A recent portrait of Dia Dipasupil.
Marcus* was nine and Nick* was four when their dad explained that he was going to start a new life as a woman. In several conversations, Dio Dipasupil, married and in his early 40s, would sit down with his boys at the family’s home in New Jersey and basically say, in very simple terms, that Daddy felt better being a girl. That he wasn’t happy with himself as a man and was happier as a woman.
“And they kind of get that,” Dipasupil told me. “They understand that.”
For years Dipasupil had lived a dual life: outwardly he was a typical suburban dad, married to a woman he had met in his 20s while they both worked at Macy’s and a proud father who liked motorcycles and gadgets and enjoyed roughhousing with his kids. He was a lean five foot four, with short black hair and dark eyes and a broad white smile, and had recently left a long career in IT to become a photographer. But inwardly Dipasupil was tormented. Unable to express what he felt was his true gender identity, he sought release in alcohol and drugs. He became suicidal, frequently fantasizing about taking a long, quick leap from the George Washington Bridge. After one particularly low night, when he had drunk himself into a stupor in Manhattan and ended up lost, beaten and robbed, Dipasupil realized he couldn’t keep living as he was. So he didn’t. But Dipasupil didn’t jump. Instead he wrote a letter, posting it first on the blog he maintained at the time and then on Facebook, in order to reach more people. Dated January 17, 2010, it was titled, vaguely, “An Open Letter To All My Friends…” It began:
This is one of the most difficult letters I’ve ever had to write. I’m not sure how to start, so I’ll follow my thoughts from recent discussions with my family and close friends.
Since my earliest childhood memories I’ve struggled with something that has brought me much pain in my lifetime. I thought I could suppress my feelings, but unfortunately those feelings would always win. My reluctance to share these feelings with my family and friends over time has lead to many health issues, emotional torment, and clinical depression for me. “Several years ago my bubble burst and I realized I couldn’t continue living miserably and faking it like I have all these years. I started seeing a therapist in NYC and came to the realization of what I’ve known for some time… that I’m transgender (and more specifically, transsexual). In other words, I don’t identify with the gender I was assigned at birth and I’m uncomfortable in my own body. My subconscious sex is not aligned with my physical sex.
Then, towards the end of the letter, right before a list of Frequently Asked Questions about the transgender community, Dipasupil bade his farewells:
I hope you will familiarize yourself with the transgender spectrum. More importantly, I’m hoping that all of you will choose to remain in my life as I embark on this journey. If some of you don’t, that’s okay. I understand and will miss you, but this is who I am, and can no longer deny it.
…I intend to permanently deactivate this Facebook account in the coming weeks. I welcome any friend requests at my new Facebook account. I hope to see you there. ”
In the new edition of the American Psychiatric Association’s Diagnostic and Statistical Manual of Mental Disorders, released in May, the term “gender dysphoria” is used for the first time to describe “a marked incongruence between one’s experienced/expressed gender and assigned gender.” The term replaces the more explicit “Gender Identity Disorder,” which had been used since 1980, the first time any reference to transgenderism appeared. For many transgender and civil rights advocates, the rewording—specifically the removal of the word disorder—represents a significant victory in the march towards tolerance, something analogous to the APA’s removal of homosexuality from the DSM altogether in 1973. Labeling transgenderism as a medically diagnosable disorder, the theory goes, serves only to reinforce or even justify a subsequent cultural prejudice of the transgendered as inherently wrong. Removing the disorder distinction is intended to have the opposite effect, to lend medical legitimacy to the opinion—held by many transgender, but not all—that transgenderism is not a disorder or pathological abnormality that needs medical correction but simply an alternative and equally valid expression of identity.
“All psychiatric diagnoses occur within a cultural context,” explained Jack Drescher, a leading gender identity psychiatrist and a member of the new manual’s Workgroup on Sexual and Gender Identity Disorders, to the magazine in July 2012, following the announcement of the planned change. “We know there is a whole community of people out there who are not seeking medical attention and live between the two binary categories.” In other words, Drescher was saying, it’s OK if you’re transgender and feel you don’t want or need to transition towards one sex or the other—and neither should it be your psychiatrist’s place to tell you otherwise.
