The Billionaires’ Vagina Club

Sally Greenwald likes to say that she is the happiest gynecologist in America. She is certainly sought after, having attracted a following of high-powered Silicon Valley women of a certain age with her motto, “Sexual health is health.” Recently, Greenwald was the guest of honor at a small luncheon hosted by one of her patients, the tech entrepreneur and philanthropist Gisel Kordestani, in Atherton, California, one of the wealthiest towns in the country. The event took place in the stately, pillared home Kordestani shares with her husband, Omid, the former chairman of Twitter.

Kordestani, who has long, light-brown hair and was wearing platform Prada sneakers, apologized that her co-host, a fellow Greenwald patient named Nicole Lacob, who runs the philanthropic foundation of the Golden State Warriors (her husband, Joe, is the majority owner), wasn’t able to come at the last minute. She had flown to Paris to attend the début runway show of Matthieu Blazy, the new designer for Chanel.

The other women in the room murmured in understanding. Ranging in age from late thirties to mid-fifties, they were accomplished, confident—the kind of women for whom “Fake it till you make it” had long ago morphed into “Make it better and better.” When I moved to Silicon Valley from New York, fifteen years ago, I was astonished by the widespread conviction that everything—even one’s body, aging and mortality notwithstanding—must and will improve, like each new iteration of iPhone.

Greenwald, who is forty and has a spirited demeanor, perched on the edge of a chair, ready to field questions. “Use my brain!” she told the women, her high blond ponytail bouncing. “Meander me wherever you want to go.” The doctor, who grew up nearby, in Los Altos, fit in easily with the group. Her sparkling Jimmy Choo flats peeked out from under a long, rainbow-striped dress, and her language immediately signalled that she shares Silicon Valley’s obsession with optimization and innovation—“perseveration on perfection,” she calls it, a determination to bring the entrepreneurial mind-set into every aspect of one’s life. The women at the lunch were not content to enjoy good health; they were looking for a way to level up. (The latest term for this is “healthmaxxing.”)

One difference between Greenwald and the dozens of biohacking doctors who treat the area’s billionaire tech bros is that she wants to achieve this goal, in part, through orgasms. (Lube, she likes to say, is as essential to one’s routine as sunscreen.) Rather than concentrate on increasing life span, she focusses on what she calls a woman’s “sexspan.” Her concierge gynecology practice—which is situated on the Stanford campus, where she is an assistant clinical professor—views women’s sexual health as a way to well-being and, ultimately, to longevity. She makes the case that “bro science” culture typically relies on research that excludes data about women. (Rock-star longevity doctors like Peter Attia and Andrew Huberman come to mind.) Part of Greenwald’s approach involves using cutting-edge hormone therapy, among other interventions, in unconventional ways. She also counsels women to have more and better sex, devising stratagems like Fuck-It February, a prescription to have sex as often as possible in the year’s shortest month. New patients pay tens of thousands of dollars a year to join her practice, if they manage to get off of a wait list. Some have sought Greenwald out after hearing her speak at private gatherings hosted by fans like Priscilla Chan Zuckerberg. Last fall, after a fierce auction, Greenwald received a seven-figure book advance from HarperCollins. Sheryl Sandberg is writing a blurb.

Sandberg described Greenwald to me as “brilliant, energetic, passionate,” adding, “She’s unafraid to broach topics in ways that other people, I think, have been afraid to do.” In the past few years, as her wait list blew up, Greenwald started jokingly referring to her practice as the B.V.C.—the Billionaires’ Vagina Club. Some patients found the name amusing, but the billionairesses apparently did not. Greenwald stopped using it.

Seated in Kordestani’s grand living room, the lunch guests told Greenwald about their frustration with their primary-care doctors, whom they viewed as old-fashioned disease chasers. “I like biohacking,” Kordestani said, but complained that her doctors were dismissive. The women wanted physicians who were disease preventers, and doctors who were attentive to the difficulties wrought by menopause, which have been increasingly found to leave women vulnerable to other ailments. (I first met Kordestani at a book group that was reading “All Fours,” Miranda July’s 2024 novel about a woman teetering on the estrogen cliff of perimenopause, ditching her husband and child in the process. The book-club members roundly disliked it, indignant that the character was being driven mad by perimenopause, as if hormone-replacement therapy didn’t exist. Did July just have a bad gynecologist?)

