A slender, leggy lawyer who is long on looks, poise, and confidence, 33-year-old Hilary Ware was getting married, and—a midwesterner to the core—she was going for the whole something borrowed, something blue affair. She chose a strapless fitted bodice in silver-on-white shantung silk, which she could more than pull off. (Her shoes: Gucci stilettos.) Meanwhile, her partner, Wendy Kosanovich, 41, an attractive combination of demure southerner and quick-witted litigator, picked a flowy platinum skirt and camisole with matching silver Manolo Blahnik sandals peeking out beneath. The ceremony, before 125 of their closest friends and family, would take place in San Francisco's high-ceilinged, Craftsman-style First Unitarian Universalist Church; four flower children in Mary Janes and little navy suits would carry tiny wicker baskets filled with white rose petals.

Then, several weeks before the big day, an old friend called. After chatting for a while, the woman told Ware she had a question. Well, it was actually her husband's question, she added sheepishly, and stemmed purely from concern for their six-year-old daughter, Alexandra, whom they planned to bring to the wedding. "So, are you two going to kiss at the end?"

As Ware recounts the story ten months later, over cappuccinos at a downtown café near her Heller Ehrman office, she tosses her head in unfiltered annoyance. At the time, she had answered her friend politely, not revealing her irritation. (The upshot of her tactful answer: Hell yes.) She and Kosanovich went on to have the fairy-tale wedding they had envisioned, and the friend and her husband were all smiles. But now, for a moment, Ware vents. "Ugh, that made me cranky. I mean, come on, folks! Give me a fucking break." To Ware, this was a classic "clueless-straight-people moment," borrowing the term a sharp-tongued strategy consultant, Cynthia Dai, 37, had used just days before.

Don't be alarmed; Ware and Dai and their friends aren't curling their lip at all straight people here. Neither are the many other thirtysomething and fortysomething lesbians now mingling in ever higher, ever straighter echelons of Bay Area life. It's just that in the aftermath of a season of mainstream affirmations of lesbian romance (2,266 teary-eyed lesbian couples making their love official in the grand rotunda of City Hall), lesbian chic (the success of Showtime's L Word), lesbian authority (several of Gavin Newsom's top aides are gay women), and lesbian cachet (suddenly the gay card is Willy Wonka's golden ticket into many of the city's primo, diversity-starved private schools), upwardly mobile gay women have something to say about the heteros they deal with as they go to work in their wood-paneled offices and drop off their kids at their superselective preschools. And it's this: You sure know how to take the glamour out of the lesbian moment.

"It's a total pain in the ass," says Kaila Compton, a 40-year-old medical school graduate and Eureka Valley mom who's also

been noticing how often—despite the Bay Area's worldwide reputation as the home of Free to Be You and Me—its straight elite still trips up on (or tiptoes around) the lesbian thing. As Ware puts it, "You give a pass to the Walgreens guy who asks about your husband when you pick up a prescription. But the people who claim to be so progressive—really, they have to dig a little deeper."

While power lesbians in the city's million dollar neighborhoods don't seem to be losing sleep over their daily dealings with unenlightened straight people, they do get crabby in a hurry when asked directly about the problem. Compton and others have perfected the eye roll in response to the many minor incidents—a casual friend who muses, "Maybe he's gay," as your four-year-old son pirouettes across the playground; birth certificates that still read "mother" and "father"; the overheated quips from the boys at the bar if you dare to nuzzle in public (even in a sophisticated spot like Bacar) that can give lesbian life here a gnat-in-the-ear quality. No matter how much you hop around and shake your head, the annoying buzz persists.

