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When I’m with my real parents, I regale them with funny tales of Rich American John—“A woman comes every week to clean his apartment and he pays her handsomely!”—a profligate, silly individual whom we may all safely look down upon. And yet, despite his Americanness, or perhaps because of it, we also respect him. At Thanksgiving family dinners he tries to steer them from their dreams of law or accountancy for me, telling them stories of his own years as a television writer. “And how much money did you make from this writing business?” my father wants to know.

He tells them. “Ooooooh.” It is a fine figure. “Gary’s very talented,” John says to my parents. “He can make it as a writer.” And I blush and wave it away. But I am thankful. A soft-spoken American whose apartment my parents and I have estimated to be worth close to a million 1998 dollars is my advocate.

Later, I realize that just as I tried to puff up my family’s barely existing wealth when I was in high school, I am attempting to make John richer and more generous in the eyes of my parents, my friends, myself. I am trying to make John the parent who would take me right out of Solomon Schechter. The parent who would say, “We can do better than this.” The truth is, John’s father did not own half of Salem, Oregon, the glittering state capital from which John hails, as I always claim to others. He owned a hardware store. The Upper West Side apartment, bought in the mid-1990s, cost John two hundred thousand dollars, not one million. The single Armani blazer he owned and bequeathed to me was hardly the Gatsbyesque wardrobe I made it out to be. And even those trips to Le Bernadin or La Côte Basque were rare. More often than not there was sugar-cane shrimp at the Vietnamese joint around the corner from his house. But, honestly, who cares? I was just happy to be with him.

No, I want the safety of John’s imaginary riches to rescue me from my mother’s $1.40 Kiev-style chicken cutlet. “When you have to pay for everything, you will know that life is hard,” my mother says the night she sells me the stack of butter-stuffed poultry and a roll of Saran Wrap for twenty dollars even.

And I realize then the dissonance between my parents and John. We’re in America, and, frankly, life is just not that hard. She needs to make it harder. For her. For me. Because we never really left Russia. The orange Romanian furniture, the wood carving of Leningrad’s Peter and Paul Fortress, the explosive Kiev-style cutlets. All of it means one thing: The softness of this country has not softened my parents.

At the dinner table in Little Neck on the Night of the Cutlets, John and my parents are discussing what to inscribe on my grandmother’s gravestone. A year has passed since she died.

My father wants to write the English translation of a Russian inscription, which translates roughly as “Always mourning son.”

“But you won’t always be mourning,” says John. “You’ll always miss her, but you won’t be mourning.”

My father looks mildly horrified by John’s pronouncement. He’ll always miss her? What kind of American bullshit is this? His mother has died, so he has to literally be the always mourning son.

My mother has another suggestion for the gravestone. “Always struggling son.” She explains for the benefit of our American guest: “Gary’s father thinks he has to struggle. He has to feel this pain forever. Some people”—meaning our kind—“always want to feel guilty.” She comes up with a few more gravestone inscriptions. “Always painful mourning.” “Constantly painful mourning.”

My father will take John up to his monkish attic space to show my friend the lay of his land. “And here I have my Sony radio. And here is some Chekhov and Tolstoy. And here are Pushkin’s letters.” How happy I am to see the two most important men in my life talking to each other, being chums across the distance of time and culture. That one term, Sony radio, is enough to make me cry cutlet-dense filial tears. John is doing it again; he’s softening my family for me.

Finally, outdoors in his overgrown beefsteak tomato and cucumber garden, the sun setting behind him, my father speaks into John’s camera: “When Gary was six years old he was running on the street, kissing me, hugging me. Now he doesn’t want to hug me, he thinks it’s not necessary. But I need this. I feel lost now. Not only because I don’t have my mother anymore, but because nobody needs me so much like she needed me.”

John and I talk about our parents all the time, me only half listening, or quarter listening, to his stories, him immersed in mine. He points out what I sometimes can’t see through both my rage and my love (at a certain point, the two have become indistinguishable): They paid for my college; they bought me my new teeth so that I could smile. If his father, a successful businessman in Salem, Oregon, could worry about payment at a one-dollar parking lot, what can be said of my mother, a woman born in the year after the Siege of Leningrad was broken?

Empathy is the first part of this parental program.

And then, a managed distance.

The years roll by. 1999. I am dating Pamela Sanders, weeping at the presence of Kevin and his powerful woodworking tools. My novel keeps going through draft after draft. Somebody has to be blamed for all this and since I can’t rise up against either my parents or Pamela, it will have to be John.

For years I’ve been trying to squeeze him dry. To my friends, who never meet him, he is the Benefactor, aka Benny. The thousands of dollars he’s been lending me have been flowing into my caviar party fund. Several times a year, my two-hundred-foot studio is crammed with about as many celebrants, who gorge on the finest champagne and silver-gray beluga that I’ve sourced from a questionable Brighton Beach store. The reason for these parties is always vague. My hairdresser is moving to Japan. My hairdresser is moving back from Japan. “Caviar courtesy of my benefactor!” I shout over the MC Solaar and the happy giggling of my Osaka hairdresser. “Somebody out there really loves me!”

And then it ends. And then John has had enough.

Before the advent of the electronic in-box, I manage to save nearly all the letters and postcards that come my way. A sensible gift of habit, I believe, from my mother, who throws nothing out. Or, perhaps, the inheritance of a totalitarian culture where everything will be used as evidence. In any case, John’s letters to me are at the top of the pile. By the time he’s had enough of me, they are as long as twenty-four pages and they render the truth of my life in those days better than I can.

You are not a child and I am not your parent.

There is practically nothing writerly about your process. Your acute and omnipresent anxiety causes you to function much more as an accountant or a producer, with his eyes on the bottom line and no understanding of how artists function, rather than as a young writer, trying to develop a first novel, a new career. In short, you are as mean and ungenerous to yourself as your parents are; they taught you well.

You are no longer twenty as you were when we met. You are pushing thirty. The wounded child in a defensive rage has become an adult man hurting himself and inflicting pain on others.

You are still close enough to the beginning of adulthood that you can change.

Do you want to spend your life as a frightened angry person taking your deepest fears and problems out on innocent bystanders, as well as on yourself? In five or ten years, you could be a father bestowing upon his children the same kind of misery that you now enjoy. That’s how it works.

Your inability to empathize makes it difficult for you to put yourself in the skin of the characters you write.