Jason Cole

What’s it like to be a man who became a woman—and now identifies as neither? The genderqueer revolution, from the inside out

Jason Cole is a modern-day Mr. Dressup who keeps an entire wardrobe of flamboyant outfits in a single suitcase. Every morning, Cole, a 33-year-old school administrator, reaches into the Tickle Trunk, searching for a new outfit. Inside are tie-dyed rainbow jeggings, leather short shorts, T-shirt dresses and yoga pants. There are kimonos, glittery belts and sheer tights. A leather mankini from Toronto’s World Pride is stowed away, along with flannel button-downs and a “Boys Club” tee. “I flip back and forth, masculine to feminine,” Cole says, with a dramatic wave of the hand. Standing at five feet, 11 inches, Cole is comfortable showing off a thick beard while wearing a flowing gown, or donning tights with a biker jacket. Even Cole’s voice is a gender bender, zigzagging between a flowery Valley girl purr and a no-bullshit roar.

Cole identifies as genderqueer, a term for people who see themselves not as male or female, but as somewhere in between. The term first appeared in 1995 in the radical queer newsletter In Your Face. “The fight against gender oppression,” wrote its editor, Riki Anne Wilchins, “is about all of us who are genderqueer…those of us whose gender expressions are so complex they haven’t even been named yet.” Twenty years later, rigid gender boundaries are dissolving, and the so-called genderqueer movement is inching into the mainstream: non-binary people are protected legally in Ontario under human rights legislation, and most queer community groups recognize them. In Australia, people can list their sex as male, female or X. Even young celebrities—Miley Cyrus, Ruby Rose—identify as gender fluid.

For some people, being genderqueer means embodying qualities that are both masculine and feminine. Others express neither, taking on a neutral, androgynous identity. Many take hormone treatments or undergo plastic surgery to shape their bodies in a way that reflects their self-image. The English language hasn’t caught up with the genderqueer movement—there’s no consensus on which pronouns to use. The most common choice is the singular “they” (this is also Cole’s preference), but it makes for confounding prose. Dozens of other options exist, including “ze” (which rhymes with “he”), “hu” (a shortened version of “human”) and “*E” (the asterisk is silent, like the symbol for Prince). None have permeated the mainstream, which makes writing about the subject challenging (I’ve chosen to sidestep pronouns entirely).

For years, Cole desperately sought an in-between space, a way to live outside the binaries of man and woman, gay and straight. Cole tried to cope with alcohol and drugs, with BDSM, with a transition to womanhood and a reversal back. Out of that chaos, a dynamic new selfhood emerged: neither male nor female. It turned out to be a release not just from the binds of gender, but from identity itself.

Jason Cole at age nine (third from left), pictured with sister Shannon (far left), and cousins Shane and Brittany; at Grade 8 graduation (Images: courtesy of Jason Cole)

Life was tumultuous from the start for Jason Cole, who was born in 1982 to a conservative family in Scarborough. Cole’s parents, Rick, a contractor, and Ruth, a welder, divorced when Jason was two. A few months after her divorce was final, Ruth married a man named Dave and, in 1987, moved her family to a semi-detached house in Brampton, where she had a daughter, Shannon, when Jason was seven.

Growing up, Cole fell in love with female pop singers—Janet Jackson, Whitney Houston, Mariah Carey—and spent every afternoon memorizing their dance moves. Once, in 1989, the seven-year-old gathered Ruth and Dave in the living room and played a cassette of Janet Jackson’s “Rhythm Nation.” Jason performed a dance routine to the song, all marching feet and flailing arms. “That’s great, sweetie,” Ruth responded, uneasy that her child was mimicking Janet Jackson instead of Michael.

In 1994, the night before Halloween, Jason and Ruth headed to the store and realized they’d left their costume-buying too late—all of the superhero getups were sold out, and Catwoman’s leotard was the only one left. It was slinky and form-fitting, and Jason convinced Ruth to buy it. When Jason wore it to school the next day, other kids were ruthless, shrieking “little girl” and pushing their classmate to the ground. Despite that experience, Jason continued to role-play as Catwoman behind closed doors.

