Isaac, age 17.Photo: Peter Hapak

Looking up from the changing table, the beautiful boy said to his mother, “I want to be a girl.”

This was not a passing phase. At 3, Mark asked to dress for Halloween as Dora the Explorer; his parents bargained him down to Darth Vader, which at least featured a cape. At 5, he insisted on trick-or-treating as Gabriella Montez, the High School Musical sweetheart. By then, his birthday parties were girl-only, with girl-only themes. Any boy toys received were instantly re-gifted to a cousin.

At first, his mom was “all Free to Be You and Me about it,” she says, willing to let Mark experiment within reason. But whose reason? The neighborhood’s? (The Benders, as I’ll call them, live in a conservative suburb in the tri-state area.) Their own? They of course loved Mark, the middle of their three sons, but worried that permission amounted to encouragement. As for Mark’s “reason”—well, as many people trying to be helpful pointed out, it was pre-rational, as if this diminished instead of intensified its authenticity. Who credits a child’s wishes? Their youngest son wanted to be Spider-Man.

But the Benders knew that Mark’s desire was different: It went far deeper than a costume donned or discarded. When asked to explain himself, he’d say things like, “I want to have long hair that moves.” The Benders would counter: Well, there’s the dad at the bus stop whose hair is like that, and he’s a boy; you can be a boy like that. “But I don’t want to be a boy with those things,” Mark would answer. “I want to be a girl with those things.” The more he pushed, the more they worried, and the more desperate his rhetoric became. “Why did God make me this way?” he cried. “I don’t like myself.” “I hate myself.” “I want God to take me up to the clouds and bring me back down as a girl.”

Through her reading on the subject, Mark’s mother gradually came to feel that she and her husband had to be that “God” for their son. But it took Mark’s implicit threats of self-harm to convince his dad. “I’m in a conservative business; I sell software,” he says. “I want the normal life. And this was gonna be different, when my son is getting out of the car in a dress in front of everybody. But then you have to think about who are you protecting? Yourself or your kid? People would say, ‘I can’t believe you’d let your kid do that. That’s abuse.’ I’ll tell you what’s abuse: suicide. Do you want a live daughter or a dead son?”

So the Benders, recognizing a tidal wave, stopped trying to hold it back, and instead tried to channel it. At the start, when Mark was in first grade, the result was what they sometimes call a “dual life,” or, more tellingly, a “half-life”: He was a “weekend and after-school” girl, tearing off his boy clothes the second he got home. But it soon became clear that this accommodation, which essentially told Mark he was “okay with us but not the world,” was untenable. Rules they erected to contain his feminine expression kept dissolving. At 6, Mark made a grand appearance at a pool party for his brother’s Little League team in a bikini. By his 7th birthday, the icing on his cake spelled MOLLY, and that’s who she has been in the two years since: “Molly 100 percent.”

Actually, “Mark” and “Molly” are the names Molly herself has chosen for use in this article, though she’d rather use the real ones; and though I am using male and female pronouns to differentiate between the time before and after the transition, her parents don’t. Out of respect for their daughter, they use “she,” or try to, even when talking about the past. Similarly, they have edited out of their albums and wall displays six years of pictures of Molly as a boy and have bought a new carved oak figurine to update the genders in a family crèche on the mantelpiece.

Molly, too, seems to have edited out any sign of her boy past. The lilac walls of her room are dominated by giant Hannah Montana decals. The closet and bureaus are jammed with pink clothes; a vanity overflows with costume jewelry, nail polish, and makeup. Even in a typical school outfit—a blue skirt over navy leggings, a blue top printed with silver peace signs that match the sparkly silver on her Twinkle Toes sneakers—she has located herself at the extreme girlie end of the style spectrum. And if this at first seems an exaggeration of gender iconography, her older brother’s room, down the hall, seems no less so, encrusted as it is with sports detritus, including a headboard made, by his father, of sawed-off hockey sticks.

