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Generation Single

They're frustrated. They're confused. They're ready to give up. But then again, it’s not easy inventing a whole new way to be single. A rollicking rant from the trenches of the Bay Area dating wars.

Olivia* couldn't care less about fly-fishing. She's never frozen her butt off trolling for trout in thigh-deep water, and she has no particular interest in starting now.Yet one Saturday in the not-so-distant past, the 38-year-old biotech saleswoman spent a good three hours at a fly-fishing expo in Marin, perusing the latest in freshwater sink tip lines and quick-release reel technology and, trying not to look too obvious, perusing the guys who were perusing the equipment—all in hopes of replicating her friend Mary's romantic success story.

A year earlier, Mary, a banker, had decided she needed a new approach if she was ever going to find a mate. Her friends seemed to have cool husbands; these solid, ready-to-commit guys must have something in common. So Mary gathered all the Mr. Rights into one room and grilled them. Her conclusion: Great men fly-fish. A float trip to Montana later, she hooked the very attractive Ben, a 44-year-old banker, to whom she is now married.

In this part of the world, it takes a single woman about eight seconds flat to ask a contented-looking couple—even total strangers—how they met. Olivia, for example, had been introduced to Mary and Ben at a dinner party, where she had pumped out the juicy details of their courtship before she was barely inside the front door. Now, two months later, tired of life as a San Francisco single gal—seven years and counting—she figured an afternoon in a convention center filled with rods and reels and the guys who love them might be time well spent. Alas, lightning didn't strike twice. The number of irresistible fly fishermen she met that day: zero.

"What was I thinking?" Olivia says, laughing. "I'm never going to stand in a freezing stream in neoprene waders. But you can't rule anything out—even neoprene."

Welcome to the latest twist on life in the Bay Area—one that should make trend watchers sit up and take notice. In this most experimental, individualistic, alternative of places—America's leading lifestyle lab—sociologists, psychologists, dating experts, and others have detected something potentially worrisome bubbling out of our bedrooms and transforming the culture around us. More than in any other metropolis in the United States, the men and women who settle in this part of the world are having a difficult time finding lasting love.

Of course, this isn't just a San Francisco phenomenon. According to the census, the number of singles is skyrocketing nationwide. In pop culture, the "happily ever after" narrative is in broad decline, eclipsed by the ascendancy of never-weds, from the perpetually, uneasily single girls of Sex and the City to Business Week's recent cover story heralding "The Unmarried America." The trend is especially apparent among thirtysomethings, who have morphed from Gen X into Gen S, for single. As these "gradual grown-ups" (as the New York Times recently dubbed them) have delayed everything from moving out of Mom and Dad's house to saying "I do," singlehood has emerged as an acceptable, even desirable alternative to long-term commitment—and promises to stay that way well into middle age and beyond.

But the story is bigger here for several reasons, starting with the sheer size of the Bay Area's single population. Every year, San Francisco is voted the most romantic American city in polls and surveys, yet roughly 45 percent of the 25- to 34-year-old city dwellers are "never-marrieds," according to the 2000 census. That leaves us behind only the college mecca Boston and tied with the migratory Atlanta. These Gen Sers aren't necessarily who you'd guess they are; the myth of three straight women for one straight guy is just that—a myth. According to estimates based on the same census, unmarried, straight 20- to 44-year-old single men actually outnumber single straight women of the same age by 12,000 in the city. Nor are heteros alone in dating problems; despite the city's reputation as a gay mecca, single gays and lesbians complain they have it worse than their straight friends, if only because the pool of romantic possibilities is smaller.

Indeed, in a poll exclusive to San Francisco of nearly 300 Bay Area singles, almost half  used the F-word—frustrated—to describe their feelings about the dating scene. Especially fed up are the singles we talked to for this report, San Franciscans in their mid-20s to early 40s. Except for singles under 25 (91 percent called the Bay a "good" or "great" place to be single), there's not much optimism. Respondents were almost twice as likely to say the scene is getting worse than better. So, many are opting out: Nearly half of both men and women said they're dating less now than a few years ago, which is why the median number of dates a year was less than five. In this postdating culture, a quarter of women in our poll—including scores who called this a "great" place to be single—went on zero dates last year.

Ultimately, what really makes the story different here is that the Bay Area temperament—driven, eccentric, conflicted over old-fashioned sex roles and gender politics, idealistic, yearning for passionate connection—has made singles here so damn frustrated with each other. You'd think that in a freewheeling dating culture where marriage is an option, not a societal mandate, people would be feeling less pressure and having more fun. Instead, both sexes are in a jumble about how to meet potential mates, the rules of courtship, and what they really want. Men accuse women of being desperate, women accuse men of refusing to grow up, and they accuse each other of being too picky for their own good.