In high school, Jason was equally attracted to men and women, but when a friend came out in Grade 11, Jason followed suit. Within a year, Cole met a man in his mid-30s in a chat room. There weren’t many other openly LGBTQ people in the suburbs, and the man told grand stories of life in the Village. It wasn’t long before Cole was spending every weekend downtown. One night, before they left for a Church Street bar, a friend slipped Cole a tab of ecstasy. “It felt like I was in a Dalí painting,” Cole remembers.

Cole kept using ecstasy, and was soon doing coke and ketamine, addictions that persisted on and off for the next decade. After high school, Cole enrolled at Fanshawe College in London, then dropped out before the end of the semester and couch-surfed for a few months, occasionally sleeping on a park bench as a last resort. Though Cole was still attracted to women, friends pressured the teen to push it aside. “Say you’re gay,” they urged, until Cole finally relented. “I was trapped in a gay box,” Cole recalls.

Two years later, Cole was seeing a man named Adam, and the couple moved from London to Toronto. At the Pride Parade in 2002, Cole wore a long, voluminous satin fuchsia gown and a blue bandana styled like Axl Rose. For the first time, Cole’s appearance blurred the lines between male and female, and it felt right. For weeks after the event, Cole wondered, What does this mean about me?

After a long night of partying in 2003, Cole crashed at the Croissant Tree coffee shop, which opened for the day at around 4 a.m., just as the clubs were serving last call. Cole sat crumpled on a chair in the corner of the café, grappling with the depression and splitting migraine that came with an ecstasy crash. Usually, the owners kicked Cole out, but this time they were preoccupied by Cassandra Do, an exuberant trans woman and sex worker, who was regaling everyone in earshot with stories about her life in the Village. She talked about making her own living, fighting poverty and forging independence. She wanted to get out of sex work eventually, hoping to save up enough money to go to nursing school. Do was the first transgender person Cole ever encountered—and she seemed infinitely happy. “I wanted to be just like her,” Cole recalls. They never had a chance to become friends. Later that year, police found Do dead in her bathtub. She’d been strangled by one of her johns. Following Do’s death, Cole mustered the courage to begin dressing more feminine, wearing tights and crop tops. Do’s memory gave Cole new resolve.

Within eight months, Cole landed an office gig at the Toronto District School Board, and later began working as an administrative assistant at a downtown high school, answering phones and filing papers. By 2008, Cole and Adam had married. But the steady job and relationship masked Cole’s emotional wounds instead of healing them. The partying and substance abuse persisted—Cole treated hangovers with aspirin and covered up booze breath with mints. Bubbling beneath Cole’s confidence was a profound sense of sadness. My body isn’t right, Cole would think.

Cole and Adam ended their relationship in 2010. Cole spent the next few years trying to stay sober and relapsing frequently, guzzling white wine before and after work. Sexually, Cole was diving deeper into BDSM encounters, once enduring 189 canings from a partner (a tattoo on Cole’s arm commemorates the occasion). Eventually, in the summer of 2014, Cole sought out a psychiatrist at Mount Sinai Hospital, where the doctor concluded that Cole had bipolar disorder, and prescribed valproic acid and lithium. After the first dose, Cole experienced complete calm. “I’d never felt better in my entire life,” Cole says.

The drugs helped clear Cole’s mind. In the months that followed, Cole began spending time with a group of trans activists, and those long-buried questions of gender resurfaced. I don’t see myself in men, Cole thought. Their masculine identities seemed foreign. Cole dreamed of softer skin, curves, broad hips and long legs. After years of denial, the truth finally became clear: this wasn’t a gay thing or a bipolar thing. Cole simply wanted to be a woman.