For straight people who aren't themselves guilty of such faux pas, it's hard to believe these moments happen often. But lesbians describe a parallel universe of establishment types and their awkward ways that kill some of the fun of being a lesbian here. Ware, for instance, gushes about what an amazing firm Heller Ehrman is to work for and how it came to be such a haven for whip-smart, Ivy League-groomed lesbian lawyers. But in the next breath she describes her friend Matthew*, with whom she gets together occasionally for coffee to catch up. Inevitably, just as they're sitting down, the "terminally earnest, liberal East Coast-bred" hetero attorney tosses out some obscure lesbian factoid or issue, most recently a news story about a gay couple in Connecticut suing for joint health benefits. "I swear he Googles gay topics before we get together," says Ware. "I finally said to him, ‘You know, I'm actually quite fluent in hetero topics like, What did you do over the weekend?'" Kosanovich, who was one of the first "out" lesbians at Orrick, Herrington & Sutcliffe, where she worked until recently, has also heard her share of innocent bloopers. "‘Does a lesbian like her steak rare or well done?'" she parrots only slightly facetiously. Her well-worn comeback to assumption-laden comments: "We don't all have one brain, you know."

Even this year's gay-marriage boom at City Hall had its aspect of "You just don't get it," as straights went gaga over weddings of friends and acquaintances, somehow forgetting that many of these same couples had already gotten married, some quite elaborately.

The best explanation of the gap may be that upwardly mobile straights and gays alike have a tendency to self-segregate, which leaves even the most politically correct

straight people unable to learn how not to look clueless. Thinking back over their busy weekend, straight professionals interviewed for this story admitted it was anything but a rainbow parade. Lauren Schwartz, 38, is a South of Market TV-ad producer with a clique of mirror-image straight friends raised on the East Coast, educated at elite colleges, and armed with MBAs. "One is at a toy company, another is a career coach—that's what we call diversity," Schwartz says. "It's on a seriously narrow band." Likewise, Crystal Brown, 32, says her existence as a Marina mom grouped with other Marina moms in the great salad bowl of San Francisco calls to mind lunch-table divisions from her days as a student at Berkeley High. "A school doesn't get any more diverse, and still, our tables didn't mix," says Brown. Clique living leaves many Bay Area straights, while "hip" in theory, less at ease than they might wish.

It's difficult to say whether gay men in the city are any more socially integrated (or any less irritated by the slights). Research indicates that gay men suffer more stigma in the straight world than lesbians, yet men in general have more economic power and access to connections, so maybe it's a wash. But either way, what's most striking at this moment is how fast-track lesbians are ensconcing themselves, too, finally no different from the country-club set in Ross. Lawyer Kelly Dermody, 36, whose gang of 16 closest friends, while racially and ethnically diverse, are all lesbians, says it comes down to comfort. "My life is so crazy. Working with clients, I'm the only lesbian most of the time, and almost always the only woman. I want my free time to be totally easy and relaxing." Amy Errett, 46, left a long career in buttoned-down financial district jobs to run Olivia, a gay travel agency. "At some point, you just say, ‘Enough.'" Clicking through her Palm, she is struck: "My God, my world has gotten small."

This oil-and-water existence leaves many straights floundering like characters in an awkward scene from a Jane Austen novel; apparently some combination of performance anxiety and just plain lack of experience gives them two left feet when confronted with a lesbian. "Conversation gets a little less flowy, put it that way," says Julie*, 35, a gay woman and product developer at a local financial firm. "I found myself doing a high-wire act," says one straight San Francisco attorney who inadvertently offended a gay colleague by mentioning facts about her friend's personal life to a client. "I had no idea I wasn't supposed to say anything."

Some straight-lesbian clashes aren't benign. In Portola Valley, prominent gynecologic oncologist Kate O'Hanlan and her partner, Léoni Walker, recall having an awful time getting a hot tub approved by their neighborhood association. After several permit resubmissions, their architect tipped them off to the holdup: homophobia, pure and simple.

"What did they think we were going to do—have orgies?" asks an incredulous O'Hanlan, laughing. When the architect cried foul, lo and behold, the hot tub was cleared. O'Hanlan's take on being lesbian in Portola Valley: "It's basically no better than Tulsa." She's being flip, but you can tell she's about ready to flip off the next straight person who disses her.

To Tomas Almaguer, dean of the Ethnic Studies College at San Francisco State, it's not surprising that local lesbians are getting increasingly bugged about the slights, even if they mostly keep their complaints private; it's supposed to be their heyday. "With privilege comes a sense of entitlement that makes the issue more pronounced," he says. It's the same situation faced by any outsider who finally succeeds inside the mainstream culture. "Whether you are gay, an immigrant, fat, African American, there's burnout," adds Esther Rothblum, a visiting professor of psychology at UCSF's Lesbian Health Research Center. "You constantly need to explain yourself. Your words become those of an entire group."