Outside Kordestani’s glass doors, a gigantic inflatable flamingo moved back and forth in an infinity pool. Inside, one young woman asked Greenwald, “How do I know when I’m in perimenopause?”

“My goal is that my patients never know,” Greenwald answered, segueing to her enthusiasm for hormones. She told the group that she had several Olympic athletes as patients. As soon as their schedules for the 2024 Paris Games were released, she used an ovulation medication to synch their cycles so that they would compete on days nine through fourteen—the time when estrogen peaks and women are suffused with energy. In perimenopause, she said, the pattern shifts: fluctuating hormones can cause days and days of angsty P.M.S., followed by spikes of anxiety. “Fortysomething women can get quite a reputation,” she noted. “These are badass women like yourselves, who run companies, run households with a lot of children, have M.B.A. careers and whatnot, and all of a sudden they’re freaking out at everyone.

“I’m super excited about using hormones, maybe forever,” Greenwald went on. “I will humbly bow my head when the data come out to prove the opposite, but I really think we’re onto something.”

When she is talking about scientific innovations, Greenwald warns her listeners that she is prone to “go super dorky.” Although the women she treats are data-driven, they are impatient—unwilling to wait a decade for randomized controlled trials, then years more for prescribing habits to change and insurance companies to catch up. She makes treatment recommendations based on a combination of what she calls “biological plausibility”—a theory of why something would work—and new data. “There’s a lot of cool new meds on the market that I’m super excited about that few doctors are using,” she said. “But I am!

“I want to be very clear about when I’m speaking as a U.C.S.F.-trained physician with lots of randomized control trials behind what I’m saying, versus when I’ve entered the ‘woo-woo’ world of concierge medicine and I’m going into anecdotal evidence and observational studies,” she said, fluttering her hands. “You guys are a very smart room here.”

Cartoon by John O’Brien

A woman mentioned that some of her friends were paying for their young daughters to freeze their eggs, as a graduation present.

“Super interesting! That’s a great idea!” Greenwald said. “This is my favorite example of population-based health versus concierge health.” Research shows that most women who freeze their eggs before the age of thirty-seven don’t end up using them. “But suppose we don’t care what the cost is?” Greenwald asked. The calculus becomes simpler. Everyone knows twenty-one-year-old eggs are better.

Cori Bates, a trustee of the Asian Art Museum who is married to the C.E.O. of the software company Genesys, leaned forward. Bates was wearing a scarlet dress and kitten-heeled flip-flops, and she spoke up to say that, after learning that she was at a high risk for ovarian cancer, she funded a study to assess whether risk for the disease can be reduced by removing one’s fallopian tubes.

Greenwald praised the study, and Bates took the opportunity to ask if the doctor would take her as a patient. Greenwald beamed: “I’m so, so flattered. I would love to. But I’m completely full.” She promised to try to find room for Bates in the future.

Someone asked Greenwald how she felt about hormone-monitoring apps, and she answered that the technology is not there yet and that the apps on the market are unreliable. She addressed her audience: “Please, make a good app for teen-age girls—and for perimenopause and menopause.” The women smiled, then everyone filed into the dining room. Greenwald left before dessert so that she could be home in time to meet three of her four sons at their bus stop.

I met Greenwald three years ago, when she was consulting once a week for the primary-care practice where I was a patient. She strode into the room looking like a television doctor in a chic blue-print dress and flats. (She favors prints, she told me, because they disguise splashes of bodily fluid.) By then, I was skeptical of gynecologists. I had consulted three about insomnia, brain fog, and vaginal atrophy, which made sex painful and left me with recurrent infections, only to be told that the ill effects of menopause are just a “natural stage of life” which could not be medicated away. Then the doctors would bustle out to see their more appealing patients—the cheerily pregnant ones, whose deliveries constituted the bulk of their income and whose babies would be added to the collage of photos decorating their office walls. Greenwald told me that, even though I had been prescribed some hormones, she felt that I had been undertreated, because doctors often use hormones too sparingly; she prescribed five different forms of hormones to me, and my old life resumed.

