UrbanUpdate

Evan Goldstein is a surgeon working in New York City and perhaps the world’s most notable medical expert on anal sex. This is a line of work that sometimes requires a sense of humor. Or, as he tells me, “It’s one life we all get—why not be able to take it up the ass if you want to?”

This work is also something Dr. Goldstein takes extremely seriously. To Dr. Goldstein, there’s a society-wide tendency to devalue anal sex as a “nice to have” rather than a “need to have,” and this does not align with the reality of a huge number of people. Gay men, for example, are often told, even by otherwise LGBTQ-friendly health practitioners, that if bottoming hurts, they should simply stop bottoming. He points out that this is advice that I, as a straight woman, would never be given if I told my doctor I found vaginal penetration too painful to engage in.

“Think about it—if your vagina didn't work, how catastrophic that would be,” he says. “And it's the same thing from an anal perspective. If someone has desires to take it up the ass and can't do it, they’re distraught. It ruins relationships. It fucks with your psyche. I’ve seen people who are suicidal.”

Traditional anal health care tends to be narrowly focused—“Are you shitting correctly?,” as Dr. Goldstein puts it. He says you can’t adequately treat patients who engage in anal sex with this approach, so he offers these patients a safe space for them to discuss goals that go beyond being able to have a painless bowel movement.

Patients typically find him after long, frustrating journeys through the health care system that typically involve zero conversations about sex. When they get to his office, on the other hand, “I need to know first what the patient is actually doing, and what they want sexually,” he says. “Do they want fists? Are they doing huge toys? Are they just doing external play? ”

At his medical practice, Bespoke Surgical, he caters primarily to the LGBTQ community, but can and does offer care to “anyone with an asshole.” He listens to the answers to those questions and offers services to help: surgery to repair tears, Botox injections, referrals to physical therapy. Many of these treatments take only 10 or 15 minutes but have life-changing results. “I get emails from people who are able to have sex with their partners after not having been able to forever,” he says. “It's such an amazing feeling.”

Much of Dr. Goldstein work has come to focus on education: how people prepare their bodies, how they engage sexually, and what they do for aftercare or if something goes wrong. The desire to destigmatize and demystify these topics is what motivated him to write his new book, Butt Seriously: The Definitive Guide to Anal Health, Pleasure, and Everything in Between, which was published last month (complete with a blurb from sex columnist Dan Savage).

On podcasts and in magazine articles, he’s an increasingly visible demystifier. “Few people know how to engage in anal sex properly,” he says. “Everyone thinks they can just shove the thing right in.”

Dr. Goldstein didn’t grow up dreaming of becoming an anal expert. He studied to become a heart surgeon after seeing the 1990 film Flatliners, and, during his residency, he met and married a fellow surgical resident, a woman. Upon graduation, he was hired as the one surgeon admitted each year into the heart program at Mount Sinai Hospital in New York.

His life was ticking all of the boxes, but in the background he was struggling with his sexual identity. He had begun to wonder if he was gay, and became intensely conflicted about that piece of self-knowledge and the plain fact that he was married to a woman he loved.

He started testing the waters by visiting online chat rooms for gay men in their 20s. It was there he met Andy, a man he would eventually fall for. For a while, he remained silent about what was going on, but it was taking a very obvious toll on him, and his parents noticed. “My mom calls me, and she's like, ‘You're sick all the time. You've lost 40 pounds. Something's not right. We've made a list of certain things we are concerned about.’ And number one was, ‘Are you dying?’ And then number two was, ‘Are you gay?’ And I just broke the fuck down,” he says.

At one point in the midst of this crisis, he says Andy presented him with three options. “You can continue your married life, you can come out and be gay and enjoy gay life and learn who you are, or you come out and be with me’,” Dr. Goldstein recalls him saying. “I didn't think it was that simple, but it clearly was.”