Expectations run extraordinarily high in our overeducated town: According to the latest census, the Bay leads the nation's 20 largest metro areas in the number of single college grads who move here to live (a net migration of 50,000 between 1995 and 2000). When Match.com polled its members about the level of education they considered suitable in a mate, San Franciscans were more likely than people in any other city to say they were seeking someone with a PhD. Yet clearly our expectations are not being met. You'd hope that women and men with the daring and drive to invent a whole new way to communicate using routers and wires would figure out how to open up to each other over a latte. But it's not happening. It turns out sociological shifts are hard not just in the new economy but in the new singlehood, too.

The Meet Market: More Drizzle than Sizzle
When Carrie Bradshaw and her friends want some action, they zip on something slinky, slip into their newest Jimmy Choos, and hit a trendy bar or club. Alas, San Francisco is still in the throes of a postboom nightlife drought. Like many interviewed for this article, James, 35, a cashed-out dot-commer, finds that the crackling, sexed-up energy of the late nineties deflated along with the Internet bubble. Hopping from one launch party to another was a great way to meet new people, he says. Now, singles are falling back on the tried-and-true methods of previous eras—friends of friends or co-workers—and when these are exhausted, few options remain. "It's so disappointing," James says of the change.

But a shortage of venues isn't San Francisco's only problem; the city is also suffering from a bad case of chronic fatigue. Asks Jeff, 27, a private-equity guy: "When did it become the trend to spend Saturday night sober, talking about triathlons?" When over-30 singles do go out, it's apt to be for a movie or a Moroccan Mint latte, not dancing and a sidecar. (In Match.com's survey, coffee beat out cocktails as the most likely first date here; New Yorkers—big surprise—meet for cocktails.) "Men and women are burnt out," says Barbara Dafoe Whitehead, codirector of the National Marriage Project at Rutgers University. "Just coming up with novel ways to meet people—it's exhausting."

Consider our fly fisher wannabe, Olivia, and her friend Catherine, a 28-year-old writer. Both say they're serious about wanting to meet men. Yet neither puts herself on the market. Olivia used to enjoy attending concerts, but these days her friends buy tickets to hear Raffi, the Bing Crosby of the toddler set, not the latest underground band. Even Hiroshi, a 28-year-old single guy who works at Surface magazine, sounds like a 45-year-old suburbanite with a minivan when he describes how he and his friends socialize. "We don't go out to restaurants—we go to someone's place and make dinner," he says. "If we lived in New York, I think we'd be going out. There's a sense of wonder there, that you could meet someone special." So we cloister ourselves: An astonishing 80 percent of men and women in our poll said it's more important to spend time with friends than to date.

Maybe we don't trust ourselves to banter without the help of a spell-check program. Maybe we assume that someone who goes shopping in sweats isn't interested in being noticed, much less making eyes across the Whole Foods salad bar. For whatever reason, in this most politically correct of places, being forward is just so...backward. Chatting someone up in the Blockbuster checkout line is a potential infraction. So is being perceived as trying too hard. This puts Bay Area singles, especially men, in an impossible bind: You somehow need to flirt without flirting, which leads to dating without "dating," which leads to...confusion, cynicism, and Celexa.

"Here, you're supposed to be a laid-back guy in a T-shirt," says Jeff, the equity guy. "Everyone is so damn self-righteous about not being overtly single. You don't get dressed up, you go to Regal Beagle in your fleece. Shit, it gets so boring."

Adds Hiroshi, "You're not going to just go up to someone. In the back of my head I hear the girl telling her friend, ‘Ugh. This guy totally hit on me on the bus.'" These days, he says, he's paranoid about "coming off like a creep." And with good reason: Even at bars—whose major reason for existence, after all, is to loosen up people's inhibitions—Bay Area women have been known to react to innocent flirting as if they'd been groped. Says Marie, a 32-year-old executive recruiter: "If a guy walks up to me at happy hour, I think he's a friggin' cheese ball."

This can't-win atmosphere explains some of the appeal of Internet dating. Online, singles can dispense with the PC dating dance and be brutally direct about what they want and what they don't. In extensive profiles, virtually everything is revealed: dreams, hopes, fears, not to mention height, weight, skin color, college affiliation, earning potential.