I texted my middle-aged friends the details of my prescriptions: estrogen patch (estradiol, 0.075 mg.), vaginal ring (Estring, 7.5 mg.), estrogen cream (estradiol, 0.01 per cent), oral progesterone (Prometrium, 100 mg.), compounded testosterone cream (start at 1 mg., then move to 2 mg.—up to 10 mg.). They pressed their own doctors, who hedged or shrugged but eventually wrote the prescriptions for them. When my friends found relief, they were thrilled—and infuriated. Why were they getting this information from me and not their doctors?

For many women, menopause marks a retirement from active sexuality. They may still have sex, in the way a retired athlete may still throw a ball around the back yard, but the drive is gone. Greenwald wants to get these women back into the game, because research shows that a healthy sex life brings a variety of benefits that can contribute to longevity. Her methods combine treatments with sex tips. “How many sexually active years do you want to have?” she asks patients. “If having orgasms in your eighties is on your bucket list, you have to work at it.” A faltering sex life can also put a marriage at risk, and statistics suggest that people who stay partnered live longer. In the 2024 General Social Survey, nearly two-thirds of married adults reported having sex less than once a week, and twenty-eight per cent answered that they had sex rarely or not at all.

Women’s sexual health has been under-researched, and in recent years federal research money into women’s health issues has been slashed. But menopause is finally having a moment. Last November, the F.D.A. removed the “black box” warning (the agency’s strictest safety alert) against H.R.T., and earlier this month Melinda French Gates announced a two-hundred-million-dollar menopause- research initiative. A 2024 meta-analysis published by the Bulletin of the World Health Organization looked at sixty-three studies and found strong correlations among over-all health, well-being, and sexual activity. A study from the same year in the Journal of Psychosexual Health analyzed government data and found that women who had low sexual frequency had a forty-six per cent higher mortality risk. It seems obvious that healthier people might be more sexually active, but Greenwald believes that the association is bidirectional: that good sex leads to good health. Orgasms improve mental health, suppressing stress hormones like cortisol and releasing dopamine and oxytocin; women with robust sex lives report less depression and anxiety. Studies show that orgasms also relieve menstrual pain, lower blood pressure, enhance circulation, correlate with better cardiac functioning, and burn calories equivalent to thirty minutes of brisk walking. Orgasms also activate parasympathetic pathways that promote deeper and longer sleep. There are measurable health benefits to orgasms through masturbation, but those benefits compound in partnered sex, which supports satisfying long-term relationships, which in turn correlate with better health and longevity.

“The argument is not: sex equals longevity,” Greenwald said. “It is: sex equals sleep, stress reduction, cardiovascular engagement, relational fulfillment, and pelvic-floor health, and each of those equals health.” She likes to note, however, that sixty years after the so-called sexual revolution, the sex lives of straight women are hardly thriving. Whereas straight men climax in almost all sexual encounters, heterosexual women in relationships fail to climax a third of the time. The widespread assumption has always been that the female orgasm is innately tricky, but data show that lesbians climax almost as often as men do.

A number of Greenwald’s patients told me that they’d never had a gynecologist who thought of sexual satisfaction as a medical issue. But she considers sex coaching to be a part of her job, just as an internist might advise a patient with high blood pressure to get more exercise.

There is a girlfriendly “pass it on” quality to the way word has spread about Greenwald’s treatments, which include birth-control pills—such as Nextstellis and Natazia—that contain a new natural form of estrogen, not the synthetic formulation in most pills; compounded testosterone cream for a “kick-ass sex-drive booster”; magnesium glycinate for sleep; temperature-controlled mattresses; her preferred vibrator for postmenopausal women (a long-handled model with seventy-to-a-hundred-and-fifty-hertz frequencies); and silicone-based lube. Greenwald has been known to draw diagrams for patients, showing them how to find their G-spot.

“Experts describe sex in biopsychosocial terms,” Greenwald told me. “I tell my patients, ‘Think bio.’ ”

Nicole Lacob, the wife of the Warriors owner, started seeing Greenwald over a year ago, when she was fifty-six—just in time, in terms of starting hormone-replacement therapy. (For women more than ten years into menopause, H.R.T. can boost mood, libido, and bone health, but it also presents cardiovascular risks, among others.) “I wish I’d had her when I was forty-five,” Lacob said. At the time, she recalled, she was too depressed to even shower: “I was crying over things all the time, and I had no idea that it was even perimenopause.” Lacob was seated with her legs tucked underneath her on a fluffy couch in the living room of her Mediterranean-style estate. She has a cascade of dark hair, and wore platform Uggs. (At Warriors games, she is often seen on camera dancing in glittery thigh-high boots beside her husband.) “I think I would probably even look ten years younger now if I had had her then,” she said.