To lesbians like political leader Kate Kendell, the Bay Area is still utterly "hetero normative." That's why so many gay women, especially those in professions that remain hidebound the world over (read: finance), are still in the closet at work. While Janet* and Sara*, who've been together since attending Wellesley, have a son and a Potrero Hill home together, no one at the white-shoe investment bank where Janet works knows about Sara. (Janet told everyone at work she'd adopted the baby Sara had just given birth to.) The rationale for the elaborate, and increasingly painful, ruse: She wants to make managing director and is certain that many of the 50 bankers in her San Francisco office would feel uncomfortable shooting the breeze with her during five-hour flights to New York if she came out.

For those who long ago took the leap, the surprise is having to come out again—and again and again. Each time someone asks where your husband is or a client invites you and your boyfriend out to celebrate the big deal, you have to either explain your situation or duck and run. How does that feel? Several women summed it up the same way: "It's exhausting."

When kids come along, of course, any chance of passing in the straight world disappears into the bottomless diaper genie. "It's hard to hide when your kid is standing there next to both of you, screaming ‘Mama! Mommy!'" says 40-year-old Jane*, a writer, whose daughter is now two. Some fast-track lesbians say they experienced being outed by their kids as a cold plunge. It doesn't help that the other parents at the tony preschools and elementary schools where they send their children are a little less progressive than some enthusiastically composting parents might like to believe.

Take this scene at the Marin school to which every organic-produce-purchasing mom would like to send

her kid. At last year's back-to-school night, a group of parents huddled in one corner of the classroom. One sporty mom made her way over to Molly Dwyer, 45, the no-fluff chief deputy clerk at the U.S. Court of Appeals, whose daughter was one of two first-grade-class kids (out of about 20) with gay parents. "They voted me the one to ask," blurted out the mom, blushing. "What do we call Susan?" To which Dwyer bluntly replied, "I call her Susan." Dwyer was a bit shocked to be reminded that affluent Marinites often hadn't dealt with gay families before. Still, she says she admired the woman for asking.

When these upscale schools are for girls only, the presence of lesbians—parents, teachers, donors—becomes an even hotter potato. In one incident at a plaid-skirt private school on the Peninsula, a donation made by the Lesbian Equity Foundation of Silicon Valley was politely declined. The reason: to keep the foundation's telltale name off a plaque slated to hang at the school's new pool. The school's headmistress didn't even try to cover up her motive for refusing the check. "She said, ‘If you'd be willing to write a check from your own personal account, we'd be happy to have it,'" recounts former E-Trade president Kathy Levinson, one of the area's most prominent lesbians, who sent the gift from the foundation she started with her bull market bundle. When Levinson saw the sign, which has around 200 names on it, she couldn't believe it. "You'd have needed a magnifying glass to even see the name," she says.

In San Francisco, another school stopped celebrating National Coming Out Day after a group of parents vehemently protested. According to a prominent academic and mom who attended the emergency meeting called to calm parents, "The homophobia expressed that night was so intense. The gay teachers were totally freaked out. They're still reeling from it several years later."

Robin*, 43, has a unique perspective on lesbian life here. She has lived it, and now, married to a man, resides in Marin with her husband and teenage daughter. She is one of many "hasbians" living around the Bay, women who used to be in a lesbian relationship and are now married to men. There is no evidence of a widespread conversion, but hasbians aren't hard to find, either. While there is little commonality in their stories, there is a powerful (albeit somewhat guilty) universal sigh: Life is a hell of a lot easier now.

Robin, who is generally tight-lipped about her past, has done plenty of reflecting. "I still think about it a lot. Why is being gay such a big deal? Why is it such a big debate on all levels—in political and social circles? It was huge for me. Why is that?" Yet she recognizes her own similar instinct: "When I meet someone, I still wonder, Is she gay?"

Turns out people need to put each other in a box even in the most liberal neighborhoods on Earth. Layer in the American default position that sex

is between a man and a woman, and we're facing a cultural gap that won't go away—here or anyplace else—anytime soon.