This is scoping, San Francisco-style: thousands of men and women holed up in one-bedrooms, anonymously instant-messaging, browsing an endless stream of overpromising, underdelivering profiles. A favorite pastime is checking Match.com for old flames—and laughing at how badly they lied on their profile. If you can stay home and catch The O.C. as you click away, why put yourself out there and let serendipity happen?

A self-perpetuating cycle begins: Uninspired by local nightlife options, trapped in a rut, singles retreat to the web. After expending energy crafting irresistible profiles and witty messages and inspecting "new" inventory, going out with friends becomes an afterthought. All of which siphons the energy and crowds away from bars, clubs, and other traditional meeting places, which just heightens the impression that cyberspace is more action-packed and interesting than your personal reality show.

Occasionally, it is. Carol Cannady, 35, who works at a large local winery, decided to make a husband hunt her full-time job when she left a struggling Internet company two years ago. "In two months, I dated 17 guys, emailed with about 50 more. I kept an Excel spreadsheet," she says, laughing. "Now I'm married and have a kid." We all know someone with a similar tale—it's what fuels the hope that keeps Match.com, Nerve.com, JDate.com, and the rest solvent.

For many others, though, the sites turn out to be yet another largely ineffective tool in their search for a mate. What's more, the psychology bred by online dating can be a trap. The notion that you can know exactly what qualities make your heart soar, and vet candidates by a checklist, suggests love is logical and reducible to an equation. Chemistry becomes an afterthought rather than a starting point. This is the equivalent of the real-life "good on paper" phenomenon: good résumé, good looks, but no spark.

"I went on a dozen dates, but there was no chemistry—none," says Lauren Schwartz, 38, a sassy blond television commercial producer who lives in the Mission. "My issue with Match is that you could have everything in the world in common. But then you meet and—no connection." There is one thing she remembers fondly, though. "You have a dozen guys emailing you every day telling you how great you are."

Which Microniche Are You In?
However you look for love—a bar, a bookstore, a chat room—chances are you run into the same types of people over and over. Despite our reputation for diversity and openness, the Bay Area is, in fact, hopelessly insular, fragmented into microniches defined by neighborhood, class, race, sexual orientation, and hobby—even the kind of dog you own and the car you drive. You can tell a vegetarian Noe Valley protoyuppie Green supporter at ten paces from a Bernal Heights lesbian-mom corporate type.

When singles are hanging out, it's often with the same crew. San Franciscans rarely stray far from their clique. They find a neighborhood and scene that suits them and replay it like their favorite CD. This can create complications. Complication one: When is a date a "date"? Complication two: What do you do when the people you always run into invariably include an ex or two?

What goes around in a microuniverse comes around. When singles meet potential love interests, they have to be doubly certain before making a move. "If you immediately ask someone out, you're gonna shoot yourself in the foot," says Tim, 36, who runs his own software business. "You foreclose on going out with her ten friends. Even one date, you're foreclosed for a couple months. That's the nature of tribes."

Todd, a 35-year-old biotech guy, has been frustrated with how staid his social life has been since the boom ended. "There's a serious lack of new inventory. We always talk about going ‘outside the circle.'" From the looks of things, this attractive former college athlete isn't exaggerating. On a recent visit to his Fillmore Street hangout, the Eastside West, every one of the Seven jeans-wearing women knows him—in some cases biblically, instinct says. His mission to meet "non-Marina, non-MBA types" has involved taking a writing class and volunteering with the Newsom campaign. Only it isn't working. To which his friend Michael points out with a laugh, "If you really wanted to go outside the circle, you'd have worked for Gonzalez."

Gays complain even more about this kind of insularity. After all, the pool of available gays and lesbians is just one-quarter the size of that of available straights. As anyone who's logged on to Friendster will tell you, there's often only one degree of separation between the city's gay men and women. (Steve Pyka, age 24, recalls how he was trolling on Friendster—"Fagster," he calls it—when he and a friend figured out they'd both met the same guy.) Public nightlife options are almost nil beyond the Castro and SoMa. For lesbians, choices are even more limited—including the cliquey baby-dyke Mission bar the Lexington Club and a twice-a-month professional party at Mecca. "You want to hide but you can't," says Guillermo Perez, also 24, who works with Pyka at an ad agency. "You show up at Badlands in the Castro with a new guy, and a guy you dated is yelling ‘Whore!' from across the room."