Lacob had always liked the house warm—she used to tease her husband that, if he ever wanted to see her naked, he’d need to keep the heat cranked up. Suddenly, she was always too hot and couldn’t sleep because of night sweats. She’d had breast cancer in her thirties and, consequently, had been warned away from H.R.T., which has been thought to be unsafe for cancer patients. But Greenwald explained that there is only a modest increased risk of recurrence. (This is a controversial position and one that many oncologists oppose, in the belief that data are still emerging and that even a modest risk is not worth taking.) She prescribed an estrogen patch to alleviate the night sweats and an estrogen ring, which is placed inside the vagina and releases local doses of the hormone. “Then Sally asked me questions that I never thought to ask myself, um, regarding desire,” Lacob said.

“I was shell-shocked the first time,” Nathalie Dompé, the Italian-born head of a pharmaceutical business and the wife of the tech entrepreneur Chamath Palihapitiya, told me, laughing at the memory of just how graphic Greenwald’s questions can be. “The best part is when I go home and repeat all my new learnings to my husband, who looks at me, shocked.” She appreciated the way Greenwald “puts it on the radar and says, ‘This is part of how you take care of your life.’ ”

I sat in on one of Greenwald’s appointments, with a patient I’ll call Kristen, the wife of a celebrity. She had been suffering from depression and mood swings triggered by the hormonal fluctuations of perimenopause. She confessed that she sometimes found “the mental load of being a mom”—she has teen-agers—almost unbearable. Greenwald had been treating her for a few years, and they were, Greenwald said, “making progress as a doctor-patient couple.” She had evened out Kristen’s cycles with birth-control pills, and Kristen’s mood and energy had improved. She’d even picked up some old interests again, like exercise and crafting. But not sex.

Greenwald hears this story again and again. After they became mothers, her patients tell her, their focus transferred from their romantic lives to their children. Kristen’s husband’s life was full of glamour and limelight, whereas her life was all behind the scenes. He was taking testosterone to keep up his physique; his libido was stronger than ever. But satisfying him felt like one more chore.

Seeing Kristen’s shoulders slump, Greenwald smiled. “When you’re, like, ‘Help a sister out with her sex life,’ know that you’re in good company.” Greenwald said. “Just imagine my very sexy life with my four kids and three jobs!”

Kristen said that when she accompanies her husband on work trips without the kids, she feels pressure to be a sex goddess. “I can tell, after the first night, that he’s thinking, That was fun, but no one was swinging from the chandelier,” she said. She missed having “the desire for more spontaneous, fun, crazy sex.” When she was younger, alcohol helped, but these days drinking made her fall asleep more than it loosened her up.“I still like my guy, and I think he’s cute,” she said shyly. “And I want him to only be with me.” But she said that, when he asks if she wants to have sex, it seems that he’s not really asking about her desires. She feels like saying, “No, I don’t. And now you’re annoyed because that was the least sexy answer I could give. But your question was manipulative.”

Greenwald jumped in, completing Kristen’s thought: “Does it look like I want to have sex? I’m sitting here ordering groceries. What about me ordering groceries says, ‘I want to have sex’?”

Then Greenwald made a characteristic pivot. In fact, she always tells patients, any time is a good time to have a certain kind of sex—what she calls “efficient sex.” She believes that the best way to improve sex is to drop the romantic notion that it requires a special frame of mind. Better to have a quickie, even if you’re reluctant, because an orgasm can improve your mood, and ultimately your health and your relationship.

“I’m not going to talk about chandelier sex,” Greenwald added. “That’s a good hobby, and, if you have that, rock on.” She continued, “We’re going to stick to super-heteronormative, vanilla, white-picket-fence sex that has data behind it.” She had suggestions on how Kristen could “curate” her own arousal. Spontaneous desire, she said, disappears in eighty-five per cent of women in partnerships after about eighteen months. But women retain responsive desire—which comes from being stimulated, or from stimulating themselves. “If I were to write a porn for women in our forties, fifties, and sixties, it would start with a vibrator and some lube.” Think of it like exercise, she said: you never want to do it, but, once the trainer arrives and you begin, you get in the mood.

