Meet Doug Elliott of Manhattan

Doug Elliott could be the quintessential successful Manhattan male. He’s in business for himself, as a lawyer, negotiator and entrepreneur. He’s a big restaurant guy. He banters with waiters and waitresses. He goofs with the people at the next table. He’s charming. He dates women like crazy. Men hit on him.

He’s divorced, with a son and daughter. He has a sweet apartment with high ceilings near Union Square. He works a lot, doesn’t sleep much. He plays tennis at Manhattan Tennis Center.

Recently, Mr. Elliott, who is 45 years old, had a little heart attack. He has been doing a decent job of not letting it affect him. He’s still out there, having a good time.

We were in a cab in Greenwich Village.

“I’ve been around so long,” said Mr. Elliott. “I’ve played at all these places. The Back Fence, Kenny’s Castaways, the Red Lion. I’m exactly what I didn’t want to be. I didn’t want to be one of these guys who’s my age, walking around, stopping in clubs where everybody knows me, in part because I’ve just been around so long.”

I came upon Mr. Elliott almost at random: One night, at Marylou’s on Ninth Street, I lost half the contents of my wallet, and he found it. He called me up, and, a few days later, I bought him dinner at Pete’s Tavern on Irving Place.

He said that he had once bedded four women in a 24-hour period. He told a funny story about a famous actor hitting on him. He also gave me his basic life story. Grew up in a small town in eastern Pennsylvania. Married at 19. Attended Yale and Yale Law. Two kids. Divorced. Moved to Manhattan in 1984.

By 1990, he said, he had made a small fortune in prepaid calling cards and a telephone number (900-VIP-SOAP) he created for soap opera fans. For $5 a call, they could hear plot updates from people like Susan Lucci. At one point, he had a three-bedroom duplex off Central Park West, a place in Los Angeles and a limo with a chauffeur. Mr. Elliott blew loads of cash.

Now things are a little less flashy. He’s still making the rounds, though. He said he has some Internet venture in the works. He’s hoping it will net him at least $20 million. Can’t talk about it. Too early.

Mr. Elliott and I met again a few months later at Tavern on Jane restaurant. He told me his Mickey Mantle story.

“I’m sitting there talking with Mickey Mantle,” Mr. Elliott was saying as we shared fried calamari, “and at the time I guess I was the same height I am now, but I weighed about 135 pounds–I was really thin. I had a close-cropped beard, I was wearing a V-neck polo sweater, tight corduroy pants and boots, I think. Mickey looks at me, looks up and down, and he goes, ‘You queer?’ And I said, ‘No, no, no! I know why you’re saying that, because the close-cropped beard–’ ‘No, no, no, just checking. I like to know where I stand with somebody.’ So we talk for about 10 minutes, and I’m thinking, ‘My sports hero is begging me to stay and bribing me with alcohol!’”

The waitress appeared. Mr. Elliott joked with her about maintaining his “girlish figure” and ordered a buffalo burger. Then he told the story about a well-known actor of the stage and screen. In the late 80′s, it seems, Mr. Elliott used to go to Columbus restaurant on the Upper West Side, and one night he bumped into the actor there. Mr. Elliott had some time to kill before meeting his girlfriend, and the two guys ended up watching a video at Mr. Elliott’s place. There was a problem with the tracking, so Mr. Elliott went up to the TV on his knees.

“All of a sudden, there’s these hands on my shoulders, these legs pressed up against my back, and I’m getting a massage,” Mr. Elliott said. “‘You feel really tense, you know what, let me–’ And I was like, ‘Wha–wha–I’m all right.’ ‘No, no, you do feel really tense, let me do this.’ And all of a sudden, there’s a knee in my back kind of pushing me down towards the floor. He’s like, ‘Lay down, man. I know what I’m doing, I know what I’m doing here.’ And I’m like, ‘All right.’ I don’t know what to expect, because we’ve talked about girls and I’m like, ‘Huh?’”

He continued: “All of a sudden, the hands move off my back and move onto my thighs. And he’s like on me, legs straddling, and I went, ‘All right! Ah! Yeah, that does feel better, now that I think about it.’ And I walked over to the couch and I’m sitting, hands on my legs, staring straight ahead.”

Next thing he knew, the actor grabbed his arm and laid his head on Mr. Elliott’s chest. “And he goes, ‘Come on, turnabout is fair play.’” At that moment, the phone rang. Saved by the bell. It was Mr. Elliott’s girlfriend.

