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Isaac, age 14.  

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.