Kristen nodded: “Before my trainer gets there, I’m, like, Fuck you!”

Greenwald went on, “But why do you show up? You’re thinking, Once I start to exercise, I know how good I’ll feel afterward.” She counselled Kristen to hop into bed with a vibrator, then, after warming up, text her husband and ask him to come to the bedroom for a few minutes.

“I know that you’re, like, That doesn’t feel sexy,” Greenwald said. “But it’s showing up at the party, even if you don’t think you want to go, and then having a good time.” She continued, “I know it’s awkward in the MeToo era.” She realizes that her message—“Just try it, even though you don’t want to”—can sound retrograde, misconstrued as an update on “Close your eyes and think of England.” But, for a middle-aged woman in “a committed relationship with a nice partner,” she believes that it’s a sound approach to improving a couple’s sex life.

Greenwald told Kristen that she needed to do some cognitive reframing. “Instead of asking, ‘Do you want me?’ ”—an epic question, requiring an epic answer—“couples should practice asking, ‘Hey, do you have five minutes?’ ” Sex, Greenwald often says, begets more sex. Her date-night tip: when out to dinner with their husbands, women should carry some travel-sized lube and pop into the ladies’ room to apply it right before dessert. “It’s hard to walk around with a wet vagina and not feel turned on,” she said.

One of Greenwald’s strategies is getting patients to practice inwardly narrating the sequence leading up to sex: He’s rubbing my back. I’m breathing a little faster. I feel warm. The goal is to banish the more common inner-mom monologue: He’s touching me. Did I remember those snacks for tomorrow? How will my daughter feel if no one asks her to prom? As with meditation, Greenwald said, patients gain control over their thoughts: “If it’s a Tuesday night before sports pickup, this is how you create good, efficient bedroom sex with your spouse that doesn’t involve a whip and leather boots.”

To keep the routine going, she advises couples to replace postcoital sweet nothings with compliments like “I love how efficient we were!” The idea is to tap into “that reward system where you have sex, you sleep well, you wake up more energized, you guys kiss before he goes off to work, you feel more loved by him, and the next night happens.” Describing why Greenwald’s methods work, Nathalie Dompé reached for an Italian phrase, “La fame vien mangiando”—the hunger comes while you’re eating.

It’s no surprise that expensive concierge medical care is better. It’s a particularly distressing example of how, in our society, necessities are becoming luxuries. Concierge care is innately problematic; when the wealthy can buy their way out of public-health problems, it reduces pressure to fix them. Gynecologists typically book fifteen-minute appointments: five minutes to do a breast exam and a Pap smear, five minutes to talk, and five minutes to document the visit. Greenwald gives patients as much time as they need, often an hour or two per visit.

“I think the system is broken,” she told me. Greenwald’s medical career was a form of response, stemming from her own experiences. When the COVID-19 pandemic hit, she felt herself beginning to crack.

Growing up near Stanford, in a close-knit family, as the granddaughter of a Stanford doctor, Greenwald had a vision of herself being an ob-gyn at the university—delivering babies at the same hospital where she was born—and having four sons. She became chief resident at the ob-gyn program at the University of California, San Francisco, and married a pediatrician, Daniel Imler. Throughout the eighty-hour workweeks of the residency, where she was permitted to take off only a month after the birth of her first son, she found herself going against protocol to co-sleep with the baby, because it was the only time she saw him. Passionate about health equity, she did a master’s degree in public health at Tufts, but she became disenchanted with the population-based approach it taught: she saw suboptimal high-volume care, in which the health of the individual was sacrificed to cost considerations, everywhere.

Medicine suited her personality. “I’m a little hyper, driven, anxious,” Greenwald told me. “But it works in medicine, because I am always worrying about excellence, perseverating on my patients.” In a public-health setting, that was the wrong mind-set. Only easy patients got good care, because time-consuming workups or expensive tests—let alone innovation—were prohibitive.