Actor Fisher Stevens walked in and sat at a nearby table. Mr. Elliott noted that he had slept with women who had slept with famous men–among them John F. Kennedy Jr., Keith Hernandez, Donald Trump and J.D. Salinger. He calls it his “sharing list.”

After dinner, we went to a Spanish-style bar nearby. I got whisky and he got a big glass of orange juice. He had had the heart attack the week before, and he wasn’t drinking alcohol–doctor’s orders. Next, we went to a sushi place on Bleecker Street, Shiki’s. There was the owner, Laura, who used to give him the thumbs up or thumbs down whenever he came in with a date. She asked him how his sex life was.

“My sex life is always good,” Mr. Elliott said, “because I always have me.”

Later, we went to the Cub Room on Sullivan Street. He ordered an orange pineapple drink, and I asked him about the heart attack.

“I thought, ‘Wouldn’t it be funny if I went now?’ I always joke about, you know, I haven’t reached middle age yet. I probably have another 10, 15 years before I hit middle age, based on my genetics. My grandmother’s still alive, she’s almost 100. So I figure, 45, I’m not middle-aged yet. On the other hand, you never know. Kurt Cobain hit middle age when he was 13. You know, he didn’t know it. And I thought, ‘Holy shit, maybe I hit middle age when I was 22!’ I don’t feel my age. To me, I look in the mirror, and I think this is not a 45-year-old man. It’s at best a 45-year-old boy. I don’t know if I’ll ever be a man.”

He said the damage was “practically nil,” but the heart attack spooked him. He had gotten a liver test and was awaiting the results.

“I was like, ‘Do I have to face my mortality now, or what?’ It was like, this is distinctive. What was going through my mind on a real practical level was, ‘Holy shit, what if I have another one, and this time I just drop dead?’ I wasn’t worried about changing my life style–I was worried about dropping dead.”

He looked over at the young blonde woman next to him. They chatted. Eventually, he made his move: “Monday night,” he said. “Come in here and I’ll buy you a martini.”

On Monday night, Mr. Elliott and I returned to the Cub Room. The young blonde woman had indeed come back. “Hey, Doug!” she said.

Mr. Elliott, with the heart attack now a couple weeks in the past, ordered vodka. He chatted with her for a while, but it didn’t go anywhere

“I’m worried about the liver thing,” he said, sitting down for dinner. “When you’re young, when you’re a teenager, you have no sense of your own mortality. You don’t worry about lines, boobs sagging, not getting it up. Everything is where it’s supposed to be.”

At the table next to ours were two pretty blond women around his daughter’s age. Mr. Elliott shared a pickup technique with me: “You go like this: ‘Excuse me, I hate to trouble you, but would you mind asking that person if they could please pass the piano?’ Something stupid, asinine, that’s my joke.”

Mr. Elliott ordered another vodka. I asked why he always touched my arm as he talked.

“You know, I’m not conscious of it and you’re not the first person to complain. In fact, who’s the guy who’s a writer, majorly gay fellow and well known, older guy, can’t remember his name, here in New York. We’re talking one night, yap-yap-yap, and all of a sudden he goes, ‘You have to stop touching my hand, because I think I already love you and now I don’t think I can leave unless you come home with me, and I know that’s not appropriate.’ Of course, he was waiting for me to go, No, it’s fine!”

One of the girls asked Mr. Elliott for my cigarettes. Conversation began to flow. Their names were Lisl and Jill. Lisl had a fiancé, so Mr. Elliott focused on Jill. She was here from San Francisco for a wine festival. She was wearing a mint green sweater, black skirt. She looked a little like an Arquette, more Rosanna than Patricia.

“Will you have a drink with me later?” he said to her. “Maybe?”

Then Mr. Elliott ordered a filet mignon, and returned to me.

“I know that my behavior’s flirtatious,” he said. “It’s gender-neutral flirtation.” His voice lowered. “I would do the same thing if there were two guys or a guy and a girl sitting next to us. I think what it is, is I have some enormous animal attraction that human beings in general, irrespective of gender, can’t resist. And that’s a burden I have to carry.”

He told a story about a big shot he knows in Los Angeles. The guy hit on him and Mr. Elliott made another narrow escape.

More banter with Jill and Lisl. He tried to get Jill’s number. After some negotiating, he ended up giving her his number. “I want you to know I’m not easy,” he said.

“Right.”

“Did you hear that disdainful response? Talk about a sweeping sexual generalization! She’s going, If you’re a guy, of course you’re easy. Wasn’t that what you meant?”

“How hard it is to seduce a guy?” Jill said.