It was a rare moment of formal consideration for what remains, perhaps, this country’s most stigmatized and least understood demographic. In the United States there are an estimated 1 to 3 million people who identify either as transsexual (meaning their biological sex does not conform to the gender they most identify with) or as transgender—the broader umbrella term that can be applied, if sometimes contentiously, to anyone whose gender identity falls in some way outside the typical male-female binary. The transgender range, broadly, from some crossdressers at one end of the spectrum to those who have undergone genital reconstruction surgery at the other. And while in recent years the transgender people have made real strides toward cultural visibility and acceptance—in late 2009, for example, Amanda Simpson became the first openly trans presidential appointee, and over the past several years numerous elite colleges have begun offering student health care plans that cover sex-reassignment surgery—on the whole trasngenderism still remains largely taboo in mainstream American society. Where it is generally no longer socially permissible to publicly ridicule or discriminate against gays or Jews or the handicapped, it is still acceptable to openly target the trans community.
In March, for example, Saturday Night Live aired a mock movie trailer for a romantic comedy starring Justin Timberlake called “She’s Got a Dick." Last December, a Colorado elementary school drew attention for barring a six-year-old who identifies as female, Coy Mathis, from using the girls’ room at school because several years down the road her classmates might feel uncomfortable about her male genitalia. And in February, it was still acceptable for an Arizona assemblyman, John Kavanagh, to propose a bill—clearly aimed at the transgender—that makes it a misdemeanor for someone to use a public restroom facility designated for one sex if his or her birth certificate says another. “There are laws to cover racism and sexism and homophobia,” said Finn Brigham, special populations director at Callen-Lorde Community Health Center in Manhattan, the largest LGBT health center in the world. “And those are super important and those came out of years of pushing for those laws, but the fact that they don’t exist in most places for the transgender population—that’s blatant discrimination.”
Like many on the transgender spectrum, Dipasupil’s gender incongruity started early. Beginning around the age of four, little Dio would wake up early in his family’s small Bronx apartment, before anyone else was up, to sneak into his little sister’s closet and try on her dresses. They were light colored, Dipasupil still remembers, pretty pinks or pastels or whites. “At that young age there was nothing sexual about it,”Dipasupil said. “It was—I felt good wearing it. I wanted to wear it.”
As Dipasupil got older, his desire to wear women’s clothes, to his deep regret, only grew stronger. The clandestine visits to his sister’s—and then his mother’s—closet became more frequent, and the risks he took to slip into their skirts or panties or cocktail gowns grew more pronounced. By the time he was a teenager, his habit engendered a crushing amount of guilt and shame; the five Dipasupil kids, children of Filipino immigrants, a doctor father and a nurse mother, were raised strictly Catholic, but Dipasupil still couldn’t help himself. He dove headlong into sports, music, model building—anything to distract him from what had become an insatiable urge to wear women’s clothing. But even if for several years the distractions “kind of worked” (at least enough to allow Dipasupil to keep hoping that one day he would somehow beat his feelings or that they might simply disappear), the urges would always come back. His desire to dress—to feel—like a woman would never go away.
All those years of sneaking into closets, Dipasupil was never caught—he told no one of his secret until he confided in a long-term high school girlfriend and, a few years later, a college girlfriend. Both took the news relatively well, reacting with curiosity, perhaps, but not scorn or excessive shock. So did Catherine*, the Macy’s coworker who would eventually become Dipasupil’s wife and the mother of his two children. “She was fine with that for a long time,” Dipasupil explained. “Even when I started going out publicly she was cool with it.”
She was fine with crossdressing, that is—Dipasupil wasn’t. For years he tried to convince himself that wearing women’s clothing and makeup was the extent of it, that he was just a guy who needed to occasionally express a feminine side. Once he became serious with Catherine he had hoped, too, that settling down might finally cure him, that getting married and embracing a typical American lifestyle—kids, steady job, house in the suburbs—would somehow make him feel like a typical American man.
It didn’t. His gender incongruity never went away.
“Honestly I thought about it almost every second,” Dipasupil said. “Every other minute, it would always come up in my mind. That was always what I was thinking about.”
Dipasupil's driver licenses before and after the letter.
Within minutes, Dipasupil’s letter inspired more than 200 comments on Facebook. They came from friends, colleagues, and family members—all expressing unabashed support for such a courageous life decision. “In the early days people were very supportive,” Dipasupil remembered. “It was a big surprise to them, so their initial reaction was to be supportive.”
For most of the commenters, the letter was the first time they learned of Dipasupil’s gender incongruence. Who would ever have suspected that Dio—shorthaired, married, typical straight-guy Dio—would ever be anything other than who he had always presented himself as?