Isaac, age 14.Photo: Courtesy of Isaac’s Family

At 9, Molly is bouncy, twirly, eager to chatter about everything she loves. You would never guess that she was until recently a very unhappy boy. The transition is not just ancient history but someone else’s history—something that happened to Mark, not Molly. Her brothers and friends barely blinked at the change, and her parents keep her as safe as possible from the nosiness and negative reactions of adults. (Some girls’ teams wouldn’t let her participate, so they sought new teams.) Molly’s biggest concern seems to be persuading her mother to straighten her “bumpy” chestnut-brown hair. Not that she’s deluded. She knows she’s still biologically a boy, and even seems, for the moment, comfortable enough to make jokes about it. “Whoops!” she laughed one day when she forgot what she was doing and ran past the big kitchen windows naked. Her father thought: Here’s my girl, my daughter, and she’s packing.

It’s a joke that lets an uncomfortable reality surface. However much the Benders have done for Molly, however difficult the decision that led to a so-far-so-good result, an even more controversial choice—one that tests the limits of what it means to be a supportive parent—awaits them a few years, or maybe just a few months, away.

Jean Malpas draws for me what a mother once drew for him: something she called a “gender cookie cutter.” It’s a blobby gingerbread person on which various currently understood components of gender are mapped. There’s biological gender, a matter of chromosomes and genitals, indicated with a circle around the gingerbread crotch. There’s gender style, sometimes called gender expression: a person’s preferred self-presentation in matters such as play and dress and gait and speech pattern. This has been indicated by a circle encompassing the whole body. Next there’s sexual orientation, or romantic attraction to others, assigned to the heart. And finally there’s gender identity, the innate sense of being male or female regardless of biology or style or sexual interest. For this, Malpas surprisingly circles the brain. Some theories now suggest that the prenatal environment renders the brain a “gendered” organ. In most people, brain gender ­matches biological gender. But not in kids like Molly.

Malpas, a psychotherapist in Manhattan who also directs the Gender and Family Project at the Ackerman Institute for the Family, runs a monthly support group for parents of kids on the transgender spectrum. (The Benders attend.) What such parents want is fairly uniform, he says: confirmation that they’re doing the right thing and support for common problems like what to tell the grandparents and whether to “let the girl go to communion in white pants instead of a white dress.” But the kids—who also meet at Ackerman, for a playgroup—are more various. Some need nothing more than the freedom to explore a preferred sense of personal style among others who won’t criticize it. Their nonconformity may be transient; many a boy who enjoys long hair and playing dress-up with tutus happily grows up seeing himself as a man, whether gay or straight.

For others, like Molly, the mismatch is direr and probably permanent. That does not mean it reflects a mental illness, though there is some debate among practitioners about how transgenderism, especially in youth and adolescence, should be categorized and addressed. For its upcoming revision, the Diagnostic and Statistical Manual of Mental Disorders is said to be reconfiguring its approach to the subject, focusing less on gender identity itself and more on the distress—or dysphoria—young people may feel as a result of it.

Regardless, Malpas is unambiguous. “Gender dysphoria in children is not a psychopathology,” he says. “And in the vast majority of cases it is not caused by other psychopathology, either. Nor is it generally caused by a particular family pattern, any more than gayness is caused by the old stereotype of controlling mother and passive father. It is just an essential part of who you are. Not that there aren’t any coexisting psychosocial issues. But the problems generally come from outside. If an 8-year-old girl has a really hard time in school because of her short hair and boyish clothes, and is bullied for that, that’s not her pathology—it’s the world’s.”

