Should A-List Girls Marry for Love?

So there’s this terrific woman you know living in New York. She’s fun, attractive, smart and has a great job … and is dating a bartender, a waiter or someone altogether unemployed. Some might say she’s “settling,” to use the favored relationship parlance of today. But what if she’s actually a pioneer?

Since the days of Edith Wharton, the feverish class maneuvering that accompanies dating in this city has been well documented. As the story goes, men are continually looking for something younger, blonder and bouncier while women starve themselves, spending a fortune on highlights and bikini-waxing, hunting for the Wall Street banker or trust-fund brat of their dreams.

Frankly, this paradigm is getting a little old.

“The whole idea that all women in New York only want to date up is a little maddening,” said a copywriter in her mid-30’s, who lives in Park Slope and married a carpenter last year (like most interviewed for this article, she didn’t want her name used). “It’s like the bad apples—the modern-day scheming Lily Barts, the ones whose Times wedding announcements say, ‘Until recently, the bride taught first grade at blah-blah,’ or ‘Until last month, the bride worked in guest services at Hooters,’ because now that they’re married, their job is essentially to stand there and look good and be a hot little wife with a personal trainer, dietitian, decorator et al.—are spoiling the barrel.”

A high-school teacher now married to a computer programmer, Allyson is only 30, but a wizened veteran of the pleasures and perils of dating down. “I dated this guy who worked as a land surveyor when I was in graduate school at Columbia,” she said. “I asked him if he liked Billie Holiday, and he said, ‘I love his music!’ Sometimes dating dumb guys and dicking them around makes you feel like a man.”

“I actually like dating men who aren’t necessarily in the same social circle or social class,” said Jessica Coen, the 25-year-old co-editor of the gossip blog Gawker.com. (She declined to get specific about these men and their professions.) “I find it refreshing and relaxing. I think, as women, it feels good to be able to provide for someone, other than childbearing. It’s nice to be able to pick up a tab.”

Memo to Mr. Moneybags: When it comes to the mean Manhattan mating scene, cash alone isn’t necessarily going to cut it anymore. “I dated this guy who was worth millions, and the fact that I didn’t want any of his money made him want me more,” said an attractive and gainfully employed Manhattan blonde, an editor in her 20’s. “It was frustrating for me, because I worked my ass off to make a good living, and here’s someone who’s rolling in piles of money—it was almost un attractive! People acted like I was crazy when I broke up with him. They were like, ‘What’s wrong with you? He’s cute, and you’d be set for life’ …. But how can people actually think like that?”

Dating Down in Tinseltown

Over in Hollywood, men have long plucked beauties from obscurity without anyone batting an eye—Nicolas Cage marrying sushi waitress Alice Kim being perhaps the most recent example.

But flip through the pages of Us Weekly and consider how many A-list lasses are conjoined to B-, C- or even D-list laddies. There’s spitfire actress Reese Witherspoon, who commands up to $15 million a picture and is currently receiving raves and Oscar buzz for her performance as June Carter Cash in Walk the Line, which opens in theaters on Nov. 18. For the past six years, her partner in life and escort on the red carpet has been the handsome yet thoroughly wooden actor Ryan Phillippe, known best for co-starring with his wife in the 1999 snoozefest Cruel Intentions.  Jennifer Lopez, after that spectacular Bennifer flameout, has stayed comfortably under the radar with her lesser-known hubby, the creepy-looking crooner Marc Anthony (the third man she’s married who’s been technically “beneath” her). Megawatt movie star Julia Roberts, who famously never met a co-star she didn’t like or become engaged to, seems to have finally found connubial bliss … with cameraman Danny Moder. And let’s not even get into Britney Spears!

These stars might be secure enough in their alpha-girl status to date men lower down the pecking order, but the media remains suspicious of their unions. The tabloids regularly attribute brewing trouble to issues surrounding the women being more successful than her partner; the men in question are inevitably characterized as sullen, resentful househusbands.

When Hilary Swank was unsurprisingly anointed Best Actress at last year’s Academy Awards, the suspense for many viewers was if the knockout brunette would remember to thank her husband, Chad Lowe, after she forgot him during her last victory in 2000. Ms. Swank, poured into a curve-hugging Guy Laroche gown, got straight to the point: “I’m going to start by thanking my husband, because I’d like to think I learned from past mistakes,” she said, smiling mistily. “Chad, you’re my everything. Thank you for your support. It means the world.” Mr. Lowe, whose thespian gigs include playing an intern allergic to latex on E.R., sat wet-eyed in his tuxedo, clapping emphatically. A month later, when Variety reported that AMC had green-lit the couple’s joint production of Celebrity Charades, Gawker’s Hollywood cousin Defamer quipped, “It’s nice to see that Hilary Swank is using the spoils of fame to keep perennially emasculated hubby Chad Lowe a productive member of society in between infrequent acting gigs.”

If you need more evidence that the zeitgeist is shifting: In Candace Bushnell’s already-optioned new novel, Lipstick Jungle, the women don’t spend their time talking ad nauseam about finding their Mr. Big. They’re too busy worrying about their professions: president of a major Hollywood studio, successful fashion designer and editor in chief of a magazine. Their spouses or lovers may resent it, but they’re resigned to taking the shotgun seat.