On a sticky day in August 2015, Cole went to H&M and bought a dress: a $20 knee-length polyester shift printed with kaleidoscopic squares and triangles, cinched at the waist with a gold belt. Back at home, Cole slipped into the dress and applied a thick coat of mascara. It was a moment of complete comfort. Cole decided to transition as quickly as possible, and within a few days had made an appointment with a nurse practitioner at the Health Centre at 410, a clinic at St. Michael’s Hospital. That was September 1, 2015, the day Cole’s Facebook name changed from Jason to Maya, inspired by Maya Angelou. Five days later, Cole uploaded a YouTube video reciting her famous poem: “The caged bird sings / with a fearful trill / of things unknown / but longed for still.”

In the H&M dress that convinced Cole to transition; in one of several wigs purchased as Maya; out in the city as Maya (Images: courtesy of Jason Cole)

Cole’s first order of business as Maya was to buy a wig: a bubblegum-pink bob. Bangs framed the face of someone familiar but unrecognizable: Cole was transforming from the inside out. Cole applied eyeliner and rosy lipstick, and strutted down the sidewalk, daring passersby to stare. More wigs soon followed. There was a long chestnut version with bangs. Another was cropped and maroon. Still, it was the party wig—pink, bright, luxurious—that made Cole feel truly beautiful.

Coming out as trans was easy for an extrovert like Cole.“There’s nothing I can say that can shock my family anymore.” Cole broke the news to Adam with a cheeky wink. “Your ex-husband is about to become your ex-wife,” Cole said with a laugh.

Cole began taking the hormone suppressant spironolactone and a regimen of estrogen, obtaining the drugs from the nurse practitioner at 410. “It was intense,” Cole recalls. “Being a woman is hard.” Cole would experience symptoms similar to severe PMS, swinging from sad to angry to sexually frustrated. The physical results were pleasing, at first. Facial hair slowed its growth, chest muscles became less pronounced, skin softened. Cole was also on the Ontario wait list for sexual reassignment surgery to receive a vaginoplasty. There were other options too, like tracheal shaving, to reduce the appearance of an Adam’s apple; laryngeal surgeries, to change vocal pitch; and facial feminization, a series of augmentations to soften the cheekbones, jaw and nose.

As Cole proceeded with the transition, however, second thoughts seeped in. On the street, passersby would shout “fag” and “hey girlfriend.” One evening, after exiting a downtown subway station, a man solicited Cole for sex. “I’ll pay for it,” he begged. “How much?” Cole simply ignored him and walked away.

The worst discrimination occurred at work, at a new school placement in North York. On the second day of the school year, a man refused to deal with Cole regarding his daughter. “I don’t want to speak to that faggot,” he screamed. “That’s not even a person.” The incident prompted Cole to take a leave of absence from work. “I was scared for my safety,” Cole says.

That leave triggered a period of unhappiness. “Maya” started to seem like another temporary solution to Cole’s ongoing identity crisis. Appearance-wise, being Maya was fun: the women’s clothes fit snugly; the wigs were a nice way to spice up an outfit. But Cole missed masculinity and the sense of security that came with a male appearance. Sexually, Cole had been in a drought. “I was celibate for three months. That’s like, eons for me,” Cole says. “I truly thought no one could love me. I wasn’t happy as Maya.”

Cole had been trying to stay sober during the transition but turned back to the bottle while visiting a group of friends who lived in Chicago. When the others went home after a night out, Cole ordered a shot of vodka. One drink quickly turned into a dozen. A few hours later, Cole left the bar, drunk and despondent, made a pit stop at McDonald’s for a last meal, then headed back to a friend’s house to drink more vodka. Staggering into the kitchen, Cole grabbed a butter knife. Cole’s left forearm bore the brunt of a clumsy, drunken suicide attempt that included feverishly sawing away in the hopes of hitting an artery.

Within a few minutes, Cole regretted the decision. Faint and frantic, Cole rushed to a friend’s bedside and woke him up, explaining that they needed to go to the hospital right away. The friend wrapped Cole in a blanket and called a cab. Once they arrived at the hospital, nurses took Cole’s vitals and bandaged the arm. Then an ambulance whisked Cole away to a facility for 24-hour mental health care.