Still, youth transgenderism is a last frontier. Sexual orientation usually emerges with puberty; atypical gender style, in many families, is a nonissue whenever it arises. (Some parents may even express pride, and get competitive, about their kids’ cutting-edge sexuality or outlook.) But true transgenderism usually emerges very early, as it did with Molly, and is fiercely persistent. As such, it is exponentially more confusing to even the most gay-positive parents. Everyone has felt what it is to be sexually attracted to someone, so it’s not generally difficult to imagine what a gay child is talking about. But it takes a powerful act of imagination to understand what a transgender child, in his perfect little body on the changing table, might be feeling, or why he might become terrified as adolescence approaches. One father described the challenge of empathizing with his child’s fear this way: How would it feel if someone told him that one day soon he would start growing breasts and a vagina? “I’d try to stop that from happening,” he said.

Isaac, age 12.Photo: Courtesy of Isaac's Family

If the growing awareness of transgenderism and its early manifestation has meant that some families now support their children through the first steps of a transition, it has also made those steps more frightening, as parents realize sooner where the path is headed. The so-called social transition that allowed Mark to become Molly at 7 is just the beginning. The most widely used protocols for trans­gender health care suggest that “cross-­hormones”—testosterone for female-to-male transboys (FTMs); estrogen and progesterone for male-to-female transgirls (MTFs)—should be started at 16. This step is sometimes called the medical transition, beginning the process of reshaping the body chemically. Surgical transition, which creates the most obvious outward signs of the “target” gender by removing or creating breasts and genitals, is generally withheld until a child is 18, or otherwise of legal age to provide informed consent. (Many transgender people opt not to have such surgery at all, or to have certain procedures but not others.) Of course, by 18 or even 16, most transgender kids are already well along in adolescence, developing all the characteristics of the gender to which they are sure they do not belong. The ­medical and surgical interventions are in that sense too late, offering only a clumsy eraser against the powerful markings of maturity.

But within the last decade, endocrinologists have quietly been promoting another possibility. Since puberty itself is a torturous crisis for many transgender kids, why not use synthetic hormones called puberty blockers to prevent the problem altogether? When started at the right moment, these blockers freeze the child’s development before the arrival of noticeable ­secondary sex characteristics. For several years, perhaps as many as seven, they keep the child in a kind of preadolescent holding pattern, physically and even emotionally. Then, at 16, if a decision is made to proceed with cross-hormone therapy, the child will belatedly undergo adolescence—but in the desired gender instead of the dreaded one. MTFs will start to develop round hips and bigger breasts; FTMs, square shoulders and more prominent Adam’s apples. Later, if surgery ensues, there is much less of the wrong adulthood to undo.

These puberty blockers, more formally called gonadotropin-­releasing hormone analogs, are most effective if started when a child is entering Stage 2 of growth as indicated in the Tanner scale of physical development. At the beginning of Stage 2, there is almost no breast development in girls, or genital enlargement in boys, and only the faintest shadow of pubic hair in either sex. As Hanna Rosin reported in The Atlantic in 2008, girls reach Stage 2 at a mean age of about 11, boys at about 13. But those are means, and the age of puberty continues to drop. These days, Tanner Stage 2 may begin as young as 9 in both sexes.

Which suggests that if the Benders don’t want Molly’s male biology to assert itself any further, they may soon have to play God again, this time not just with swirly dresses but with the administration of years of hormones. That’s a lot of God to play.

The Benders are not alone in facing this decision, though statistics on transgender kids are hard to come by. Trans Youth Family Allies, or TYFA, a national support organization for parents, offers an anecdotal figure based on its counselors’ visits to schools: one or two out of 500 students. (Scaled up, that would suggest 150,000 to 300,000 nationally.) It’s unclear whether the phenomenon is on the increase, but it is definitely changing. Wylie C. Hembree, an endocrinologist affiliated with New York Presbyterian and a leader in the field, notes that MTFs, like Molly, used to be as much as ten times more prevalent than FTMs. Now the ratio is almost one to one.

