Like a lot of anonymous young men in Manhattan, Jonathan Leaf wants just two things from life: to be a famous writer and to marry a pretty woman.
So far, he’s not particularly well known and he doesn’t have a girlfriend. But that doesn’t mean he’s given up. After all, this is New York, where everyone under 50 is secretly convinced that he or she is about to blow up huge any second now. And, at 33, Mr. Leaf has indeed written a play, about the Russian poet Aleksandr Pushkin, that was good enough to get James Wood, the hip literary critic of The New Republic , to have coffee with him. Mr. Leaf is also charming; he listens; he has good manners and the other nice-guy traits. He’s tall, gawky, not bad-looking–perhaps catnip to a certain type of Ivy League woman.
But consider the downside. Mr. Leaf’s posture is really bad. He slouches. He doesn’t dress well, and the ladies don’t like that. Worse, Mr. Leaf lacks the quality New York women adore: confidence. So far in 2000, Mr. Leaf has gained weight and has not had sexual intercourse.
He also lacks another quality women tend to find appealing: money. His father died in 1997, and the small inheritance he received is gone. Presently he has about $1,500 in the bank but owes $20,000 in student loans. He is being sued for $1 Million–a car accident in Morningside Heights.
But things may be looking up: The actress and singer Melissa Errico, who is married to sportscaster and tennis player Patrick McEnroe, met Mr. Leaf through a mutual friend from Yale University who used to sort of stalk her, and she has convinced the Irish Repertory Theater to give a reading of the Pushkin play in September. “He’s a doll,” said Ms. Errico. “I think he’s going to be everyone’s sweetheart, because of his personality. I am totally fascinated by him. I think he needs focus, professional focus.”
Ms. Errico is Mr. Leaf’s only brush with the shiny side of life. He has never been to the Hamptons. He takes dates to the Metropolitan Museum of Art and gets there early so he can purchase two passes for 50 cents. On the way home from a date, Mr. Leaf has the cab drop his date off, then, after taking the cab a more few blocks, he gets out and rides the subway. He gets his New York Times from recycling bins. Home is Flatbush, where he lives with his 88-year-old grandmother, Bessie.
“I lead a very dull life,” Mr. Leaf will tell you. “I’m a 33-year-old man who lives in New York and I’ve never been unfaithful to a woman. I don’t know how many people can say that. I think that’s a small, small number. That’s how dull my life is.”
Early on a recent Sunday evening, Mr. Leaf was in his dining room, vigorously cutting cheese. He was wearing a blue sweater and jeans. He had $12 in his pocket.
“Do you like Cotswold?” he asked. Then he mentioned that he was quite certain that he was neurotic.
“Like the way I’m holding my arms right now,” he said. “Very closed in. The body language is bad. I would say: very bad. I don’t stand up straight. My appearance–I have all sorts of neuroses. My hair looks stupid, my nose is too large, my lips are too large–they go on and on. My voice is too nasal and a shade too high. My hands, the palms. You know, an aristocratic hand should have long, tapered fingers and a small palm. You see, I have this huge palm and these fat stubby fingers. They’re grotesque.”
He’s also accident-prone. “I’ve broken my ankle, my wrist, my jaw, my nose, several of my fingers,” he said. “I’ve separated my shoulder. I’ve injured my knee twice. Two kidney operations.”
Mr. Leaf grew up in Trenton, N.J., the son of psychologists. “I was the third child in three years,” he said. “So I think I was actually a surprise to them. Let’s hope it was a happy surprise.”
At 6, Mr. Leaf scored 211 on an I.Q. test. He attended the exclusive Princeton Day School. “All the kids had lots of money and I was this very neurotic Jewish kid who did not fit in,” he said. “I used to read Shakespeare on the school bus. I wouldn’t say I had zero social awareness because that’s giving me too much credit. I would say less, markedly less.”
Mr. Leaf was cast as the villain in a school musical; his voice was so bad he was ordered to speak his lines. He read a lot and ended up at Yale University, where he drank more than he studied. After college, he worked as a security guard, a shoe salesman, a receptionist, a messenger, a news clipper and a substitute teacher.
