Dr. Jeffrey Spiegel, a Boston facial plastic surgeon, performs about 1,200 surgical procedures a year—but that’s not what sets him apart from other top doctors. He’s been making masculine faces look more feminine for 20 years, and sees more than 30 transgender women a week for consultations or procedures. One of these women is Valerie, who considers Dr. Spiegel one of the best surgeons in the country for the procedure that, for most of her life, she doubted she’d ever have.

“As early as age 8,” Valerie says, “I remember feeling profoundly distressed that my male body wasn’t the right body. That feeling never changed, though I remained in the closet for most of my life. I’m 66 now, and I’ve just recently come out.

“Before I transitioned, I thought the choice was fairly stark: Either I’d continue to live as a man, which meant continuing to live a lie—or I’d come out and blow up our lives. I met my wife when I was 18 and she was 17, and we’ve been together ever since. I’m an attorney and had a fairly high- profile career before I retired. I was afraid that if I came out, I’d lose my friends, my business associates, and maybe some of my family. Those kinds of thoughts are very heavy to carry around.”

What is facial feminization surgery?

“When trans women come to see me,” Dr. Spiegel says, “it’s because their faces are sending the wrong message. Inside, a trans woman knows who she is, but her features convey an inaccurate identity. So we look at the face and ask, “What’s sending the wrong message?” Often, it’s a process of changing bone shapes and light reflections. Those changes convert the face to clearly send the message of ‘female.’”

Dr. Spiegel’s patient—not Valerie

“Facial-feminization surgery represents the best of what plastic surgery can be,” Dr. Spiegel says. “It uses all our technical skills, creative skills, and medical knowledge. It changes peoples’ lives substantially for the better by aligning their sense of self with their presentation to others.”

Dr. Spiegel’s patient—not Valerie

The psychological toll of gender incongruence

“I shared my gender concerns with my wife back when we were really young,” says Valerie. “In the early 1970s, we didn’t have a word for what I felt. The term transgender didn’t exist—at least, not to my knowledge.

“Then, in the mid-1990s, with the advent of the internet, things changed. Suddenly, I had access to wide-ranging information. I came across the word transgender, and around the year 2000, my wife and I had many long talks about it. But we were raising three kids, and I was in the midst of an exploding career. There was no chance that I was going to be able to come out. At least, that’s what we thought at the time.

“We decided to keep my deeply held secret. But as the years went on, my thoughts turned darker. My anxiety increased, and I began to think that maybe not being around at all anymore would be easier than bearing that burden.”

How Valerie met Dr. Spiegel

“One of the real lifesavers for me,” Valerie says, “was that around 2011, I attended a major transgender conference. I met hundreds of people in circumstances similar to mine and heard the sponsoring doctors speak about various surgeries and hormonal therapies. Dr. Spiegel impressed me as a heavyweight surgeon with heavyweight credentials, working at a heavyweight institution. I wasn’t an immediate prospective client—but I was curious.

“At the time, I had a profoundly male face—a pronounced forehead, a large cleft chin, and other ultramasculine features. One of my biggest fears was appearing like the Bud Light guys wearing dresses in that mid-’90s “Ladies Night” TV commercial. That’s not an attractive image, and it’s not what I wanted to project to the world.”

What makes facial-feminization surgery unique

“Most plastic-surgery textbooks teach people to analyze faces using a mathematical analysis,” says Dr. Spiegel. “A nose is supposed to be a certain proportion; the face is supposed to be a certain width or length. This is in all the books, but it’s wrong.

Dr. Spiegel’s patient—not Valerie

Our brains don’t judge gender or attractiveness based on mathematics. It has [more] to do with shadows and reflections—how patterns of light and certain bones appear. A lot of minute things work together to completely change how a face is perceived.

Dr. Spiegel’s patient—not Valerie

Valerie’s transition

“To me,” Valerie said, “transitioning meant finally telling people that I’m transgender—and living my life as truthfully as I could. I came out first to my family, and they were, to a person, loving and supportive. But certainly, they didn’t see it coming. I know that many transgender people don’t have families who are supportive and loving and don’t have a spouse who’s willing to go the distance with them. I’m very fortunate in that regard. We’re fortunate to have each other.

“Telling our friends was difficult for both of us—but particularly for my wife. She’d married a man, not a woman. While she loves and supports me, we both knew this would change how she presents to the world. I kept saying, ‘Imagine you have a Stop button. At any point along this process, if it’s too much, just hit the button. We’ll stop, we’ll stop.’ But she never did.”

How Valerie came out

“We told a few people in person and then wrote letters to 65 of our closest friends, telling them that I’m transgender. I’ll never forget how frightened I felt, standing in front of that mailbox, knowing that once they dropped, there would be no taking it back. But my great joy in life is that we chose our friends well. The responses came right away, and our entire friend group was incredibly supportive.

“I’d also resigned from the large law firm where I was working as a consultant before I came out. I didn’t want my situation to somehow come back to—in my view—taint their reputation. They rejected my resignation and insisted I stay on. And they changed the letterhead to reflect my new name.

“In the end, all our biggest fears proved to be completely unfounded.”

Valerie’s surgical procedures

“Facial-feminization surgery varies considerably from patient to patient,” Dr. Spiegel says. “But feminine faces have a certain bone structure. There’s a certain size of the eye, compared to the rest of the face. There’s a certain brightness around the mouth, a certain lack of bone of the forehead, so a cranioplasty and lip lift are often important. There’s a certain fullness to the cheek—but not laterally, more to the front. Reducing the Adam’s apple is simple, but it must be done in a precise way so you don’t ruin a person’s voice.”

“Some transgender people don’t want—or feel they need—any kind of surgery,” Valerie says. “It’s a highly personal decision, and no one should feel pressured. But for me, it felt necessary to align my body with the gender I was born into, which is female. So I had forehead surgery, eyelid and jaw surgery, rhinoplasty, and cheek implants; I had my Adam’s apple and cleft chin reduced. Altogether, it was an eight-and-a-half-hour procedure.”

Valerie’s recovery

“The first days after surgery, I looked like I got hit in the face multiple times with a baseball bat. I was really a mess, but I expected that. Dr. Spiegel said to me, ‘Look. You’re having the jaw reduction done. That’s going to produce the most swelling. Two months out, your jaw will be as big or bigger than it ever was. Give it time. It’s going to be at least four months before you can see the results we saw in the operating room.’ He was spot-on with that prediction.

“Now, if you compare my pictures, I don’t look like the same person I did before. The face looking back at me is very close to the face I’ve always felt I should have. And that’s had a profound impact.

“I don’t have any of the anxiety, the stress, the dark periods of sitting in the living room by myself after my wife went to bed, thinking about what to do with myself,” Valerie says. “Those are all gone. I wouldn’t go back to my old face for a million bucks.”

Completing her transition

“In my personal experience, there were three stages to transitioning,” Valerie says. “The first was when I came out to all my friends and family. Some were shocked and bewildered, and many didn’t truly grasp what it means to be transgender. The second was when they met me for the first time in my new presentation. That was distressing for all of us—I was so worried about how they’d react and how they’d perceive me.

“And then the third phase—which is where I want to get—is when I finish a day of skiing and go to the place we always go to have a beer. I arrive before my friends. One of them walks in and says, ‘Hey, Valerie. Do you know how to get a beer around here?’ Then I’m no longer the focus of attention. I’m no longer something unusual—I’m just a friend. At that point, it’s complete.”

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