Online, FTMs seem to be in the majority. YouTube is crawling with jerky homemade videos of transboys talking about transition. Their posts often include stark visuals of such rites of passage as the first injection of testosterone, the burning of uncomfortable chest binders, first sightings of facial scruff or biceps bumps, and, of course, the big reveal: the results of “top surgery,” or breast removal. By and large, the boys in these videos come off as thoughtful, funny, and unusually articulate. (A boy named Jacob reports the emergence of “a solar system” of acne and “gross, nasty” “bacne” after four months on “ ’stosterone”: “I gotta deal with it; it’s puberty, right?”) But in a few cases it’s hard to tell whether these FTMs are expressing relief and pride in a new, more congruent body or indulging in a kind of macho posturing that seems as conventional and false as the femininity they meant to escape.

Isaac, age 12.Photo: Courtesy of Isaac's Family

This is a major concern for some parents facing the decision. Frieda—as I’ll call her—is an 11-year-old biological girl who has always been very boyish, and who for the last two years has insisted on being called “he.” Frieda’s parents try to sidestep the fiat by forming awkward sentences like “Frieda will be over at six, and Frieda will bring Frieda’s bathing suit.” Despite resisting the male pronoun, they have no problem with Frieda’s preference for boys’ clothing, haircuts, and activities. If Frieda were a lesbian, her father says, “we’d embrace that, of course. That doesn’t push my buttons at all.”

But Frieda appears to be sailing in deeper waters. Though she’s fully knowledgeable about female physiology and development, she insists that she will not get her period; as proof, she points to other girls, like her sister, and says, “Am I like them?” To which her parents can only agree that she’s not. “Then I’m not a girl,” she concludes.

“And I don’t say, ‘Frieda, that’s impossible, you are a girl, it’s coming, get ready, deal with it,’ ” says her father. For the moment, his concerns are less about biology than philosophy. “The thing that does worry both me and my wife, as feminist parents,” he says, “is that we don’t want her developing bad ideas about being a girl. We want her to have pride in being a girl, and to know that a lot of great pro-girl stuff is happening.” The problem is that Frieda isn’t interested, and forcing the issue seems eerily similar to the social pressure that feminism is meant to counteract.

“Perhaps it’s cowardly of us not to intervene more forcefully,” says her father. (Frieda’s mother preferred not to be interviewed, and Frieda was off-limits.) “But we’ve elected to just go with it. When she and I are out together, she likes to go to the men’s room with me, and I let her. It doesn’t raise any eyebrows because she’s very boy-looking now. But that’s all going to change.”

For an 11-year-old girl, that change is fast approaching, and Frieda, despite her irrational certainty that she will never menstruate, got excited when her parents told her about puberty blockers. “Luckily, so far, she hasn’t said anything further about it,” her father says, “but I wish we hadn’t raised it” because he’s “adamantly opposed.” Partly, his objection is to turning what he sees as a personality trait into a medical issue. “I don’t want to mess with her chemistry. If she’s interested in changing herself physically when she’s 18, despite the fact that she might have to do some awful surgical interventions, that’s up to her. I don’t want to enable that now.”

Many parents feel the same way. Though they would not hesitate to treat their child with serious drugs for a serious disease, they often see gender transition as frivolous or elective, and the blockers as mysterious, possibly destructive chemicals. In fact, they are synthetic versions of naturally occurring hormones, and have been used for decades to treat endometriosis in women and prostate cancer in men. Dr. Hembree tells parents that aside from the rare allergic response and the ­occasional hot flash, there are no adverse consequences, and that the puberty-­suppressing effect is completely reversible merely by ceasing treatment. To him, and to many parents for whom the blockers buy time to see how their child’s transgenderism develops or doesn’t, it’s a miracle treatment, albeit an expensive one; each monthly injection of Lupron, the most commonly used brand, costs about $600 in the United States, and is not always covered by ­insurance. A typical treatment lasting six or more years may add up to more than $50,000.