One of the effects of this extreme insularity is the creation of a "gay ghetto," and not just in a geographic sense. Whereas in Manhattan, gays and straights often socialize together, bound not by sexuality but by interests (work, the arts), here, segregation is the norm. Many gay singles, whether by inclination or habit, frequent exclusively gay bars and parties where the only thing people may have in common is sexual orientation. "I could find a SoHo or East Village lounge where it was a little diverse," says Ian, a 29-year-old who arrived recently from Milan and New York. "The Castro's too gay. You feel like getting away from it."

"Good luck finding someplace else," adds Perez. "At the Clift there's, like, six gay guys, and they're all queens. The Mezzanine and the Endup"—two SoMa dance clubs that attract a druggie, shirts-off crowd—"are pretty sketchy." If you're too "ethnic," your problems multiply. "Guys don't want to strike up a rapport with someone who looks too different," says Ravi, 28, a Silicon Valley engineer who was born and raised in Bombay. In San Francisco's upscale gay scene—an alternative universe filled with dinner parties, Academy of Friends benefits, and trips to Puerto Vallarta—admission hinges on having the right skin color, the right degree, the right job, the right body. Remarked one man in his late 40s, intrigued and repulsed as he watched this clique out at a bar, "There go those evil cheerleaders."

An offshoot of this insularity is another common vice that contrasts with the Bay Area's oh-so-tolerant image: a penchant for putting people into boxes, whether by grad school degree or career choice, politics or tattoo count. "Dating has become like a job interview," says Judy Foley, a high-end matchmaker with a database full of San Franciscans who pony up $10,000 for her services. "It's not a salad bar where you can say yes to celery and no to corn. This is really small thinking." For those determined to find a lawyer-triathlete with real estate in a desirable neighborhood and a trust fund, the pool of eligible mates could fit comfortably in a Mini Cooper. And so people routinely complain that all the good ones are taken, when in truth, they've eliminated the mere mortals.

The boom exacerbated this phenomenon. People who leapfrogged professionally thought they could do the same romantically. Those who made millions often felt more entitled, applying a consumerist mentality to romance. "This is the land of custom-built mountain bikes," says Julian, 36. "People who come here want the best. What comes with that is an unwillingness to settle. So they stay single until they find an exact match."

Often, this translates to a self-defeating snobbery. Marie, the recruiter who finds men who come on to her cheesy, wanted to set up a friend of hers with a marketing manager from work, only to have her friend say, "I could never date a marketing manager."

Marie pressed on. "What if I told you he was independently wealthy?"

"Well, then he wouldn't be a marketing manager," her friend said coolly. When Marie later revealed that he was extremely wealthy, her friend changed her tune. "Too bad, you've lost your chance," Marie told her.

The Courtship: He Said, She Said
Many who do overcome the obstacles to meeting people discover they're perpetually stuck in going-nowhere relationships. Bay Area women kvetch about the Peter Pan syndrome—noncommittal men who refuse to grow up, settle down, and raise a family. Men, in turn, complain of status-conscious women so attuned to their biological clocks they hear nothing else.

Tim, the software guy, is typical of many men here. He spent his late 20s "holed up like a gnome" in a PhD program at Berkeley. Recently he's been clocking 70-hour weeks building his business. He and his "totally great" girlfriend of six months just broke up, because, among other reasons, he saw no reason to commit to anything less than a fairy-tale relationship. "I have a romantic notion about wanting to fall in love," Tim says. He knows his fantasy is a serious liability. "I may never get to know someone well enough to fall in love. But that's what could make me excited enough to get serious."

The Bay Area's stratospheric cost of living and relative workplace gender equality widens the social gulf between the sexes. Even in liberal S.F., men admit they have been socialized to be providers and the head of the household. They feel the need to be übersuccessful by the rest of the world's standards to even entertain the idea of maintaining a nice home here and providing for a wife and kids. So they become fixated on "making it" before mating. A still-weak economy has not helped matters. "Waves of singleness have consistently been connected to financial hardship," says Dr. Kathy Levdar, a Mill Valley couples therapist. "Delayed maturity has everything to do with financial pressures. In areas like the Bay Area, marriage delay is here to stay."

Once the instinct to defer coupling sets in, it feeds on itself. This is a central point of Ethan Watters's Urban Tribes, which recounts his own San Francisco life of delay. "Once the [single, tribal] lifestyle got going, it had its own momentum," says Watters, now a 39-year-old newlywed. "The fact that you live that way one year leads you to live life that way the next year. It became hard to jump off the bandwagon."