Cole spent the next 10 days at the John J. Madden Mental Health Centre, a state-run facility in Chicago. The room was white and sterile, a single hospital bed taking up most of the space. The window was bolted shut and the door locked from the outside so patients couldn’t escape. “It wasn’t jail, but it wasn’t the best,” Cole says. The staff suggested that Cole present as male during the hospital stay—they were worried that transphobic patients might lash out. Cole agreed, left Maya’s wigs and clothes at a friend’s place, and answered to Jason for the next 10 days. The only concessions to Cole’s female identity were a dull razor to shave away the stubble and a daily dose of estrogen (along with the usual bipolar cocktail). Cole had gone from man to woman to something in between.

The switch gave Cole a chance to contemplate. There was no pressure to behave within the confines of one gender or the other. It took Cole’s favourite aspects of manhood and womanhood and swirled them in a blender. The feminine clothes, without the restrictive female pronouns. The soft skin, without the name that didn’t seem to fit. The sexual machismo Cole embraced as a man, without the limits of an unfulfilled sex life, as experienced by Maya. If only I could live this way forever, Cole thought.

Life as a man had been unbearable, trapping Cole in a world that expected strength and machismo. But after three months of living as Maya, Cole realized that life as a woman wasn’t the answer either. There was too much pressure to present as hyper-feminine on days when Cole felt masculine, to throw on a dress and lipstick in place of biker boots and flannels. There was pressure for Cole to adhere to what society deems feminine, to endure the PMS-like symptoms that presented themselves again and again. Cole missed the camaraderie of fellow gay men and the choice to wear not what was expected but what felt right.

Cole remembered that first conversation with the nurse practitioner at the 410. “You can make this transition whatever you want it to be,” she had said. This transition should never have been about becoming a woman, Cole realized. Rather, it should be about finding an identity that fits—and that identity didn’t have to be male or female.

“It’s so rare for people to regret a transition,” says Jordan Zaitzow, the program co-ordinator at Rainbow Health Ontario, an organization that promotes health services for LGBTQ people. “But for many people coming to terms with a non-binary identity, it’s part of their process.” When one gender doesn’t fit, it is natural to try the other.

After 10 days in the mental health centre and a psychiatric evaluation, Cole was released. Breathing hard, bathed in sunlight, Cole felt the fresh air biting against bare cheeks—ready to live not as a he or she, but as a they.

Genderqueer identities have existed for generations, albeit with different names. Some Indigenous cultures define them as two-spirited. In South Asia, people who have transitioned are called hijra—it’s an official third gender in Pakistan and Bangladesh. And in Albania, “sworn virgins” refer to those born in female bodies who decide to live their lives socially as men and physically as women.

Now, in a post–Caitlyn Jenner world, non-binary people have a wealth of resources and language available to them. The gender queer umbrella covers dozens of identities, ranging from those without gender (agender) to those who feel disconnected from their identities (demigender) to those whose gender changes over time (pangender). Some classify non-binary genders as types of transgender identities. (This is a point of contention among many genderqueer individuals, who feel the term “transgender” only describes those who move from male to female or vice versa.)

Last year, the gender-neutral honorific “Mx.”—replacing Mr. or Ms.—was added to the Oxford English Dictionary, and the American Dialect Society named the singular pronoun “they” its word of the year. “New expressions of gender identity have generated a great deal of discussion, and the singular they has become a particularly significant element of that conversation,” said Ben Zimmer, a linguist and chair of the ADS’s New Words Committee. “While many novel gender-neutral pronouns have been proposed, ‘they’ has the advantage of already being part of the language.” On Facebook, Canadians now have 58 gender options to pick from—and if they don’t fit into any, there’s a blank space to type their own. And in Toronto, LGBTQ organizations like the 519 Community Centre and Toronto Pride host events for genderqueer Torontonians to congregate.

