

So much for grad school.

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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

Here’s the table on contents for the memoir. You might also enjoy some of my other work, such as

or any of the other essays that you can find here

What does this bring up for you?

1. Have you ever made an actual life error? I’d love to hear your story! And, how did you recover from it? What did you learn?

2. What is your own relationship with your intuition?

3. What’s your own experience with marriage, and the pursuit of normal?

Please share, comment, restack, recommend, and click the little ♡ heart right there 👇🏻 if you dig this piece. I’d love to hear from you!