Manhattan Wedlock: Never-Married Women and Toxic Bachelors

Everyone in Manhattan knows a fantastic, never-married woman. Unsplash

At lunch the other day, I was viciously gossiping with a man I just met. We were discussing mutual friends, a couple. He knew the husband, and I knew the wife. I’d never met the husband, and I hadn’t seen the wife in years (except running into her occasionally on the street), but as usual, I knew everything about the situation.

“It’s going to end badly,” I said. “He was naïve. A stool pigeon. He came in from Boston, and he didn’t know anything about her and she jumped at the opportunity. She’d already gone through a reputation. No guy in New York would have married her.”

I attacked my fried chicken, warming up to the subject. “Women in New York know. They know when they have to get married, and that’s when they do it. Maybe they’ve slept with too many guys or they know nothing’s ever going to really happen with their career, or maybe they really do want kids. Until then, they put it off for as long as they can. Then they have that moment, and if they don’t take it…” I shrugged. “That’s it. Chances are, they’ll never get married.”

The other guy at the table, a corporate, doting dad type who lives in Westchester, was looking at us in horror. “But what about love?” he asked.

I looked at him pityingly. “I don’t think so.”

When it comes to finding a marriage partner, New York has its own particularly cruel mating rituals, as complicated and sophisticated as an Edith Wharton novel. Everyone knows the rules—but no one wants to talk about them. The result is that New York has bred a particular type of single woman—smart, attractive, successful and never-married. She is in her late 30s or early 40s, and, if empirical knowledge is good for anything, she will probably never get married.

This is not about statistics or exceptions. We all know about the successful playwright who married the beautiful fashion designer a couple of years older than she is. But when you’re beautiful, successful, rich and “know everyone,” the normal rules don’t apply.

What if, on the other hand, you’re 40 and pretty and you’re a television producer or have your own P.R. company, but you still live in a studio and sleep on a fold-out couch—the 90’s equivalent of Mary Tyler Moore? Except, unlike Mary Tyler Moore, you’ve actually gone to bed with all those guys instead of demurely kicking them out at 12:02 A.M.? What happens to those women?

There are thousands, maybe tens of thousands of women like this in the city. We all know a lot of them, and we all agree they’re great. They travel, they pay taxes, they’ll spend $400 on a pair of Manolo Blahnik strappy sandals.

“There is nothing wrong with these women,” said Jerry, 39, an entertainment lawyer who happened to marry one of these smart women, three years older than he is. “They’re not crazy or neurotic. They’re not Fatal Attraction.” Jerry paused. “Why do I know so many great women who aren’t married, and no great guys? Let’s face it, the unmarried guys in New York suck.”

The M&M’s

“Here’s the deal,” Jerry said. “There’s a window of opportunity for women to get married in New York. Somewhere between the ages of 26 and 35. Or maybe 36.” We both agreed that if a woman’s been married once, she can always get married again; there’s something about knowing how to close the deal.

“But all of a sudden, when women get to be 37 or 38, there’s all this… stuff,” he said. “Baggage. They’ve been around too long. Their history works against them. If I were single and I found out that a woman went out with Mort Zuckerman or Morty (Letterman co-executive producer Robert Morton)—the M&M’s—forget it. Who wants to be 20th on that line? And then if they pull any of those other stunts, like children out of wedlock or rehab stays—that’s a problem.”

Jerry told a story: Last summer, he was at a small dinner in the Hamptons. The guests were in TV and movies. He and his wife were trying to fix up a 40-year-old former model with a guy who just got divorced. The two were talking, and suddenly something came up about Mort Zuckerman and then Chuck Pfeifer. Suddenly Jerry and his wife were watching the guy turn off. “There’s a list of toxic bachelors in New York,” said Jerry, “and they’re deadly.”

Later in the day, I relay the story to Anna, who’s 36 and who has a habit of disagreeing with everything men say. All guys want to sleep with her, and she’s constantly chewing them out for being shallow. She’s dated the M&M’s and she knows Jerry. When I told her the story, she screamed. “Jerry is just jealous. He’d like to be like those guys, except he doesn’t have the money or the power to pull it off. Scratch the surface and every guy in New York wants to be Mort Zuckerman.”

George, 37, an investment banker, is another guy who sees the toxic bachelors as a problem. “These guys—the plastic surgeon, that Times editor, the crazy guy who owns those fertility clinics—they all take out the same pool of women and it never goes anywhere,” he said. “Yeah, if I met a woman who had gone out with all those guys, I wouldn’t like it.

Kids—or Lingerie?

“If you’re Diane Sawyer, you’ll always be able to get married,” said George. “But even women who are A’s and A+’s can miss out. The problem is, in New York, people self-select down to smaller and smaller groups. You’re dealing with a crowd of people who are enormously privileged and their standards are incredibly high.

