“I used to play a game with myself,” the sexologist is saying. (This sounds promising.) “I had a big basket under my desk, full of letters. I’d open each letter and try to guess where it was from. New York, San Francisco, Chicago? Were the cultures so different in different places that I could recognize them? Well, I couldn’t. There were swingers in Chicago, and there were people in San Francisco who didn’t know their ass from their elbow. I found no distinction, at least geographically. Or at least for the readers of alternative papers. So they were alternative people, I guess, to begin with.”The sexologist is Isadora Alman, whose syndicated advice column, “Ask Isadora,” once was a destination for pleasure-seekers everywhere, from the deliriously perverted to the merely perplexed. At its peak, in the other-than-progressive 1980s, her column ran in three dozen newspapers, including the national progressive beacon and alt-weekly colossus Village Voice. Alman presided over a benevolent sex-information empire—as radio host, author of books, leader of sex-information workshops, and ever-responsive taker of all questions you were afraid to ask.But “Ask Isadora” hasn’t been published for more than a decade, Alman’s radio work has since been reduced from host to occasional guest, and her books have nearly been squeezed off the crowded human-sexuality shelf. People still have questions, they always will, but no longer is Isadora the first person they think to ask. Having so successfully helped alternative people become mainstream, she rendered her own work unnecessary. Once a pioneer in her field, now Alman is out to pasture.It’s very pleasant as pastures go; on a recent morning I find her there, at her home office in Alameda, California, where she works as a marriage and family therapist. It’s in a quiet, sunny neighborhood full of flower-bedecked Victorians, and easily accessible through a purple back-porch door, just up a short driveway past the gleaming cherry-red Scion whose license plate reads “ISADOO.”“You have to come here in order to come here,” she tells me, innocent of all innuendo. “It is very much an island.” She means Alameda, where she moved from San Francisco in 2006, to be closer to her daughter and granddaughter. Alman has taken a seat and made hospitable gestures when, with an air of just-remembered concern, she stands again and closes the door to the next room. Ah, here we go. A secret alcove of carnal delights? No. It’s just to keep the cats out while we talk (the only freaky toys in plain view are theirs). We’re enclosed in a cozy hush of professional receptiveness.Wall décor here includes diplomas; small, tasteful engravings of coupled lovers; the official proclamation of “Ask Isadora Day” from former San Francisco supervisor Tom Ammiano; and the poster blow-up of one Alman-intensive cover of the Village Voice. “When I was going to NYU,” she remembers, “the pinnacle of success was sleeping with a Voice columnist.” The poster commemorates the moment she’d truly arrived. That moment seems as long ago as New York City seems far away.Make no mistake: Alman, now 74, seems like someone who’s had a gleam in her eye for her whole adult life. (The dust-jacket photo from her first book corroborates this.) She’s easy to talk to, in a way that surely has been titillating to suitors, reassuring to hotline or radio-show callers, and generally conducive to the decorum of a marriage therapist’s home office. Interviewing her here, it is tempting after a while to stop asking questions and start making confessions.Alman’s voice sounds like her: a blunt nonsense-averse New Yorker tempered by the legato New Age platitudes of Northern California. She is not haughty. She doesn’t take herself too seriously. Nor does she seem to think she’s particularly hilarious. It’s not hard to see how she can’t really compete in the current marketplace of pontificators. She lacks the grownups’-table skepticism of Dear Prudence, the out-and-proud attitude of Dan Savage, the au courant adventurousness of Tracy Clark-Flory. She’s a newspaper columnist, with all the glorious, bygone virtues—and marketplace deficiencies—of a newspaper.***“When I was a kid,” Alman once wrote, “we referred to used condoms washed ashore as ‘Hudson River cuddle fish.’ ” (She seems to savor the pun.) Born in New York City in 1940, Alman went to boarding school upstate at age 13. Not long thereafter, she says, “There was a friend of my father who felt it necessary to report to my father that his daughter was not a virgin. He felt it was his job to preserve the virginity of nice Jewish women. I hope my father told him to go fuck himself. It was that kind of humiliation that we were always subjected to. I was a product of my times.” For some context, consider that it wasn’t until 1952—the year before Alman went away to school—that the American Psychiatric Association finally allowed that the ailment formerly known as “hysteria” could in fact be the non-ailment known as female sexual arousal.At 16, Alman started college at Adelphi, on Long Island, in part because it was one of the few places to admit her at that young age. She began a non-exclusive “really hot sexual romance” with a classmate, who eventually dropped out. “He traveled with a carnival for a while. He was very theatrical. And so when he came into town we were lovers, and then he went away. That was most unconventional. At the time, good girls didn’t do any such thing. I felt no guilt. But there were a lot of questions I had and just no place to get an answer.” Contraception was available from the Margaret Sanger Clinic, at least, but only if she went in wearing a fake engagement ring.Alman was married for real, to another man, by 22. “I had a higher libido than my husband,” she recalls. “There was no such concept available in the whole gestalt of the society. Every joke was, ‘“Not tonight dear, I have a headache,” said the woman.’ Or he’s pleading with her and bribing her with a new fur coat or something. So where was I to go? I didn’t talk to my women friends because that would embarrass me and my husband. There was no frame of reference. I didn’t even know the word ‘libido.’”By 1979, Alman was divorced, living in San Francisco, working as a real estate agent, and feeling inclined toward community activism. By then possessed of a psychology degree from NYU, she took up volunteer training at San Francisco Sex Information, a nonprofit advice service, learning to answer anonymous hotline calls from anyone with any sexual questions. “But not for sexual entertainment,” she adds. “And there were a lot of those. People who just wanted to hear a woman’s voice say body parts, that sort of thing.” She learned to screen out the heavy breathers. Among fellow volunteers, she felt she’d found her tribe: people willing to talk frankly about sex, and to listen—willing to provide a public service they all personally wished they’d had. Noting the robustness of personal ads in the alternative press, and sensing a need, she pitched the San Francisco Bay Guardian on a column in the question-and-answer format.“The editor said, ‘Give me a few samples,’” Alman remembers. “I said, ‘Ask your editorial staff what they want to know, and I’ll write the first column.’ One of them was, basically, ‘I want to ask this guy out but I’m not sure if he’s gay. How do I find out?’ Right from the start it was both sexual and social.”The year was 1984. “This really redirected my life,” she says. With the guidance of California’s licensing agency, Alman cobbled together a customized master’s program: “My thesis was partially the book I wrote about San Francisco Sex Information, and partly about something I’m still interested in, which is the agreements that couples make regarding the sex outside the relationship. How does that happen? When does it happen, what are the parameters?” In addition to the column, and that first book, she also began a private counseling practice.Continue reading: Dr. Ruth and Dan SavageTo Alman, making sense of the sexual revolution through which she was living—from the “renaissance” afforded by reliable birth control, to the “truly hellish” peak of the AIDS epidemic, recollections of which now tinge that gleam in her eye with sorrow—seemed less like a job than a privilege. Readers kept telling her the column was their first stop in the paper, sometimes their only stop. Soon enough she was taking more of their questions, as the host of a local radio show.“My mom was not ‘famous’ until I was in college,” says Alman’s daughter, Jessica Lindsey, 49, an online collectibles retailer. “My friends all thought it was really cool. Of course, being a teenager, I was mortified. She is a good communicator. Sometimes it’s difficult to hear her opinions, especially more than once on the same topic—and particularly when I don’t agree with her—but she’s honest and is not afraid to speak her mind. She calls this being ‘assertive.’ I call it being annoying, often aggravating, and sometimes embarrassing.”During the “Ask Isadora” heyday, Alman’s own mother did volunteer work for various Jewish organizations, whose members tended to ply her with increasingly personal questions. Alman recalls: “She’d say, ‘I don’t know! My daughter didn’t learn this stuff from me!’ She wasn’t embarrassed, but she’d disown it a little. My daughter was the same way as a teenager.”As for her own religious life: “I am a godless Jew,” she says. “That was Freud’s description of himself. I say I’m a Jewish atheist. Because I acknowledge I’m culturally Jewish. I always have a Passover Seder because it’s a meal and a time to celebrate family and friends and freedom.” Alman’s calendar has been marked, meanwhile, for her granddaughter’s bat mitzvah next year. “She’s pushing the envelope; she found out you could do that at 12 in Israel, and she said, ‘I want to do that too, and get it over with.’ But I’m not observant. I am not generally in favor of organized religion, which I think does enormous damage in not accepting and acknowledging human sexuality. But I’m not ashamed of it, if people ask.”When calling for therapy appointments, people do ask. About her religious orientation, her marital orientation, her sexual orientation. “Sometimes it’s how they’ll make decision about whether to see me,” she says. “Once, I made an appointment with a woman who had social-skills issues, and right when I came to the door she said, ‘Oh, thank god you’re fat.’ So they’re looking for something.” If Alman’s not it, she’s glad to make a referral. Likewise, if the would-be client’s issue “is something I’d done a thousand times—gosh, another premature ejaculator, another woman who can’t find her clitoris: ‘OK, let me make a referral.’”*Scholars seem to agree that advice columns originated in London in the 1690s, with the Athenian Mercury and its sister paper The Ladies Mercury—the latter of which ran a column called “Love, etc.,” neatly forecasting both the basic premise and the raw material of many of its descendants. Alman’s most direct predecessor was “Dr. Ruth” Westheimer, the oft-parodied German psychologist and Holocaust survivor best known for mainstream-friendly sex talk on her own radio show, which debuted in 1980. “She was a pioneer,” Alman says, “and could be because she was so funny-looking and because she sounded so funny. I was an attractive, youngish woman when I started. Which could be threatening. So I was taken in a different way.”Alman and Westheimer took different approaches to the material. Alman recalls sitting on a panel with Westheimer in San Francisco once, where audience questions included one from a man who had trouble putting on a condom. “And she says, ‘Vell, maybe your vife vill help you put it on.’ And I thought: ‘Where is she living?’ Not here, obviously. I mean, the assumption, first, that he’s married, and second, that he’s straight. So that was the difference between me and Dr. Ruth.”Differences with her successor were decidedly sharper. Dan Savage’s “Savage Love” began, in 1991, in mostly the same way that “Ask Isadora” had—with the first column’s letters generated in-house by alt-weekly colleagues, spurring a stampede of many more from readers. One obvious difference was of tone, readily apparent in how the Savage columns, at first, were addressed: “Hey, faggot.” It began as a palpably pissed-off lark, turning the tables on homophobic contempt.The advice itself sometimes was so routinely brusque as to warrant abbreviation; thus, “Dump The Mother-Fucker Already,” became “DTMFA.” At the time, Alman described Savage as the Howard Stern of sex advice, and Savage took it as a compliment. The year 1991 was also the year of Thelma & Louise, of Clarence Thomas and Anita Hill. Obviously not all of America’s sex questions had been satisfactorily answered, and the conversation was only getting more heated.Within a decade, it had all but boiled over, and “Savage Love” had essentially wiped “Ask Isadora” off the alt-weekly map. Readers had new questions, and were ready for a change. “How many times can we read about someone with a non-vanilla interest wondering if they’re ‘normal’?” groused one Baltimore reader in a 2001 letter applauding the City Paper there for replacing Alman with Savage. He concluded: “Don’t let the door hit your tired ass on the way out, Isadora!”Continue reading: Happily ever after?Once in a while, Savage himself would let fly the occasional snipe—here supplying a horny underage virgin with Alman’s contact information, there asking “what ever happened to” her, very obviously not really caring. In the appendix of a book collecting his own columns, under the mildly immodest subtitle “Straight Answers from America’s Most Popular Sex Columnist,” he listed her, along with the American Family Association, Focus on the Family, and Dr. Laura Schlessinger, as a reliable source of bad advice. Today, when contacted to reminisce about their rivalry, Savage chimes in only very briefly, by text: “Not much to say. She tried to smother me in the crib, failed.”Alman doesn’t want to talk about it either, but her daughter ventures a comment. “I think she was not controversial enough for changing times, perhaps too accepting and not judgmental enough,” Lindsey says. “Dan Savage was controversial, shocking, and the opposite of not-judgmental. I think they were looking for someone younger (and gay) who could create drama.”By the early 2000s, Alman had published three more books, collecting and elaborating on her columns, but also had started losing newspapers. Her last column ran in the Guardian, her original newspaper, in December 2001. Of course, it is the nature of all newspaper columns not to last forever. Especially in an era when newspapers themselves face extinction. To properly reflect on how the world has changed in 30 years is to note that “Ask Isadora” came into it at the same time as the Apple Macintosh, and Mark Zuckerberg.“Early on,” Alman says, “I saw a man whose life was really tortured by the fact that he was a cross-dresser. He felt disgusting and disgusted with himself. He was a loner, he was an alcoholic. And when I normalized that for him—let him know that other people did it, that the world wouldn’t end—it was like the sun came out. Ten years later I would tell a client to look on the Internet. And you will find a group of like-minded people, with whom you can discuss where to buy large-size high heels, or whatever it is.”Not that the Internet has done much to improve human social skills. “The stuff that’s in my earliest columns is the same stuff I’m seeing now,” Alman says. “‘How do I find a partner?’ ‘How do I keep the relationship alive and healthy?’ ‘What do I say in certain sticky wickets?’ Across the board. Whether they’re gay or straight or other, young or old, single or not, or questing, the issues are the same and the questions are the same.”In addition to her therapy practice, she’s still writing now and then, most recently for the blog of Psychology Today. “Sometimes I think it would be nice to have my column reinstated somewhere, but I don’t have the energy or the cojones to pursue that,” Alman says. “And I understand that the way it happened originally, it all just fell in my lap. I still get people saying, ‘I always read you in the Guardian’ even though I haven’t been in it for years. But they remember.”It is strange to think there could ever be such a thing as an obsolete sexologist. It’s not like Alman ever would have cause to say, “My work here is done,” and turn her attention at last to some other subject. “Becoming intimate is a step-by-step series of risk-takings,” she once wrote, and clearly every generation must take those risks anew.“I learn over and over again that we’re all human,” Alman says. “That our society makes us feel bad about ourselves in some way. Because that’s what sells products. No matter who we are, apparently we are not okay. Just on the surface of things. Our body as it is needs to be plucked or shined or shaved or reduced or uplifted.” Presumably that’s still as true in New York and Chicago as it is in San Francisco.So would she care to make any predictions about where the species is headed? “Marriage, the nature of coupling, will change,” she says. “We already have serial marriage condoned, although we don’t call it that. I think as there’s been this arc of change, there will be an acceptance of contractual marriage—say, two years with an option to renew. An acceptance of all kinds of alternative ways of having your emotional and economic means met.”Alman herself already has enjoyed a somewhat unorthodox happily-ever-after. That lover she’d had in college, who’d gone away with the carnival? “We have reunited after 50 years,” she says, and now he’s a novelist, who lives with her in Alameda. “What I really hope for may sound a little boring, but not to me: I just want more time for us to be together.”***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.Jonathan Kiefer is a writer in San Francisco. Follow him on Twitter @kieferama.