Girl Trouble

One of my weirder New York dating disappointments came right after what I thought was a pretty decent date. Two days after getting fixed up by a friend, I called to thank her and – I must admit – troll for information on a woman who had turned out to be cute, smart, and funny.

Well,” my friend said with the requisite amount of diplomacy, “I think she had a good time, but I’m not sure you’re her type.” Fair enough, I thought. “She’s looking for more of a …”

As she paused, I began making a mental list of my shortcomings. Tall guy. Buff guy. Less neurotic guy.

“I guess more of a Skadden, Arps guy.”

For those who don’t keep score, Skadden, Arps – actually Skadden, Arps, Slate, Meagher & Flom – is the white-shoe law firm that had then just begun sharing a building with Condé Nast; those who do keep score had been speculating about how many of its junior partners would soon be sharing more intimate space with Vogue’s junior editors. Not because Skadden, Arps guys have a reputation for being particularly tall, buff, or funny, mind you. Simply because they have a reputation for being particularly wealthy.

Which is fair enough. Women have always been attracted to powerful men, and the majority of men who move to Manhattan eventually resign themselves to a less interesting romantic life than Ron Perelman’s. But even hovering around 30, I’m old enough to remember a time when it seemed considerably more fashionable for women to talk about their careers, feint toward the check, and at least act interested in guys who summered in the East Village instead of the East End. Marrying for money was considered retrograde, dating for dollars something that simply wasn’t discussed. Of course, that was when you could buy a one-bedroom for $150,000.

These days, twenty- and thirtysomething women have made a sport – as well as an hit TV show and several briskly selling books – out of complaining about New York men. Too short. Too fat. Too bald. Quick to judge, slow to commit. Which is also fair enough. New York City has always been a beacon for those looking to climb to the Top of the Heap, and men and women here don’t want to settle for less than perfect in a life mate any more than they want to settle for an apartment without a Park view or a job that won’t pick up the tab for lunch at the Grill Room. Instead of having a fine old time looking for Mr. or Mrs. Right, New Yorkers comb the city for Mr. or Mrs. Perfect with the same intensity – and the same inevitable disappointment – they bring to searching for the ideal apartment.

I remember a time when it was fashionable for girls to at least feign interest in guys who summer in the East Village instead of the East End.

Only these days, Mr. Perfect often seems to come with the ideal apartment. On Sex and the City, the fantasy figure who captivates the characters isn’t Mr. Cute, Mr. Buff, or – despite all the talk about the show’s woman’s-eye view of sex – Mr. Hung. It’s Mr. Big. In Candace Bushnell’s Four Blondes, Mr. Big looms even larger: A model sleeps her way into her dream houses, a marriage begins to unravel when a husband stops pulling his career weight, and at the end, happiness is a warm venture capitalist. Nor is this an attitude that’s limited to 10021: Lil’ Kim eerily echoes Bushnell’s fascination with Manolo Blahniks and the men who might pay for them. Do I even need to mention Who Wants to Marry a Multimillionaire?

Does Sex and the City imitate life? Does life imitate Sex and the City? (Am I just getting older?) Either way, one can’t help but get the impression that more people are keeping score – or at least talking about it a lot more often. To the extent that they are, Ron Perelman has a solid lead. Like most guys in Manhattan, I’m more like Mr. Middle. I have my own apartment (small), car (old), and suit (inexpensive). I go out to dinner a few times a week and take a few vacations a year, both to places best described as funky. In Boston, from what friends tell me, I’d be a catch. Amid Manhattan’s minefield of surgeons and software barons, I sometimes can’t help but wonder if certain women are looking at me as dead weight they’d get stuck hauling to the Top of the Heap.

Like every other Mr. Middle, I have my war stories: There was the artist I met at an Internet party who proceeded to grill me about the host’s net worth; the blind date with a gender-studies major who told me how hard it was to survive as an independent woman in New York, then asked me what editors I could introduce her to; the woman I met at the bar in the East Village – the East Village! – who heard I was a magazine writer and asked me if I thought I’d ever get anything published in Vanity Fair. Years ago, when I went on a few dates with an aspiring model, she suggested we spend a Saturday shopping for clothes. I agreed, but I had to back out when I got the distinct impression her idea of going shopping consisted of me buying her outfits I couldn’t even come close to affording.

What’s weirdest to me is that all of these women have good jobs. None of them seem to really need more money. (Do models really need new clothes?) They’re neither wealthy enough to have gotten used to the good life nor underprivileged enough to have to worry about it. In short, they’re the kind of women who a few years ago might have been talking about their careers, their independence, and their conflicts between making vice-president by 35 and having a kid by 40. Now they talk about meeting Prince Charming. Preferably with a castle in the Hamptons.

Could there be an odder time to bring back the dating customs of the turn of the past century? Yes, women still make less than men in the same jobs; yes, they’re insecure about their chances to balance careers and families; but as Sex and the City seems to delight in pointing out, they no longer feel the need to be in a relationship to enjoy a weekend away, raise a child, or even have satisfying sex. At the same time, many women don’t seem satisfied without a partner. Which is fair enough. But why does it have to be a senior partner?

Girl Trouble