“And then there are all your friends. Look at you,” George said. “There’s nothing wrong with any of the guys you’ve gone out with, but we always give you shit about them.”

That was true. All of my boyfriends have been wonderful in their own way, but my friends had found fault with every one of them, mercilessly chewing me out for putting up with any of their perceived, but in my mind excusable, flaws. Now I was finally alone, and my friends were happy.

Two days later, I ran into George at a party. “It’s all about having children,” he said. “If you want to get married, it’s to have kids, and you don’t want do it with someone older than 35, because then you have to have kids immediately, and then that’s all it’s about.”

I decided to check with Peter, 42, a writer with whom I’ve had two dates. He agreed with George. “It’s all about age and biology,” he said. “You just can’t understand how immense the initial attraction is to a woman of child-bearing years. For a woman who’s older, 40 maybe, it’s going to be harder because you’re not going to feel that strong, initial attraction. You’ll have to see them a lot before you want to sleep with them, and then it’s about something else.”

Sexy lingerie, perhaps?

“I think the issue of unmarried, older women is conceivably the biggest problem in New York City,” Peter snapped, then thoughtfully added, “It provides torment for so many women, and a lot of them are in denial.”

Peter told a story. He has a woman friend, 41. She’d always gone out with extremely sexy guys and just had a good time. Then she went out with a guy who was 20 and was mercilessly mocked. Then she went out with another sexy guy her age and he left her and suddenly she
couldn’t get any more dates. She had a complete physical breakdown. She couldn’t keep her job and had to move back to Iowa to live with her mother. This is beyond every woman’s worst nightmare, and it’s not a story that makes men feel bad.

Roger’s Version

Roger, 39, was sitting in a restaurant on the Upper East Side, feeling good and drinking red wine. He runs his own fund and lives on Park Avenue in a classic six apartment. He was thinking about what I’ll call “The Mid-30’s Power Flip.”

“When you’re a young guy in your 20’s and early 30’s, women are controlling the relationships,” Roger explained. “By the time you get to be an eligible man in your late 30’s, you feel like you’re being devoured.” In other words, suddenly the guy has all the power. It can happen overnight.

Roger said he had gone to a cocktail party earlier in the evening, and, when he walked in, there were seven single women in their mid to late 30’s, all Upper East Side blonde, wearing black cocktail dresses, and one wittier than the next. “You know that there’s nothing you can say that’s wrong,” Roger said. “For women, it’s desperation combined with reaching their sexual peak. It’s a very volatile combination. You see that look in their eyes—possession at any cost mixed with a healthy respect for cash flow—and you feel like they’re going to Lexis and Nexis you as soon as you leave the room. The worst thing is, most of these women are really interesting because they didn’t just go and get married. But when a man sees that look in their eyes… how can you feel passionate?”

Back to Peter, who was working himself up into a frenzy over George Clooney. “The problem is expectations. Older women don’t want to settle for what’s still available. They can’t find guys who are cool and vital, so they say screw it—I’d rather be alone. No, I don’t feel sorry for anyone who has expectations they can’t meet. I feel sorry for the loser guys who these women won’t look at. What they really want is George Clooney. There isn’t one woman in New York who hasn’t turned down 10 wonderful, loving guys because they were too fat or they weren’t powerful enough or they weren’t rich enough or indifferent enough. But those really sexy guys the women are holding out for are interested in girls in their mid-20’s.”

By now, Peter was practically screaming. “Why don’t these women marry a fat guy? Why don’t they marry a big, fat tub of lard?”

Good Friends, Lousy Husbands

I asked that very question to my friend Andrea, 35, a journalist. “I’ll tell you why,” she said. “I’ve gone out with some of those guys—the ones who are short, fat and ugly—and it doesn’t make any difference. They’re just as unappreciative and self-centered as the good-looking ones.

“By the time you get to your mid-30’s and you’re not married, you think, why should I settle?” Andrea said. She said she’d just turned down a date with a beautifully eligible, recently divorced 41-year-old banker because his unmentionable was too small. “Index finger,” she sighed.

Then Anna beeped in. She’d just gotten money to make her first independent film and she was ecstatic. “This idea of women not being able to get married? It’s so small-minded, I can’t even deal with it. If you want to get these guys, you have to shut up. You have to sit there and shut up and agree with everything they say.”

Luckily, my friend Virginia, 35, called and explained to me why terrific women aren’t happy about being alone, but they aren’t desperate about it either. “Oh honey,” she cooed into the phone. She was in a good mood because she’d had sex the night before with a 24-year-old law student. “Everyone knows that men in New York make great friends and lousy husbands. In the South, where I come from, we have an expression: Better alone than badly accompanied.”

This column was originally published in the December 26, 1994 edition of The New York Observer.

Candace Bushnell began Sex and the City as a column in The New York Observer in 1994; it subsequently became a book and a series on HBO. 

Manhattan Wedlock: Never-Married Women and Toxic Bachelors