For Dipasupil the letter marked the beginning of a new life—her public life as a woman. But as much as it was the beginning of one journey, it was also the culmination of another: As far back as August 2007, nearly two and a half years before he would come out full-time, Dipasupil had begun presenting himself as female in public about once a week. It was actually his therapist’s idea. “She said to me one day: ‘Well, how do you really know that you feel this way and that you want to live as a woman? You’ve never been out and interacted with anybody as a female.’”
So Dipasupil did some online research and found a transgender group that met on Thursdays at Nowhere Bar, a gay bar on 14th St., in the East Village. That first day—his big day—Dipasupil took the day off work to make sure he had plenty of time to prepare. He rode an early afternoon train from Hoboken to Manhattan, checking into the Union Square Inn, just a couple blocks from the bar, around 3 PM. Shortly after Dio became Devin. She applied light makeup and ditched her male cloths for spiked heels, tight jeans, a lacy black top, and a custom-made wig to conceal her buzz cut. “It was really low key,” Dipasupil said. “I just wanted to blend in. I just wanted to go out and be myself.”
Dipasupil stayed at the bar that night until 4 in the morning—closing time—lost in a strange kind of ecstasy. It was the first time in more than 40 years she had truly felt like herself. “It just felt right,” Dipasupil said. “I knew right then and there that this was meant to be.”
Nearly every Thursday night for the next year Dipasupil went back to the same bar, staying until closing and then “de-girling”—changing back into her male clothes in the bar’s restroom, making it back to New Jersey in time for work Friday morning.
In June 2009, six months before finally coming out, Dipasupil started growing her hair out and taking spironolactone, a testosterone-blocker, which gradually decreased her muscle mass and libido. Five months later she began taking estrogen, which softened his skin and began the development of small breasts and a more womanly distribution of body fat. But these changes were private, known only to Dio and Catherine. It was the letter that made it public. After it was published she began the process of officially changing her gender marker on her driver’s license and other documents. She eventually changed her name to Dia and was thrilled when she was hired—as a female—by the prestigious Getty photo agency.
Publishing the letter was the climax of Dipasupil’s journey. It meant she could be free, that she could be the same person outside as she was on the inside. But it was also the catalyst for a period of great personal loss. After Dipasupil went public, despite the initial outpouring of support, many people in her life began to fade away. A brother and sister who were once extremely close gradually slipped out of touch. The family get-togethers where the two Dipasupil boys played with their across-town cousins were no longer scheduled. A close friend—Dipasupil’s confidante since childhood—stopped returning calls. And Catherine, who had been along for the ride as long as her husband was “only” crossdressing, would soon be gone too—she had seen the letter before her husband posted it and pleaded with Dipasupil not to publish it, knowing full well that once it was out it would mean there was no going back. Dipasupil had actually hoped to try to work out some kind of continued relationship with the woman she loved—there were other couples, after all, who had managed to stay together after one transitioned—but Catherine wasn’t having it. She had fallen in love with a man. She wouldn’t—couldn’t—stay married to a woman.
The couple separated, although a divorce wasn’t finalized until January 2012—two years later—and Dipasupil remained living in the house until around the same time. When she was still living with Catherine and the kids, Dipasupil told me, she would tone down her female expression. She was careful not to wear too much makeup or appear overly feminine in front of the boys. But when Daddy has decided he’s going to grow his hair long and wear female clothes and take hormones that change his body and soften his skin, obviously some kind of explanation is needed. So Dipasupil would sit down and patiently explain where things were headed. She was going to become a woman, she would say, and her life was going to change dramatically. But none of that would change how much she loved them, she would tell her boys again and again. There was nothing that could ever change that.
The gender change, Dipasupil said, was actually less difficult for the boys than their parents’ divorce. “They were young,” she said. “It was fine with them. They just wanted to be loved.”
In Thailand, as many as several hundred thousand genetic born males—usually who from an early age display typically feminine traits like prettiness or daintiness—transition before adulthood to live the rest of their lives as females. Some ultimately undergo surgery, receiving breast implants, a vagina, and/or a thinner face. Others do not. But in some respects the physical details of the transition don’t matter much: The transgender kathoey, famously known to Westerners as ladyboys, are essentially a highly visible and generally accepted segment of Thai society. They are probably most famous for their roles as sexy cabaret performers or entertainers in places like Bangkok or Phuket—an indelible symbol of Thailand’s smiley, laissez-faire attitude towards all things sexual--but the kathoey also lead lower-profile lives as grocery store clerks, waitresses, flower vendors. And while they do face some official discrimination—Thai government I.D. cards, for example, list all kathoey as men, even those who have undergone genital reconstruction surgery—Thailand’s transwomen “nevertheless appear to enjoy a degree of prominence and acceptance unknown in most other places,” writes Sam Winter of the University of Hong Kong.