The two are still together, 18 years later, but it wasn’t the end of his confusion about how his life should go. He had also begun practicing heart surgery only to discover that he hated it—which led him to quitting his dream job just two weeks in. “The head of heart surgery was like, ‘You don't know what you're doing—what the fuck is wrong with you?’” Dr. Goldstein says. “So I put my pager down and left. And then, as I was walking to meet Andy in Central Park, I said to myself, You know what? I am gay, and I’m so proud of it.”

He took a job with an old boss, mostly doing gallbladder, hernia, and other “run-of-the-mill” surgeries. But he was simultaneously exploring his new sex life, and in the process he realized that an earlier anal tear—resulting from poor diet and habits—was going to hinder his ability to enjoy anal sex. It wasn’t the end of the world for him, but he wondered who was caring for those in his community for whom being able to bottom was a priority.

“Andy was like, ‘Who gives a shit? If you have an anal problem, you'll just go to an anal surgeon. Why does it have to be a gay surgeon?’ But I thought it really mattered, so I started to look around to find out who was taking care of people surgically if something goes wrong, and who was educating this population,” he says. “I realized nobody was doing it, so I said, ‘Fuck it, I don’t care if I fix someone's heart or I fix their ass, as long as I'm helping.’” Dr. Goldstein hung up a shingle for Bespoke Surgical.

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Fifteen years later, he sees 90 patients and performs 15 surgeries a week. His Instagram bio includes the words “vintage Porsche collector.”

But in the early days, he worried about the viability of his business plan. Despite the fact that there were a lot of people in need of anal care and education, not many people were talking about it. “I did a study early on in my career,” he says, “and what I found was that even 92% of gay providers were not talking about gay sex with their patients.” That meant Bespoke Surgical might not work—he needed doctors to refer their patients to him, which they weren’t going to do if they hadn’t properly identified what was causing issues for their patients, or factored their patients’ goals for painless and pleasurable anal sex into treatment.

At the time, he says, he had no specific training relevant to what he was trying to do, because such training didn’t exist. But he quickly found success by relying on his surgical training and listening to his patients. “These techniques have evolved because I looked at the community and said, for example, ‘Oh, you want to take that thing, but you can only take this thing. So, I need to create more room—how are we going to do that?’” he says. “Can I create more room by giving you anal Botox? By having you do physical therapy and using different toys to stretch a bit more? Or do we need to try a surgery to get you into a good space?” Years of refinement went into developing a six-week anal dilation plan designed to help the two-thirds of the population he says can’t easily engage in anal sex. He worked with trans-fem patients to understand how estrogen therapies thin out the skin of the anus in a way that can make sex fraught.

Connecting the dots on common patient issues made him realize how harmful many common practices were. In particular, he saw problems caused by pre-sex douching. This led him to wonder why there weren’t better, safer products on the market, which in turn inspired him to create a better washing device, which became the first product launched by Dr. Goldstein’s second venture, the sexual-wellness company Future Method.

Open dialogue with patients and the public also allows him to educate about best practices when it comes to anal health and anal sex. “If you start to answer your own questions, now, suddenly, you’re able to take care of all of it,” he says. And Dr. Goldstein has much wisdom to impart. He says most people are ill-informed when it comes to the ways in which diet and hygiene influence anal health and anal sex. “People don’t know how to poop,” he says, adding that they also don’t know that things like wet wipes are a no-no, that they need to be showering at night after presumably having a bowel movement sometime during the day, or that loose-fitting clothing will help the area breathe.

If that sort of information is interesting to you, Butt Seriously has much more. That’s a message he says hasn’t always been easy to get out. Publicity around the book can sometimes be a hard sell. He’s limited by what he can casually discuss in many media spaces. “I can’t talk about gay sex, I can’t talk about anal sex,” he says.

But be believes that if people were engaging in all kinds of more-open conversations around sex and health, it could change lives.

“Why didn't my mother say to me, ‘Evan, what type of sex are you thinking about?’ I missed out on so much by hiding who I was,” he says, “and I think about how many people don’t get to experience their true selves.”

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