After trying to make it as a game show champion in Los Angeles, Mr. Leaf took a year off to listen to Beethoven, read and write sonnets. He wrote a play. “I read it and said, ‘You know, this is a lot better than most of what’s being staged.’ On the basis of that I started to think maybe I should be a writer.” So far he’s written nine plays, none of which have been performed, and a comic novel, still unpublished, about the 1960′s radicals who made up the Students for a Democratic Society.
In between bites of cheese, he said women had been “a source of great pain.”
“I was passionately interested in a woman who was bisexual, and she suggested we get together,” he said. “I’d been interested in this woman for about 10 years, literally. We got together and I proceeded to get drunk on the date and made some comments that she might have misconstrued as being homophobic. She immediately bridled. And I thought to myself, ‘Ten years! What am I thinking ?’”
He told a story about another date: “So we go to this falafel place, she’s wearing this long sweater, and I said, ‘Why don’t you take this sweater off?’ And she said, ‘I can’t do that because I just slit my wrists and I don’t want people to see the scars.’ Then she rolled up the sleeves a little bit so I could see the scars. Then the waiter comes over. I ordered and said, ‘What would you like?’ And she said, ‘I can’t eat anything because I’m bulimic and I’m just going to throw it up anyway.’ And then she took her hand and she started stuffing it down her throat, with the waiter there, to demonstrate. Then I said, ‘What would you like to do with the rest of the evening?’ She said, ‘Well, since I’m an alcoholic, I’d like to go out drinking.’ This is a true story. This was a Yale student, by the way. They’re getting the best and the brightest, you know. I would say that was certainly an unfortunate evening.”
His grandmother Bessie sat down.
“He has a sweet temperament,” she said. “He’s very good for conversation. Very easygoing. We don’t get in each other’s way. He takes care of himself so beautifully. He does his own food, unless I make something that I know he likes, and then he will join me.
“He’s very knowledgeable,” she continued. “If I’m stuck and the ladies are coming over and the floor is dusty, he’ll vacuum on his own. Very aware! He has a friend in California and we chat, and he thinks Jonathan’s a genius: ‘He has to be heard from!’”
Did she agree? “I don’t know,” she said. “I know a lot of people who are very bright.”
I asked Bessie if her grandson brought dates to the house.
“No, nobody,” she said. “You’re our first guest, as a couple.” Then she brought out some macaroons.
A few days later I called Ms. Errico, the actress, to ask her about Mr. Leaf. Ms. Errico has starred in Broadway shows such as My Fair Lady and High Society , and she has a part in the current movie, Frequency .
She said that in addition to encouraging the Irish Repertory Theater to do a reading of Mr. Leaf’s play, she was interested in developing and starring in a romantic-comedy screenplay he had written. She said he comes to hear her sing, and then leaves long messages on her answering machine about how much he loved the performance. She said she found him endearing.
“He unravels right in front of you,” she said. “He gets these flashes of brilliance, he’s really assertive, and then he just unravels. He’s like a mad scientist. He never quite eats when I see him, it’s almost like he’s too focused to eat, because he’s waiting to meet me. But you see, I understand people like that, I’m forgiving of that. I’m not like, ‘Oh, no, he’s not a hot Manhattan File guy.’ That’s cool by me. In fact, that’s probably why I talk to him more than I talk to people who are smooth. He’s not smooth, you know.”
Early one morning a few weeks later Mr. Leaf called me.
“Hey, you ever go pick up babes at Bryant Park Grill?” he asked. We agreed to meet there the next night.
He showed up wearing a white button-down shirt, gray pleated slacks and brown comfortable shoes. He’d taken a job as a copy editor for an online brokerage, with offices in Jersey City, N.J. But the big news was that he had traveled to Washington, D.C., to meet with The New Republic’ s James Wood. Mr. Leaf had sent the Pushkin play to an editor at The New Republic , who passed it on to Mr. Wood. The two men ended up in a coffee shop. Mr. Wood said he found Mr. Leaf to be “a slightly romantic figure, because he has this sort of slouching, rather intense, sort of a hero-from-Dostoevsky kind of manner.” He also liked the play. “He’s pulled off the rare achievement, in the modern age, of writing convincing verse drama which is also good dramatic speech,” said Mr. Wood.