In southeast Oaxaca, Mexico, in and around the city of Juchitán, a segment of the population known as muxes (pronounced moo-shay) are similarly accepted by their indigenous Zapotec community. Also genetic males who live outwardly as females, muxes perform tasks usually assigned to women, like embroidery and home cooking, and are generally considered—and accepted—as a kind of third sex, an essential thread in the local cultural fabric. Each November an annual festival celebrates them, with men, women, and muxes from Juchitán and neighboring communities all descending on the town in their finest dress and the mayor ultimately crowning a muxe queen. A certain degree of variation exists within the muxe population—some embrace the female role and appearance more vigorously than others—but “what they share is that the community accepts them,” writes Marc Lacey in The New York Times in December 2008.
But mainstream American society, of course, has never offered up such a celebration of its gender nonstandard. Unlike the Thais or the Zapotecs, we have been conditioned to see gender as a binary, not a spectrum, and those outside of it—any gender outliers—have been treated harshly. In the mid 19th century, several American cities passed laws that forbade men or women from appearing in public wearing clothes of the opposite gender. In 1880, Lucy Ann Slater, a trans man who went by the name Joseph Lobdell, was committed to an insane asylum in New York for dressing and living as a male. In 1959, Christine Jorgensen, formerly George, the first American widely-known to have undergone a sex-change operation, was denied a marriage license upon trying to marry a man—and her fiancée was reportedly fired from his job once word of the engagement got out. More recently, in the decades since the LGBT movement began in earnest with the Stonewall Riots in 1969—led in part by a transgender woman, Sylvia Rivera—the transgender have still more often than not been an afterthought in the nation’s social rights consciousness. In 1976 the New Jersey Supreme Court rejected the appeal of a transgender woman, Paula Grossman, when she argued she had been discriminated against when she was fired as a result of her sex-reassignment surgery. In 1995 Tyra Hunter, a Washington D.C. transwoman, died after being denied emergency care because of her gender identity. And now, even as many school districts and universities and major companies are indeed making efforts at trans-inclusiveness, only 16 states and 143 cities and counties actually have gender identity non-discrimination laws in place.
For everyday trans Americans, the social consequences are not pretty. In the most well known study of its kind, a survey of more than 6,400 transgender people by the National Center for Transgender Equality and the National Gay and Lesbian Task Force that was released in 2011, nearly half of respondents reported having been fired or not hired or promoted because of their gender identity. More than one-fifth reported having been mistreated by police, and more than half reported experiencing family rejection. But by far the study’s most alarming finding was that 41 percent of respondents reported having attempted suicide, roughly 25 times the rate for the population at large. “It is part of social and legal convention in the United States to discriminate against, ridicule, and abuse transgender and gender non-conforming people within foundational institutions such as the family, schools, the workplace and health care settings, every day,” read the report’s scathing conclusion. “Instead of recognizing that the moral failure lies in society’s unwillingness to embrace different gender identities and expressions, society blames transgender and gender non-conforming people for bringing the discrimination and violence on themselves.”
Venus Xtravaganza, a transwoman and cast member of the film Paris is Burning, was the first transperson whose murder attracted widespread attention. She was killed in New York in 1988, reportedly strangled and stuffed under the bed in a hotel room. In 1993, Brandon Teena, a 21-year-old transman, was raped and murdered in Nebraska. In 1995 Channelle Picket, a 23-year-old transwoman in Massachusetts was murdered, then Rita Hester, also in Massachusetts, in 1998. Fred Martinez, Jr., in Colorado in 2001. Gwen Araujo, in California in 2002. Emonie Spaulding. Bella Evangelista. Nirea Johnson. Ruby Ordenana. Erika Keels. Dana Larkin. Sanesha Stewart. Larry King. Duanna Johnson. Felicia Melton-Smyth. Angie Zapata. LaTeisha Green. Tyli A Nana Boo Mack. Victoria Carmen White. Brandy Martell. All murdered. All likely because they were trans.
For the most part, Dipasupil is happy with her transition. After she came out publicly her blood pressure, high her whole life, instantly dropped to normal, the decades of built up tension having suddenly melted away. She’s at a greater peace than she was before—happier, more content with herself, more fun to be around. Her kids tell her this. But Dipasupil is also lonelier. She has few friends and no recent romantic interests. Everyone at the Getty agency, for whom she takes mostly celebrity and event photos, has been tolerant and respectful, she said. But still, even in crowds of tolerant, liberal photographers, Dipasupil will often find herself alone. “Someone will say ‘hi,’” she said. “And then they’ll disappear. They don’t want to be there standing with me.”
