One night when I was nineteen or twenty, I sat drinking Rolling Rock beer and smoking marijuana in an artfully squalid Squirrel Hill apartment with a friend who liked to get drunk and stoned and tell you what was wrong with you and what you ought and ought not to expect from a life such as yours. That probably meets the legal definition of an asshole, but I liked the guy, and his opinion meant a lot to me. “Joe the Lion,” I called him, after the Bowie song (A couple of drinks / on the house / and he was / a fortune teller he said / nail me to my car / and I’ll tell you who you are). “You have no tristeza” was his diagnosis of me on this particular evening. “And you never will.” He was not a Spaniard or a Mexican. He was not a native speaker of Spanish at all. A Pittsburgh kid, Slovak on his mother’s side. But I believed he knew what he was talking about—he spoke with unfeignable authority, and his words haunted me afterward for a very long time.

Tristeza means sadness, and common sense would suggest that I ought to have been pleased with his analysis of my life and fate. But he seemed to hold my lack of sadness against me or, rather, to pity me for that lack, and it was not long before I began to regret the absence of tristeza in my soul or destiny. I was by nature (whatever that means) a cheerful person, born into comfortable circumstances during a time of unprecedented plenty, free, male, able-bodied, reasonably clever, fortunate, and willing to work. Socially, things for me had been a bit rough there for a while, but over the past few years I had been doing better in that regard. I had fallen in love, gotten laid, made friends with interesting people who understood the world in terms of abstract Spanish concepts. Now it turned out that I was suffering from a grievous lack of tristeza.

Actually, I was all right with the idea—how could I deny it?—that I was not then in possession of a usable quantity of heroic sadness. It was the part about my never getting hold of any tristeza that rankled me.

My upbringing and the thing called my nature had accustomed me to thinking that if I applied myself and took advantage of my opportunities, there was nothing I might want to become or possess that I could not. Without saying anything to my friend—without ever announcing my intentions to anyone, least of all to myself—I set out to remedy this grave deficit of heartbreak or, as I understood it, of the aura, the ineradicable residue, of heartbreak. I implemented a crash program and, like a middle-tier regional power seeking weapons-grade plutonium, went out and got myself a broken heart.

A study of the available literature—or part of it, since the available literature occupied half the world’s library shelves and three fourths of the attention of its poets—seemed to suggest that one indispensable precursor to the production of tristeza was regret. There were others—grief, exile, loss—and along the way, I might reasonably expect to acquire them or at least get a few leads on their whereabouts. But regret was the one prerequisite for heartbreak that I could hope to ensure a steady supply of. All I needed to do was start making mistakes, but I must do so diligently and clearly, taking full advantage of all my opportunities. I must put my trust in unreliable people, take on responsibilities I could not hope to discharge, count on impossible outcomes, ignore blessings that were right under my nose while expending my youth and energy in the pursuit of dubious pleasure. I must court disappointment, miscalculate, lie when the truth would serve better and tell the truth when the kindest thing would be to tell a lie. Above all, I would have to stick to a course of action long after it was clearly revealed to be wrong.

A year passed in much the same way as those that had preceded it, and although I had gotten into difficulties and hurt people’s feelings, lost money, and wasted time, I remained more or less the same cheerful and fortunate person I always had been, not unduly prone to regret, with nothing to grieve and everything still to lose. I had cheated on one girlfriend and been cheated on by another. I had done incredibly stupid things, such as buy gum sticks of hashish from unknown Africans on a scary street in Paris called Rue de l’Ouest. Finally, I had removed myself from the company of Joe the Lion and all my other friends and lovers, decamped to California, and holed up in a rented room in Berkeley. I had started work on a novel that would display to the world the depth and understanding of my sorrowing soul, and at night sometimes I would lie in my room feeling alone and friendless and contemplate the ache in me with a distinct sense of anticipatory pleasure, like a child watching his lima bean sprout on a damp paper towel in a dish.