At thirty-two, Greenwald joined a Stanford health-care practice made up of four women and a man in Menlo Park. There, she saw up to twenty-five patients a day. She and her partners were perpetually overworked, and there was tension in the group because they had to cover for one another if they or their kids were sick. Back-to-back overnights left Greenwald exhausted and depressed.

When she was thirty-six weeks pregnant with her second child, Greenwald was in the middle of a seventy-two-hour shift—subsisting on saltines and cranberry juice between deliveries—when she went into premature labor. “He went home at four pounds,” she recalled, of her son. When COVID began, she discovered that she was pregnant again. Wearing an N95 mask so that she could nap in the hospital during patients’ long labors, she was anxious about her fetus.

At one point, the head of the practice asked Greenwald to pay special attention to a wealthy patient, and so, for once, she was able to practice medicine the way she wanted to, spending extra time on the case and catching issues that might have gone unnoticed. Greenwald wasn’t able to give herself, or her regular patients, that level of care. After overnight deliveries, she would find herself driving home too fast in order to get there in time for her husband to leave for work; she would remind him to give the boys the breakfast she had prepped the night before and to get them to preschool, and then she’d try to squeeze in a twenty-minute nap before returning to the office. One day in 2022, she fell asleep at a red light with her boys in the back seat and finally decided to quit her job. But she needed to work, and she still wanted to practice medicine. By then, her husband was the medical director of Stanford’s Pediatric Emergency Department, but they had little savings. Their money had gone into a cozy Craftsman house in Menlo Park, and repaying medical-school debt and the salary for their nanny ate up the majority of Greenwald’s take-home pay.

Greenwald decided to open her own concierge gynecology practice with no obstetrics, initially setting a thousand dollars a year as a membership fee. Hers was the only such practice in the area, and she didn’t know if it would work. On the side, she consulted for primary-care concierge practices and spent three days a month at Santa Clara Valley Medical Center, teaching and delivering babies for underserved populations, a commitment that she has continued.

At her own practice, she decided that patients would never wait, that she would be available from 6 A.M. to 9 P.M., and that she would never have to cancel because she was delivering a baby. The office would provide spa-fluffy robes, heated towels, and premium teas. She would answer texts and calls at all hours, including on weekends, and would travel to patients’ pool houses for a quick infection check or meet them on the tarmac when they flew, in a private jet, up from L.A.

Greenwald obtained medical licenses in New York and Florida so that she could take care of patients’ extended families. She sees her patients’ adolescent daughters, arranging anesthesia for IUD placements (prescribed to treat painful periods)—something that is rarely done, even though the insertion can be excruciating. She advises inexperienced teen-agers that lubes containing additives are dehydrating and create micro-abrasions that can increase the transmission of S.T.D.s, and she helps them navigate hookup culture, in which choking, polyamory, and anal sex have become mainstream. Ella Hale, a recent college grad who started seeing Greenwald at fifteen, told me, “She said, ‘If you feel any psychological or physical discomfort during sex, I want to know.’ ”

Greenwald tracks all of her patients’ metrics: blood tests to check that hormones are balanced; Oura rings to show resting heart rates and sleep scores; glucose monitors to keep tabs on blood sugar; food-tracking apps for logging daily protein targets. She sends them to get thousand-dollar Grail blood tests (the fact that they are not covered by insurance is not an issue for the B.V.C.), which may detect cancer years before it appears on any scan, and full-body MRIs (two thousand dollars), and she reminds them to pick up sunscreen on vacations abroad, because European formulations are more effective than what we can get here. Because there is heart disease in Gisel Kordestani’s family, Greenwald referred her to a preventative cardiologist who had her take the Cleerly cardiovascular test, an A.I.-based analysis of heart CT scans which yields new insights. Kordestani told me that she didn’t care about wasting time or money: “Now I know my cardio risk is zero.”

Greenwald focussed on optimizing her own well-being, too, waking at four-thirty to work out, and then answering patient e-mails while sipping bone broth or water mixed with psyllium husk (for fibre) and creatine. She attended conferences and pored over the latest research.

She had a fourth son, and her time felt more valuable than ever. She raised her prices a few times. Consultations became a thousand dollars, then two thousand. She decided to accept new members with tiered annual fees, starting at ten thousand dollars and exceeding thirty thousand for the most extensive care, which can involve assembling a specialized care team to monitor complex comorbidities. Then she stopped accepting the ten-thousand-dollar patients. What was the market price for this kind of care, she wondered. The influencer and doctor Peter Attia has a longevity practice with patients who pay six-figure membership fees. Clearly, there was room to keep going up.