But for Frieda’s father, cost is not the issue, nor simply his distaste for medical mucking around. “I’m kind of a knee-jerk anti-­capitalist,” he says, “and I see this fetishism about taking dramatic decisions earlier and earlier as a bit like all the junk we get fed as parents to do better with the best toy and best therapy and personal coach. I guess my view is more like: Hey, let it ride. We all are in this world to struggle with a million things, and we don’t have to try some fancy new solution. Even if she said, ‘I really need this, I need to get rid of these breasts,’ I don’t know … I don’t think … I don’t see that as a solution for her crisis … not crisis, it’s not a crisis … for her exploration.”

He pauses after the struggle with that sentence and changes tack. “But it’s really cool territory she continues to explore. Personally I hope she does that in such a way that she doesn’t have to fuck with her body. If she started to be insistent, that would be interesting. But we’ll drive off that bridge when we come to it.”

Isaac, age 5.Photo: Courtesy of Isaac's Family

The problem is that they may be on the bridge already. Society tolerates tomboys far longer than sissies, a fact that can delay recognition of the underlying difficulties facing potential FTMs whose transgenderism persists as puberty approaches. At that point the cover offered to the world and to the child by jeans or short hair or baseball caps suddenly stops working.

For Isaac, whose parents agreed that he could use his real first name for this article, the crisis came as no surprise. Highly self-aware, articulate, and (thanks to the Internet) better informed than his parents, he’d for years been a passionate advocate for his own view of gender roles. “Around 6, I just started getting pissed at girls who wore pink,” he says. “Why are you doing that to yourself?

Even though Isaac (then known by a girl’s name he prefers not to discuss) expressed a wish to grow a beard at age 10 and to dress as Jughead or a bloody corpse at Halloween, his parents, both downtown artists, thought their child was just “gender­queer,” and were proud of it. It wasn’t until camp the summer after sixth grade that they realized how fast things were moving: They dropped off a daughter at the beginning of the session and picked up a son at the end. In fact, the transition happened on day one. “I’d been to the same school since I was 2 and never had a blank slate,” Isaac says, and even though his mom and therapist advised that he wait until fall to make any changes, “I couldn’t stop myself.” He introduced himself as a boy, wore only the boxy boys’ clothing he’d brought, and swam in boys’ trunks in the lake. (Most of the girls in Isaac’s cabin accepted him as such—it was, after all, a performing-arts camp.) He was delighted, but his parents were stunned: Their daughter had disappeared.

But that’s not how Isaac saw it. That same year, he posted a video online ­consisting of stills of himself as a long-haired redhead in cute dresses gradually giving way to a crop-mopped urchin in a Brooks Brothers suit. The video, set to mournful alt-rock music, is called “There Once Was a Little Girl (Who Never Existed).”

Having forced the social transition at camp, Isaac insisted on returning to his Manhattan ­private school that fall as a boy. The school, blindsided, did not respond well. Isaac was made to sit in front of his seventh-grade class and explain himself to his peers, without any adult backup, feeling like he could not refuse to answer their intimate questions. (When asked “How do you hide your boobs?” he pulled an Ace bandage from his backpack and said, “I use this to bind my chest.”) He lost all his friends. “There was not one phone call for any birthday party or playdate for two years,” says his mother. Still, Isaac persisted, putting up with teachers’ insistence on grouping him with girls and petitioning the administration to be allowed to make a presentation to the school on November 20, the Transgender Day of Remembrance. (He was turned down.) “In the end, it was good for me to deal with that,” he says. “It was a hump to get over to express my gender in the way I wanted to.”

Persistence is a crucial feature of the transgenderism diagnosis, and a procedural quandary as well. One of the reasons many parents reject the idea of puberty blockers is that the evidence of persistence is equivocal. Some studies report that less than a quarter of prepubertal children diagnosed with gender dysphoria become transgender adults, but these numbers count anyone who leaves the study or does not elect to have surgery as nonpersistent. Even so, for many parents, the odds of their child continuing to identify as transgender are too low to justify a medical intervention, though of course a child is not an average of other children, and the point of the hormones is to buy time to sort things out. For kids like Isaac, whose transgender consciousness began early on and only intensified in adolescence, there may not be much to sort. They rarely revert.