Dia shooting photos for the Getty agency.
On a Thursday night in early January the Stonewall Inn was only sparsely filled. Several patrons, mostly young, lingered at the bar waiting for drinks or chatting, as several TV screens flashed sexy images of provocatively dancing men and women and Lady Gaga blasted over the loud speakers. In one corner of the room, next to an empty stage demarcated by a velvet rope, a half dozen or so transmen and transwomen, mostly middle-aged, huddled around a couple red-felt pool tables. They cheered and laughed at good and bad shots, drank cocktails, chatted among themselves.
Dipasupil stood against the wall, slightly away from the group. She comes here often—she likes catching up with her trans friends, some of whom she’s known for five years, since she was just starting her transition. But Dipasupil doesn’t connect well with the trans community. There’s a lot of cattiness, a lot of divisions, and as much as she enjoys the company of the Thursday Stonewall group, she doesn’t feel particularly close to the community as a whole. “I get the sense they don’t like me sometimes, for whatever reason,” she said. “Maybe it’s not transwomen per se—it’s just women. The catty, competitive thing. I’m still learning those kinds of things too.”
After a couple hours, as the Stonewall was clearing out, the same group migrated across the street to another bar, The Monster. There they sat at a long table in a back corner, talking more, drinking more, loosening up and chatting with other patrons. One crossdresser from the group, tall and with a prominent jaw and heavy makeup, tight designer jeans and a $65 wig, introduced herself as Crystal. In the rest of her life she’s Chris, she said—a man, a philosophy professor at a college in New Jersey. She’s married, too, and so far only crossdresses once or twice a week, which seems to be enough. Her wife knows about it and is supportive up to this point, Crystal said, but “probably if I wanted to do anything more permanent that would be different.”
Later in the night a couple other transwomen were seated on either side of a middle-aged man. He was dressed well, like a businessman, pudgy and red-faced from alcohol. The three of them playfully touched and flirted, laughing loudly and often. One of the women eventually snuck a kiss on the man’s lips, which he seemed to enjoy. The bar was mostly thinned out by then. Dipasupil was long gone.
One day in March I met up with Dipasupil again, at a photo shoot she was doing for the TV show Extra in Midtown. The shoot went fine—the segment had been on the Duggar family, who have 19 kids, and Dipasupil had commanded it well. She skirted around efficiently to get what she needed, weaving around cameramen, climbing up and down a step ladder, even at one point calmly and authoritatively directing the group together so she could shoot everyone in one frame. But afterwards Dipasupil was still a bit depressed. The previous week her ex-wife, who has full custody of the two kids, had informed her she would only be able to see them every other weekend from now on, instead of every weekend as she had been. Dipasupil understood this, she said. She understood what Catherine was trying to do, that she wanted to wean the boys off the idea that things are still like they were before and that their dad is still a regular part of their lives. She gets the logic. But it still hurt.
Losing her kids, Dipasupil said, has actually been the hardest part. A few weeks before, when I had met her at the same Chelsea restaurant and asked her if she had any regrets, Dipasupil was adamant that she didn’t. She gets the question a lot, she said.
“And I could list a lot of things that people would think would be my regrets. Yeah, I lost my career. I lost my family. I lost this, I lost that. And my life is more difficult than it would have been if I hadn’t done all of this. But I can honestly say I don’t have any regrets. I’m very happy with who I am today, where I came from. I’m not ashamed of my past life.”
Except maybe for the boys.
“They still call me daddy,” Dipasupil explained then, letting out a flurry of laughter. “If we’re out they usually call me Dia. But at home, the six-year-old—he’s very cute, very affectionate—he’ll say things like ‘Oh you look very pretty today’—he’ll call me Dia. The 11-year-old—he has a more difficult time with it. He insists that he still call me Daddy. I said, ‘That’s ok, you can call me whatever you want. I’ll always be your daddy. You can’t change that—I’m your dad. My life is different now—I’m a different person than when you were born.’ But I will always be their dad.”
When she started talking about her kids Dipasupil had pulled out her iPad, to show me one of her favorite pictures. It’s the two boys, up close in the frame. Both look like their father, with dark black hair, dark eyes, soft features. Marcus, the older one, has his arm tight around his younger brother, holding him close, and both are looking straight ahead, smiling softly. Then Dipasupil glanced down at the picture one more time, a picture she must have seen a thousand times, and beamed.
*This name has been changed
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