One afternoon, I sat in on another appointment of Greenwald’s, this time with a patient in her fifties who had been diagnosed with early-stage breast cancer. The woman, whom I’ll call Lily, was agonizing between having a lumpectomy, which would entail taking the estrogen-blocking drug tamoxifen for five years, or getting a double mastectomy. Her oncologists were hedging, telling her that it was a personal choice. She knew that tamoxifen would curdle her sex life by inducing abrupt menopause; she was already struggling with symptoms of perimenopause, which her primary-care doctor had dissuaded her from treating.

Lily had an active life of golfing, skiing, and boating with her family. In the examining room, she sat on the table with Dior sunglasses perched on her head, wearing a ruffled, checked blouse and jeans—a California trad-wife look. Greenwald got her talking about her life, and her hopes for grandchildren one day. After a moment’s thought, Greenwald told her to do the lumpectomy—and the tamoxifen, which would cut the chance of cancer recurrence in half. She surprised Lily by recommending that she simultaneously do hormone therapy—a vaginal application, such as estradiol cream—to mitigate her symptoms. “Take some tamoxifen and know that, if you need a partner to respond to whatever shitty symptoms you’re dealing with, I’ve got you,” she said. “We’ll be creative.” She offered to send Lily a new academic paper on H.R.T. and cancer risk. If Lily ended up losing her sunny disposition, Greenwald said, they could explore solutions, such as Duavee, an estrogen replacement now in trial with high-risk women; contrary to conventional wisdom, emerging data seem to indicate that this form of estrogen is associated with a decrease in breast cancer.

“Duavee is blowing my freaking mind,” Greenwald said.

“Am I a good dog who sometimes does bad things or a bad dog who sometimes does good things?”

Cartoon by Amy Hwang

While mainstream oncology supports using local vaginal hormones that have little systemic absorption (although some doctors remain reluctant), the use of systemic hormones for women who have had breast cancer is contentious. “This is a Pandora’s box,” Mark Moasser, a U.C.S.F. oncologist and cancer researcher, told me. “It remains a field with different data sets and studies and different opinions and judgments. There shouldn’t be a ‘one size fits all’ guideline. It’s a matter of judgment between the doctor and the patient. I can’t say it’s ‘safe’ because we simply don’t know.”

Having dealt with Lily’s cancer questions, Greenwald pivoted to her sex life. Was it A+? Greenwald suddenly included me in the conversation, breezily asking, “Do you two have internal orgasms?” Lily and I both looked at her, agog. Greenwald has a crisp, matter-of-fact manner. With her practiced explanations and gestures, she could almost be a flight attendant explaining preflight safety protocols.

Only one in five women climax through internal stimulation alone, Greenwald said. Many never find the mysterious G-spot. But the G-spot becomes increasingly important in middle age, because women can’t rely on their old sexual responses to stay the same. “The clitoral nerve has two different nerve fibres, right?” Greenwald went on, as Lily and I nodded dumbly. This nerve root runs both internally and externally, ending in the clitoral nub, and it contains two different types of fibres, one of which responds to light touch and warmth, and another that senses vibration and pressure. But as we age, she noted, the fibre that responds to light touch and heat degrades, whereas the one that senses vibration and pressure maintains sensitivity. After menopause, with insufficient estrogen to nourish the tissue and facilitate blood flow, the clitoris starts to lose its sensitivity, resulting in poor-quality orgasms. (I had never heard of poor-quality orgasms.)

“So you’re going to come in here at some point, be it on your tamoxifen journey or when you’re eighty-five, and say, ‘We’ve done this position for forty years, and now it isn’t working.’ ” Greenwald counsels women to practice finding the G-spot and stimulate the deep internal nerve fibres that remain robust.

“Do you have a vibrator?” she asked Lily. The answer was an enthusiastic yes, and Greenwald offered to provide instructions for exercises to try at home. If the G-spot proved elusive, Lily should come back and Greenwald would show her where it is. Wrapping up, Greenwald said, with feeling, “I support you and your energy and your sex life and your orgasm quality and your vagina and your pelvic floor.” She looked Lily in the eye to make sure she heard it. Her parting words: “I’m on your team.”