‘His Wallet Was Nowhere To Be Found’

Of course, tried-and-true gender roles die hard. A low paycheck isn’t a guarantee against a guy straying, for one thing—quite the contrary, as he might be extra-desperate to prove his manhood. And if a woman is the breadwinner in the couple, she must brace herself for some amount of mockery from friends and family. Some dating-downers interviewed by The Observer told stories of family members sighing in disappointment when told of their boyfriends’ employment status, of friends giving “funny” (a.k.a. derogatory) nicknames to working-class beaux, of having to constantly defend their romantic choices.

“I have this one friend who lives with her boyfriend and a championship Himalayan cat,” said a twentysomething New York woman. The friend is an art director, the boyfriend a low-level office assistant. “I have this joke she doesn’t find very funny, in which I insinuate that the cat brings in more of the rent than the boyfriend does and perhaps she should make him drink out of the toilet.”

Belonging to a “creative” clique doesn’t spare you from outside judgment—far from it. Joni is a photographer’s assistant who recently moved to Williamsburg from the Upper West Side. “I met this really great guy, an aspiring writer, at Blockbuster,” she said. “It was short-lived, but while we dated, my friends referred to him as ‘Blockbuster’ and not by his real name, even after they met him. He actually worked at Borders.” (She recently found a nice fellow “with a great job” in line at the Guggenheim—“but he’s not from New York.”)

Some persist in thinking that dating down is just the much-ballyhooed biological clock at work, egg-freezing technology notwithstanding. This frenetic tick-tock supposedly drives women to grab an available man wherever they can. “I remember a friend once said that whenever she saw a commercial that used that dead Hawaiian guy’s version of ‘Over the Rainbow,’ her ovaries ached to have a baby,” said the copywriter ruefully. Apparently, this often results in dating choices that cause “head-scratching and whispering” among friends.

Caroline, 32, a dark-haired beauty who works in marketing, believes that the old norm of women dating up is fundamentally impossible to change. “There’s pressure to do so, depending on your family and peer group,” she said. “I was once interested in this guy who was the outdoor-pursuits coordinator at a local college. My mother asked me what he did, and she replied with a dramatically disappointed ‘ Ohhhh.’”

Later, she hooked up with a law student. “He had no money and was fine with never doing anything,” Caroline said. “But if I wanted to go out, I would always pay. His priorities were elsewhere, and his wallet was nowhere to be found. I didn’t like the power I had.”

Eventually she concluded, “I have a hard time respecting a man who isn’t ambitious and self-confident. Lots of money isn’t a requirement, but a desire and ability to be financially secure is.”

“Do I want to date someone who can’t get a credit card or drive in 44 states? No,” said an attractive woman in her early 30’s who works in hedge funds. “I don’t want to bring a guy to my company’s holiday party who can’t hold a conversation about anything except the Giants.”

She once went out with guy who worked in telecommunications sales. “Which is a respectable profession!” she pointed out. But “he was highly intimidated by the ‘girl at the hedge fund.’ Everything he did—‘Well, this is probably not up to your standards, Little Miss Hedge Fund.’ Whatever. Another time, I briefly dated an artist. It was just too weird.”

J. Courtney Sullivan, a 24-year-old assistant editor at Allure magazine, has written a book called Dating Up: The Ultimate Guide to Finding the Man You Deserve, which will be published by Warner in February 2006. “My friend and I couldn’t get over how every great woman we know from college—great, smart, accomplished women—date these total schlubs: guys with no money, no ambition, no redeeming qualities and no clue,” she said. The book, however, is not your standard gold-digging manual. “It’s not like, ‘Run off and marry a banker,’” she said. “At the end of day, the most important thing is to be with someone who treats you well.”

For Ms. Sullivan, dating down, while appealing, has its limits. She referred to her own relationship history, with a series of starving-artist types. “For me, it was almost an escape,” she said. “I could leave the office after a stressful week on Friday and relax with one of those guys, bumming around drinking margaritas at Tres Aztecas, listening to him drone on about the one time his band played CBGB’s or whatever, and basking in his no-pressure lifestyle. It was like a little glimpse down the path not taken or something. Of course, eventually this always became entirely maddening and ended in a screaming ‘ Why don’t you grow the fuck up?’ fight.”

Sad to say, women brave enough to date down still face treading a veritable tightrope of male ego. “I’ve had so many guys tell me they wish I didn’t do what I do,” sighed another high-profile editor. “They don’t want to be so-and-so’s boyfriend, or been seen as arm candy. It makes me sad, because I don’t see it that way.”

“Sometimes, dating down is like waking up and looking in the mirror on a bad-hair day,” mused Allyson, the married high-school teacher. “You know you can do better, but you’re just too lazy to try.”

“I think a lot of women who end up dating down, so to speak, are tired of it and don’t want to deal anymore,” Ms. Coen said.

But those women who snuggle up happily at night to their dog-walker stay-at-home honeys? They should be celebrated—not vilified.

“Frankly, a lot of it is superficial crap that has nothing to do with the guy being less of a quality person than the woman,” said Sloane Crosley, publicity manager for Vintage Books and a voluble cheerleader for dating without boundaries. “Most women I know can look past a 32-year-old guy with a massive amount of credit-card debt, bad clothes, a shit job and three roommates in Hoboken—if he makes her laugh.”