“See what I mean? I’m on point, that’s why I’m a good negotiator.” The girls were laughing now. “That’s why I’m a distinctive guy, because I’m not that easy, but I’ll play with you this way. If you pulled your top down right now, flashed me, I would think that was funny, silly, and I’d be more embarrassed than you would.”

The conversation died a bit right there. “I think it’s over,” I told him.

“No, no, no, it’ll come back, whenever we want it to.”

Eventually, Jill asked for another cigarette, but there was a lingering unease.

“She’s mad because you asked her to take her top off,” I said.

“Be serious for a minute,” Mr. Elliott said to her. “Did you think I was asking you to flash? You knew I was teasing, right?”

Later, when Mr. Elliott got up and left the table for the bathroom, I asked Jill what she thought of him.

“He seems like someone who’s not used to taking No for an answer. He also seems like someone who thinks that his company is the best reward. To me, he seems like a very typical New York guy. Very forward, very engaging, very up front, shy. But at the same time, maybe not so mysterious.”

After Mr. Elliott came back, he got Jill to accompany us to Raoul’s for caviar; Lisl went home to her fiancé. At Raoul’s, Mr. Elliott was touching Jill’s arm and telling her about the time he accidentally ended up in a gay bar.

“You know who the new gay diva is?” Jill said. “Cher.”

“My buddy used to date Cher! My friend Rob–Rob Camaletti. He was called ‘the bagel boy.’”

At midnight, Jill said, “I can’t believe I’m still standing.” We finished the caviar. Down the street, at Milady’s, Mr. Elliott’s (and Jill’s) Jewish heritage came up. “I don’t actually ascribe to any religion,” he said. “I think religion is really a big cause of most of the grief in the world.”

Jill said she knew he was Jewish right away. “I have Jew-dar,” she said. “I mean, he does, too.”

Mr. Elliott and I played some pool, then we walked her home. On West Broadway, we passed a picture of fat-lipped model Esther Cañadas. “See this girl?” he said. “She used to date the guy who lived downstairs from me, who’s also a DKNY model. Then she moved in and then they got married. They got married!”

“There’s an intelligent couple,” Jill said.

“How stereotypically bigoted of you! Just because they’re models doesn’t mean they’re stupid! It just means they can’t read or write!”

Right then, Jill started making her exit. “Call me, don’t call me, it doesn’t matter,” Mr. Elliott said, kissing her on the cheek. She was gone, trotting up some stairs.

He invited me to his place a few days later. Right as you enter, there’s a life-size sculpture of Batman’s butler, Alfred. There was his pipe collection, his Sherlock Holmes stuff, his chess sets and his video collection ( 9 1/2 Weeks and Bull Durham prominently displayed). On the bookshelf, there was Raymond Carver’s Where I’m Calling From , various Hitler books, Amy Sohn’s Run Catch Kiss , some Tom Wolfe and Martin Amis.

On his computer screen was a short story he had written in the first person as J.D. Salinger. It ends: “Yes, I am J.D. Salinger. Now please–please–leave me alone.” Playboy rejected it but encouraged more submissions. He’s shopping it around.

His two Shih Tzus, Pia and Oona, yipped as Mr. Elliott picked up a guitar and played a sweet love song he composed, “Miles Away,” which begins, “I never thought I’d feel like I’ve begun to feel.” It had a Dan Fogelberg air to it, and when his (excellent) voice got high, Mr. Elliott sounded like Graham Nash.

We left, got into a cab.

“It’s a little weird for me to think that I am at this point in my life single,” he said. “You do get to a point where, ‘You know, I’m not a kid anymore. I may think like a kid, I may feel like a kid, but at some point it’s all gonna end.’” I used to have a thing, I really liked blond-haired, blue-eyed, very kind of WASPy-looking girls, because I grew up on Cheryl Tiegs and I think that gets embedded. It’s like that bonding thing when ducklings are born–whatever they see first they’re attached to forever as their mother. That mold, the model, as it were, is kind of the thing that I like. I used to want someone 5-7 1/2 to 5-8, straight blond hair, blue eyes, about 112 to 108 pounds, little bit of a curve. I’ve eased off a bit.”

The photographer for this article, Nina Roberts, fit his criteria. As she took his picture in the Cub Room, Mr. Elliott was putting the moves on her. MTV personality Kurt Loder was there–he’s another guy on Mr. Elliott’s “sharing list,” by the way.

Back at his place, Mr. Elliott played a slow version of “Eight Days a Week.” Next came Cat Stevens’ “Wild World.” Ms. Roberts asked him to pose on the couch with his dogs at his side.

“Don’t make me look gay,” he said.