Isaac’s parents certainly understood that he wasn’t kidding: “Who would stick with this transition in the face of such social pain if it weren’t true?” his mother says. But the puberty blockers he soon began campaigning for freaked her out. “I instinctually didn’t want to start messing with Isaac’s endocrine system. I said no.” As she recalls this, she looks tortured with guilt.

Despite Isaac’s pleas and arguments, supported by the advice of “every medical and psychiatric professional” his parents took him to see that fall, they waited. “It didn’t make sense to me,” he says. Tension in the family rose. By spring, when he was turning 13, and well past Tanner Stage 2, Isaac was terrified of the “super-feminine puberty horrors” that might start at any moment: “the period, of course, and the breasts. I was a ticking clock.”

“You have to understand that a ton was happening so fast that year,” says his mother. “So much pressure. We were still struggling with the pronouns! To decide your fate on top of that—”

“But it wasn’t my fate!” Isaac interjects.

“We didn’t feel that way. And what if it was only a phase?”

“But the effect of the blockers is reversible!”

“We didn’t understand that clearly.”

Assertively but not angrily, Isaac drives home the point. “For me it was sort of a win-win situation, a good way to hold things off until either you want to start testosterone or you decide you want to express your gender in other ways. The fact that my parents weren’t allowing it was completely devastating. I thought: Why are they being so stupid and cruel? As if you’d never eaten ice cream and then you’re told all about it but you can’t have it.”

His mother can only say, “He was 13.”

In the end, his parents relented after Isaac, on a visit to his grandmother, called them from the bathroom, wailing. He was having his first period.

A boy bleeding, even if you know the boy is biologically a girl, is a long way from the philosophical conundrums that make it easy for outsiders to mock trans people. The byzantine nomenclature devised by partisans—including titles like “Mx.” as an alternative to “Mr.” and “Ms.,” and the use of “they” or “zie” or “hir” as pronouns to replace “he” and “she”—suddenly seems beside the point. What such diversions mask is the intensity of the pain involved when a person’s deepest idea of himself is betrayed by his body and found insupportable by his society. When Isaac’s parents finally saw through the abstractions of gender politics to their actual child, they rushed into action.

Just before leaving for another season at camp, Isaac took his first dose of Lupron. “I chose a pill form,” he says. “I should probably have started injections, which have a stronger effect, but I don’t like shots. I should have manned up.”

The blockers quickly stopped the periods, but too much breast development had already occurred. When Isaac had his top surgery last summer in San Francisco—some California doctors will perform the operation sooner than the recommended age of 18—he needed a full mastectomy instead of the simpler “keyhole” surgery that would otherwise have sufficed. The result was a longer recuperation, much larger scars, and a chest that may never look quite normal. Isaac has made his peace with that, and is just happy, between the surgery and the testosterone he started at 15, to see more of a man when he looks in the mirror. He has grown taller, his voice has deepened, and his body shape has begun to alter as muscles and fat rearrange themselves in a more typical male pattern. On a recent video he shows off his leg and facial hair, which, though sparse, is good enough for him.

The testosterone also initiated the emotional maturation that the puberty blockers had delayed. He finally had his first crush at 15. Now, at 17, he is less volatile than he was as a preteen, and the anxieties that plagued his childhood (he was terrified of fire drills) have mostly dissipated. The person he wants to be is no longer just an imaginary being but someone others can see when they look at him. Really, that’s all they can see. At a new school, the group of girls he quickly fell in with treats him as a boy; they asked him to manage their roller-derby team. In some cases, their parents—he grins to say it—won’t let him sleep over.