That fall I began graduate school at UC Irvine, in the MFA writing program. There was a girl I used to see around the English department sometimes, a cute blonde with a gamine face and a Jean Seberg haircut, plump lips, snub nose, big eyes, an air of being fun to be around. One day I saw her, or thought I saw her, in the restaurant of the old student union. She was getting up from the table where she had been chatting with some friends, and as she carried her tray to the trash, I decided to go over and say hi.

I’m not sure how long it took—not more than a few seconds—for me to realize that this was the other blond gamine of a PhD candidate in the Irvine English Department. I had seen her before and had confused her before with her colleague. She was not as pretty as the other girl, and in place of the other’s slightly hardened pertness, she wore a doubtful, cautious half-smile, as if she knew you intended, like the rest of the world, to try to put one over on her, but she was hip to you, she was on to your methods. People had tricked her and deceived her and let her down in a number of ways, and it had left her embittered and a little punchy. She was older than me by seven years, and probably no wiser, but she knew enough, at least, to be on her guard.

It turned out she lived on the Balboa Peninsula, where I was living at the time, and she was just about to head home in her worn old Toyota hatchback. Did I maybe want to catch a ride?

She had a big nose and strong legs and eyes that were an unusual shade of golden green, as pale as champagne—and sad; she was a pretty unhappy girl. I looked at her, this woman who was not the one I wanted to talk to, and I wasn’t even sure if I really liked her much. I remember thinking, as I stood there weighing her offer, This is going to be a mistake.

“Sure,” I said. “That’d be great.”

Eighteen months later, I married her on the back lawn of her parents’ house in Seattle. It was, in a way that I found almost intoxicating—the way slamming a trunk lid on your hand or missing a step as you climb a stairway in the dark can be intoxicating—a great mistake.

I did like her, as it turned out. She had an eye for furniture and flowers, a rich history of weird sex, weird jobs, and weird scenes, an ear for quirky pop tunes. I found that you could make her intensely happy for a little while with a handful of sweet peas or by putting her in a dinghy and handing her a pair of good binoculars and sending her out very early to row softly among the coots and the buffleheads. Most important for me, she had expectations of how a man ought to act and speak and shoulder his obligations, and in the three years of our marriage, I learned how to be a husband.

But she was often miserable—sometimes justifiably, usually for no reason at all—and in a short period of time, I found that I was miserable, too. There were operatic arguments, all-night ransackings of the contents of our souls, drunken vituperations, migraines, rages, grim gray bitter mornings. We traveled, and moved, and bought a house and acquired animals, and engaged in all the standard ploys and dodges, short of having children (thank God), employed by couples trying to outrun the shadow of that first enduring mistake. The first wrong kiss, the first broken fuck, the first harsh word, the first false apology, the first slap and fiery imprint of a hand on a cheek.

Then one spring night I found myself fleeing the house we had bought in all our desperate and mistaken hope for some kind of future together. There had been shouting and tears and a decision to maybe, maybe really, take a little time off. I was steering my car through the rain along a country highway on an island near Seattle, and it was getting dark. It had been raining for days, weeks, months. I had a tape in the player of Te Kanawa singing “Un bel di vedremo,” and there was something about the dreamy stretch of road, the gray light of dusk, the throb of grief in the voice of the singer, the helpless hopelessness of the song, and the long hard stretch behind me of months and years of living with the consequences of my mistake. Something inside me broke, and my face was wet with tears.

I remembered Joe the Lion then, and his prediction that night years before. If he could see me now, I thought to myself. Then I turned off the music, and opened the window, and let the rain come into the car. I drove to the island’s one town. I stopped at the market and bought myself an ice-cream sandwich and sat in the car with the ball game on the radio. At some point I realized, to my horror, that I was perfectly content. I passed a few minutes working my way around the edges of the ice-cream sandwich with my tongue, listening as a wondrous rookie named Ken Griffey Jr. caught the admiration of the announcer and the crowd; just sitting there, fulfilling my terrible destiny.