At the Bryant Park Grill, Mr. Leaf said there weren’t too many people like himself, attempting verse drama. “I mean, I’ve read Dryden’s verse plays, I’ve read Shelley’s verse plays, I’ve read Browning’s, I’ve read Tennyson’s, I’ve read Eliot’s, Byron’s–they’re almost all terrible.”
Around us, the after-work singles were checking each other out as techno music played in the background. Mr. Leaf was ready to prowl. He explained his strategy: approach a woman he is attracted to, and claim that his “friend” thought she was incredibly beautiful and wanted to meet her. He wasted no time chatting up three women. I asked them for their impression of him.
Paula Karstens, a 32-year-old director of a technology stocks division at CIBC Oppenheimer, said, “I see a lot of violet in his aura.”
She was wearing a revealing pink silk shirt, a pair of tight silk pants that she said she bought in Rome, and high heels.
“You know, Paula,” Mr. Leaf said. “I don’t know if I’m going too far afield, I don’t know if I’m advancing a view that’s questionable or dubious in nature, but I think you have some instinct towards mocking.”
Mr. Leaf spotted someone else and walked in her direction, saying, “This woman is stunning.”
I showed Ms. Karstens a copy of Mr. Leaf’s play. “So is he really brilliant?” she said. “Because I love brilliant men. I need a new boyfriend. Is he gay? Does he have a girlfriend?”
She called her girlfriends over. “I’m reading a play by my new boyfriend!” she said. “I like his name. Did he change it to become a playwright?”
Mr. Leaf returned, carrying two whiskey sours.
“Jonathan, I read this play, I think it’s brilliant,” Ms. Karstens said. “I have one question, though. Do you think it might go over people’s heads?”
Mr. Leaf gave her a look and walked off, apparently to deliver the whiskey sours. He was soon in conversation with a 23-year-old blue-eyed brunette named Elizabeth Drennen, who was with two girlfriends. Mr. Leaf did his spiel–his friend thought she was beautiful–and was invited to sit down. He focused on Ms. Drennen. She said she was from Birmingham, Ala., that she used to be a Sunday school teacher and was now a publicist at Time Warner Books. She asked Mr. Leaf for his age.
“Oh, my boyfriend’s 34,” she said. “He’s great and really wonderful.” She added that they were taking a month-long break.
“I, unlike the rest of these people, am not of Christian faith,” Mr. Leaf said.
“O.K., you’re what, Jewish?” Ms. Drennan said. “That’s O.K., Kevin’s half-Jewish.”
Mr. Leaf told her she was beautiful but would look better with glasses. “Do you wear glasses?” he said. “You know, there’s a positive correlation between nearsightedness and I.Q. I have perfect vision.”
Mr. Leaf got up, and the women discussed him.
“I like him,” Ms. Drennan said. “He’s adoring. He’s insightful. He’s definitely not a Shylock, with his comments. He’s definitely tricky. Totally a line-er. A tricker. But I tell you what I like, and this is me, and I’m sure all women are like this, but he gives a lot of attention. Men who give you attention–love it, you just love it. Where is he?”
Mr. Leaf had gone back to Ms. Karsten. She was imitating a geisha.
“My name is Shi Ho,” Ms. Karsten said. “I’m from Kyoto, Japan. I’m a geisha. We really, really like to give a man pleasure! We pour the sake, hee! Hee-hee-hee! And then we give massage .”
Mr. Leaf disapproved. “Remember that guy who got fired from Morgan Stanley for those nude pictures?” he said. “You keep talking, that’s what’s going to happen.”
“You’re fascinated by me,” she said.
Mr. Leaf confessed that he was.
Ms. Karstens began dancing a jig, stomping loudly. Then she backed up against Mr. Leaf and rubbed herself against him. Head on his chest, she looked up and asked him for a light. Steadily, Mr. Leaf lit her cigarette.
“You know what’s amazing?” he told her. “It’s how sexually confident your body language is and how neurotic mine is.”
Meanwhile, Ms. Drennen and her friends were still talking about Mr. Leaf.
“Why does he slouch?” Ms. Drennen said. “He shouldn’t slouch. If he sat up straight and acted like he was, like, more of a man , people would sort of gravitate towards him more. Act like somebody and you will be somebody. I love confidence. Dishonest or not, if you pretend to be something, eventually you will become something.”
Later that night, Mr. Leaf went home to Flatbush alone.
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