Some people don’t buy the notion of genderqueerness—many detractors think it’s manufactured drama, or confusion, or bullshit. Walt Heyer, author of Paper Genders: Pulling the Mask Off the Transgender Phenomenon, calls non-binary identities a “coping mechanism,” and suggests Cole’s self-identification isn’t going to last. “It’s a temporary holding pattern,” he says. Cole insists genderqueerness isn’t a choice, or a cry for attention. It just is.

Cole stopped taking estrogen the day after arriving home from Chicago. The beard was back within two weeks, and it quickly became a staple, a marker of Cole’s masculinity, paired with feminine dresses or tights. “We all have female and male qualities” Cole says. “How we choose to represent them is up to us.” For Cole, that means a short haircut paired with bright red lipstick, or playing a feminine, submissive role in the bedroom while wearing a macho leather outfit. Cole still loves to wear some of Maya’s clothes (kimono wrap sweaters, sparkly belts), and Cole’s passionate side—one that creeps up when attending activist rallies or writing blog posts—is inherently feminine. Cole is sensitive and emotional in a way that pre-transition Jason never was, yet Cole often embodies a male energy: strong, aggressive, alpha. Often, both the feminine and the masculine will blend together, creating a sort of yin-yang duality.

Cole no longer identifies as a man but still carries a nugget of male privilege: the full beard and thick build allow for easier assimilation with other cisgender men, potentially avoiding the discrimination Maya faced. When using the bathroom in public, Cole alternates between the men’s room and the women’s—whichever one feels most fitting for the day. And now Cole has a new group of friends: other genderqueer people. “We understand each other on a level that binary folk can’t,” Cole says. “We speak the same language.” Though Cole’s preferred pronoun is “they,” some old friends still use “he” out of comfort and convenience. “It’s only in the outside world, where people pass judgment on my identity, where that bothers me,” Cole says.

Every genderqueer experience is different. Lane Patriquin, a 21-year-old Toronto student who identifies as androgyne (a subset under the non-binary umbrella for those who don’t have male or female qualities), told me that using public washrooms can be a painful experience. “I’ve had people tell me I don’t belong in the women’s bathroom; I’ve had people tell me I don’t belong in the men’s bathroom. I get dirty looks wherever I go.” The discrimination has been so difficult that Patriquin doesn’t go out very often anymore. Another non-binary person I know, a 32-year-old artist who goes by the name Rain, feels uncomfortable filling in a biological sex on forms. “On job applications, for example, there’s only ever two boxes: male or female,” Rain says. “Gender is embedded in everything.”

Cole is more lenient. “It’s annoying to have my identity managed by strangers, sure,” Cole says. Yet, after years of bullying and harassment, these micro-aggressions seem to be a welcome change: “At the end of the day, who cares?”

One afternoon last February, I met Cole for coffee at the Croissant Tree. It looked different than Cole remembered: young regulars lingered in front of their MacBooks while scores of greying men sipped teas in leather armchairs. That day, Cole presented as more masculine, in a tight black sweater and a Blue Jays cap. “The last time I was here they kicked me out—nearly 10 years ago,” Cole said with a laugh that boomed across the bustling coffee shop.

When we met, things were going well for Cole, who hadn’t had a drink in five months. Cole joined the administrative team at a Parkdale elementary school in February, and recently moved back home to Ruth and Dave’s house in Brampton, hoping to save some money before embarking on a degree in English at York—even if that means stuffing more clothes into the Tickle Trunk. “I should probably stop buying so many clothes,” Cole admitted.

Cole’s exuberance and boisterousness—the laughs, the dramatic flourishes—reveal flickers of Cassandra Do: someone comfortable and self-possessed, with little care for the people who stare or the owners behind the counter. This is a happy medium, a space that is open, easy and free. There is no telling what Cole’s gender identity will look like in a few years, or a few weeks, or even tomorrow. And that is exactly how Cole wants it to be.