If the drama of transition isn’t complete, it’s at least quiescent; his latest videos are often about things like choosing colleges to apply to. His initial gender overcompensation has relaxed into a more idiosyncratic expression of self. Big assertive hand gestures are undercut with ironic eyebrows, and a careful self-monitoring makes sure that phrases like “it takes a lot of balls” get revised to “it takes a lot of guts.” However boyish he looks, he seems to have landed in an interestingly indeterminate place. “I act as a fairly effeminate male a lot of the time,” he says. “I’m giggly, I have no interest in sports. I’m not the most masculine transperson. But I’m a guy.”

His parents are relieved to feel they eventually did the right thing. His father was “proud and very quickly got used to the pleasure of having a son”: a “shirtless boy” parading around the house. Like Isaac’s mother, he has incorporated imagery of Isaac in his artwork, in his case a short, sweet film. Her response seems more ambivalent. The paintings she’s done dwell on the scars. She takes photos of them and gouges them by hand, then blows them up, silk-screens them, and mounts them on wood panels. It’s as if she’s reliving what she allowed.

Kim Pearson, executive director of TYFA, says she has a Ph.D. in “previously had daughter.” After seeing the movie Transamerica in June 2006, her 14-year-old girl came out to her as transgender, presented a list of to-dos she’d researched on the Internet, and at once began her transition to Shawn. Pearson wishes she had known what was going on in time to give her “fabulous” son the advantage of puberty blockers, but it was too late. Instead she got him a prescription for testosterone, earlier than protocols usually suggest. The decision may have saved his life. “I later asked him, ‘Had we not gotten it, how much time do you think you had?’ He answered, ‘Six months, top.’ ”

Although TYFA focuses on a hopeful message for parents of transgender kids, and suggests that they will one day celebrate the “journey” their child is taking them on, suicide is the dark energy behind the group’s efforts. (The child of another of its three founders killed himself at 16.) “Trans kids are the highest suicide risk on the planet, bar none,” says Pearson. Not because of their transgenderism per se but because of the reaction, real or anticipated, they feel the truth will elicit if exposed. And so, though she understands how parents can be so afraid of making a mistake that they’d rather do nothing at all, Pearson encourages them to act fast. Especially with an adolescent, they may not have time to get comfortable with a medical intervention, or to leave the decision until adulthood. “That’s assuming your child lives to 18.”

But when a child is still a child, still in the single-digit haze that parents like to assume is sexless and even genderless, with no rebellions or acne or sapling mustaches to spoil the illusion, the risk-benefit analysis may seem more ambiguous. A 10-year-old I’ll call Nick, who was born a girl but has been living as a boy for several years already, appears to be a happy, well-adjusted kid. Pleasingly androgynous and typically chaotic, he’s faced few external problems, perhaps because his parents work hard at supporting his identity while keeping their confusions to themselves. His sister, just 7, accepts him without reserve.

Still, some things make them wonder. When Nick was 4, a newborn brother died without ever making it home from the hospital. Not immediately, but soon thereafter, “the transgender thing started to happen,” says his mother. First it was I like boy things, then I’m a tomboy, then I wish I was a boy, and eventually, by second grade, I am a boy. “So one of our first thoughts was that this was a psychological way of replacing a boy in our family. Of soothing our grief.” She pauses. “But you could think back to anyone’s childhood and ask: Did this make me that? At a certain point the why doesn’t matter.”

Nick’s parents are not quite sure they’re at that point. Are his air-guitar slashes and karate kicks just typical boyishness, they wonder, or an expression of something unsettled? “He wrestles with it daily,” his father says. “The inner frustration that comes with being in the wrong body. And as a result he has moments of deep, deep anger, to the point we’ve had incidents with him punching other kids.” He looks at his wife sheepishly. “And the guidance counselor once.”

“Yes, but this guidance counselor had kicked him out of the boys’ bathroom unfairly,” she quickly adds. “A whole bunch of boys were in there fooling around and she only kicked him out.”