Meanwhile, this frontier town is constantly attracting smart, independent, hard-charging women who relate less to traditional male-female roles. Alas, this makes it harder for them to find love. To hear local women tell it, many men say that they want an equal. But give them what they claim to want, and many feel threatened or worry that they don't measure up.

"We're at a generational gender impasse," says Jane, 39, a writer. "There's total gender murkiness." Whether they like it or not, women who provide for themselves often leave men feeling they have no clear role in a relationship. Yet many of these women want to be asked out and generally treated like a lady. (According to a Match.com survey, men here are less likely to pick up the tab on the first date than men in any other city.) No one knows anymore who's supposed to do the asking, the paying, the kissing. There's an only-in-the-Bay clash of priorities at work, with women actually being less focused on finding a mate than men are. Only a third of women in our singles poll said having a great relationship is more important than having great friends. For men, the priority was reversed.

Marie, who attended school in Atlanta, has a theory about her career-oriented West Coast girlfriends: "They could use a play or two out of a southern woman's playbook." From her perspective, Bay Area women come across as "sharks." "They talk endlessly about work," says Marie, who downplays her own successes when she's on a date. "Southern women are smart and into their careers, but they know it's all about their man."

Marie's mind-set might seem regressive. But part of the gender role confusion traces to the fact that many women here don't think of themselves as different from the boys. The Bay Area, with its intense worship of the outdoors, attracts numerous "guy girls." Guys love them—they go toe-to-toe on gnarly mountain bike treks and pints of Sam Adams. But when it's time to get a girlfriend, the guys ask, "Where are all the girlie-girls?"

Then there's the baby thing. Pregnant pause. For a great number of single women who've turned the corner on 30, the baby urge is an elephant riding them piggyback into every room. Men sense this and go on high alert. "My friends and I have a name for the clock-ticking types: cougars," says Paul, a 34-year-old musician. "You can spot them a mile away. Like a dog smells fear." Past the age of 30, biological reality tips the dating balance of power to men, with women moving into a double bind. If they push too hard to settle down, they're seen as desperate; if they don't push hard enough, they risk aging out of their childbearing years. And when men do get around to marrying, they often pick women young enough to give them kids without automatic trips to a fertility doctor.
 
The Irony of the Bay Area is This:
It's so easy to be single that it's become hard to find love. Unlike in many parts of the country, there's little social pressure to settle into a serious relationship or marriage. Perpetual adolescence, or perpetual singlehood, is culturally sanctioned into the 40s and beyond. (For gays, the 20s and 30s are called a second adolescence, because their first one was in the closet.) And the singles crowd replenishes itself like halved worms sprout new heads. Perhaps that's why over half of singles in our poll called the Bay Area—despite the lack of love—a "good" or "great" place to be single. "I'm on my seventh circle of single friends," says Schwartz, the commercial producer.

In the same breath that Tricia, 31, an events planner, bemoans that her friends Karrie and Lisa have been through full-cycle relationships while she's remained single, she admits that she loves "dating" her girlfriends. Her friend Tonee chimes in: "You can't have sex with them, but it's stimulating enough." Moments later, a blonde across the rooms adds, "I have a vibrator." Karrie, seated next to her, responds, "I haven't had a vibrator since Seattle. I need one."

As children and teens, today's thirtysomethings experienced the nation's first divorce boom. Questioning marriage and proceeding with caution seem a sensible enough response, considering this is also the group that in the nineties perfected the "starter marriage"—an early trial marriage quickly ending in divorce. Each relationship let go in the 20s and 30s is viewed by many as a dodged bullet, unhappiness avoided down the line.

With this new safety in numbers, a singles pride is emerging. So is a less rigid dating culture, where marriage and relationships are an option, not an assumption. Those panicked in their 30s and 40s about growing old alone can take comfort in the fact that more than ever before, a sizable dating scene will likely be around well into their golden years. The term spinster already seems quaint.

Still, that doesn't mean the single life, however rich with friends and activities, isn't occasionally filled with moments of despair and bouts of "why not me" self-pity while blasting Diana Ross's "You Can't Hurry Love." For every failed date or romance, a friend's success story brings new hope. Or as with Olivia, the would-be fly fisherwoman, sparks new ways to meet a mate.

Even the most cynical, disconsolate single might be heartened to hear that consummate "tribesman" Ethan Watters recently married after spending two decades being a fulfilled single one moment and despondent and convinced marriage wasn't going to happen for him the next. Now that he's crossed over to the other side, he's like a mom who immediately forgets the pain of childbirth. "Did it take too long?" Watters asks. Without pause, he says smugly, "It took as long as it needed to take."