With four boys under the age of nine, Greenwald has organized her family life so that it functions like a well-run startup. One night, she invited me to her house for dinner. Wearing sweatpants and a T-shirt, she jiggled her plump baby and showed me a mudroom where each of the boys has a cubby near a refrigerator that holds their lunches. “I am obsessed with systems,” she said. Outside the mudroom is a large touch screen that her sons are supposed to stop at and check off tasks on a schedule (“Eat breakfast and clear dishes.” “Sit on toilet and count to 30!”); each time, the screen rewards them with an explosion of confetti. Greenwald coaches the boys on social behavior: “Look at Melanie when you talk! Can she see your eyeballs?”

The house is colorful, with wallpaper covered in giant leaping zebras. One of her sons showed me his pet rabbit; another introduced a large parrot squawking in a cage. There is also a lizard, four hermit crabs, a toothed frog, and a wall-size fish tank that the kids built with their father; its filtration system is based on the workings of a kidney. Greenwald’s husband had just returned from a monthlong stint in Rwanda, teaching pediatric urgent care. Their nine-year-old had joined him, playing the role of patient. Like his wife, Imler is plainspoken and believes in cutting to the chase. “Sometimes I hear doctors cloak the news of a child’s death in so much flowery language that the parents don’t grasp what’s happened,” he told me.

Imler said that he admired how Greenwald likes to talk about “difficult things with people because it feels real”; he is amused by what he described as her impatience with fiction and art. “Her response to ‘Phantom of the Opera’ is ‘There’s a phantom—why are we singing about it for hours? Put him in jail!’ ” He thinks that part of her appeal to patients is that she is unfazed by their net worth. “Sally will not bow to you,” he said. “And people love that.”

Greenwald regularly gets together at a restaurant with concierge-doctor friends. At a recent gathering, over drinks and meze, they talked about the coolest new things they are doing for their patients. Justin Lotfi, a primary-care physician to a fortunate few, offered that he’d been experimenting with a nasal procedure using an anesthetic that, with repeated applications, can break a cycle of migraines.

“I love being in concierge medicine, because practicing at the top 0.001 per cent—that’s where innovation happens,” Greenwald told me. “I get to sit around and think about these things.” She went on, “I am always, like, ‘What’s next? What’s better? Why don’t we try this?’ ” She added, “But at some point the system needs to evolve so other people can access this kind of care.”

Midi Health, a virtual-care platform for women in menopause and perimenopause which was founded in 2021, offers the same sorts of hormone treatments that Greenwald does, including options for cancer patients, and it accepts insurance. Joanna Strober, the entrepreneur behind Midi, supports Greenwald’s approach, but told me, “I am sad that women believe they have to pay all that money to get menopause care.” She added that Midi does most everything that Greenwald does “without the in-person component.” When Strober was raising money to start Midi, male venture capitalists told her that menopause was “niche”; now Midi has a billion-dollar valuation.

To help close the gap in medical care, Greenwald is trying to publicize her ideas, through her book and public speaking. Last fall, she was a guest on Peter Attia’s popular medical-and-life-style podcast, “The Drive.” When she got to the importance of lube for vaginal health, Attia pushed back, repeatedly questioning whether young women needed lube, since reduced friction might detract from a man’s enjoyment of sex. Greenwald held firm. The episode ended up having “The Drive” ’s highest ever Day One-download count on Apple metrics. Three months later, when a batch of files about Jeffrey Epstein was released by the Department of Justice, Attia’s name turned up more than seventeen hundred times. In one bit of banter from 2016, Attia e-mailed Epstein, “Pussy is, indeed, low carb. Still awaiting results on gluten content, though.” In another exchange, Epstein muses to Attia that he’s not sure why “women live past reproductive age at all.”

After the Epstein news broke, the Post published a snarky piece about Greenwald’s episode of “The Drive,” and internet critics piled on. Greenwald declined to comment on Attia, with whom she shares patients, but said that she is eager to engage with the manosphere, including on platforms associated with toxic masculinity. That, she said, would be “a great way for me to push this agenda to an audience that is not typically listening. If there are chances to spread my message that sexual health is health, I’ll take that opportunity every time.” ♦