Their ambivalence is almost physical, and everything they say seems to recapitulate the struggle they have gone through to find the right loving way to look at their son. “We’re following Nick’s lead but,” says his father, and that’s the complete sentence. The prospect of using puberty blockers only intensifies their uncertainty. On the one hand they resent that most endocrinologists, following the protocol, require a child to complete a year of therapy before receiving treatment. “Honestly,” says his mother, “you can tattoo a third of your body or get double-D boobs without therapy. Why do you have to prove yourself to get hormones?”

On the other hand, they admit to the usual resistance, if for an unusual reason. “I was thinking that my child at least has to have the grounding in the fact that she is a biological girl,” says Nick’s father. “That we’ll love and accept her in whatever form she wants to express that, but there’s no moving forward without a basis in biological fact. I didn’t want to be validating a pretend life. And then, too, you feel like doing that shouldn’t be in your control. Do we sign the paper that stops puberty for our child, which is a natural biological process? It’s a godlike thing. A wrong godlike thing.”

The result of their misgivings is that ­after an initial consultation with Dr. ­Hembree several months ago, Nick’s parents have “dragged their feet” on getting the bone scan needed to help determine his Tanner stage. “We were supposed to have a follow-up visit after six weeks,” says his mother, “which I totally blew off.” She frets for a moment. “I need to do this ASAP.”

At this point Nick and his sister arrive home from school. The two share a bedroom along with an avalanche of books, toys, games, and clothing. Near Nick’s bed, in a tank, sits a bearded dragon, motionless. “It’s my prize possession,” Nick volunteers. When I ask if it’s a boy or a girl, he says there’s no way to tell.

Often called brave, kids like Nick, Molly, Frieda, and Isaac don’t see themselves that way. To them, what they are trying to do is as natural a shift, if a much more complex one, as stepping from shade into sun on a cold day. You move to your comfort. Still, parents see it differently, knowing what the world, with its violent transphobia, has in store; they cannot afford to take their children’s nonchalance at face value. Kids really don’t know what they’re doing or saying except, uncannily, when they do.

So yes, it’s astonishing how dauntlessly they choose to endure painful medical procedures and stare down the liberal perplexities of their families. But what actually seems bravest, to an outsider, is how they do these things more or less alone. And what seems scariest, to a parent, is the way that aloneness suggests how little we know about any child. Transgenderism may be the last, thinnest edge of the wedge of liberation, but it’s also the most piercing. The concept it threatens is even more fundamental than race and orientation and physical ability. Or so we’ve thought.

Which makes for the uncomfortable realization that sophisticated, pushing-the-envelope parents are not necessarily the ones who are most helpful to their pushing-the-envelope-even-further kids. “My recent observation,” says Isaac’s mom, “is that when you’re in these progressive cultures it can be harder to see that your kid is trans because you’re so steeped in this epic of gender freedom. It’s fluid, it’s great, one thing one day, another thing the next. You start applying that as a fantasy of an ideal on top of someone who might really need to be helped in a very specific way, and you can end up doing harm. It’s not all about freedom.”

Meanwhile, the Benders are ready. Unless something changes in Molly’s outlook, they fully expect to start her on puberty blockers when their doctor says it’s time. Otherwise, her mother feels, they would be “violating her rights as a human being to have an authentic childhood and to be an authentic person in this world and to live the way she’s comfortable.”

But Isaac, who now thinks of himself as “trans” rather than simply male, has lately been mulling the subject more critically. In a recent video called The Hypocrisy of Transition, he seems to be searching, from a “social-justice stance”—and as a way of avoiding his biology homework—for a clear space beyond questions of freedom and comfort. If, as he argues, there’s no inherent correlation between sex and gender, between body and self, why did he go through all this trouble to make the two “match”? What does “match” even mean? If he knows he’s a boy, why does it matter what his body says?

Because, he concludes, like everyone else, he’s a “societal person”: He inhabits a culture that believes in such things. He doesn’t make the rules. Nor, as strong as he is, can he live completely without them.