When Harry met Haley

In my Feminist and Gender theory class, as we discussed transgender issues, I brought in numerous representations of transgender and/or intersex, including such touchstones as Hedwig and the Angry Inch, TransAmerica, Orlando, and The Adventures of Priscilla, Queen of the Desert. As we discussed transgender, we started thinking that transgender was the most radical space for rethinking the relationship between bodies and gender, by making the body seem mutable and by underscoring a fissure between body and gender and between biology and gender. However, at the same time, we kept feeling that certain ways of talking about or imagining transgender led back to essentialism. The idea that one is "really" a woman inside or "a man trapped in a woman's body" seems to have some idea of what it means to be "really" a woman or a man, some sense of a gendered soul that seems to assume authenticity (as opposed to gender performance) and that assumes that nature makes mistakes (in giving the "wrong" body) rather than assume that gender is culture, not nature.

All of this became much more problematic when we looked at an Oprah episode (where else?) about raising a transgender child. What is curious in this segment (linked below) is that the 7 year old now-girl Haley, who was formerly a boy, Harry, never said to her parents "I want to be a girl." The parents, who describe themselves as progressive parents trying to raise gender neutral children, say instead that it was just "obvious." I am not sure what the exact process was -- whether they legally changed the child's name or whether her teachers know her story -- but there seems to be some secrecy attached to this, as Lisa Ling describes the family as "brave" for telling their story, suggesting that Haley's identity is now taken to be that of a girl in her community and that this show would be an outing of sorts. In any case, what bothers me is that these supposedly progressive parents could not imagine their boy, Harry, as a boy who could like painting his nails, wearing his hair long or playing with dolls and cuddlies. This, despite the fact that numerous parents tell stories of their sons doing exactly that -- as behaviors that they may or may not "grow out of." Instead, when he took on the gender neutral characteristics that they say they encouraged, they read him as a girl. In other words, they forced gender stereotypes onto him and decided that if he did such "feminine" things he must be a girl. I am not suggesting that there are not children who might feel a conflict between their inside feelings and outside body or that transgender is in actuality much more complicated and less rigid than many popular representations make it seem. But I am questioning the way in which transgender, in certain conceptions of it, allows us to re-map gender stereotypes and re-assert gender binaries, rather than explode those assumptions. So, my question is, why can't Harry be a cross-dressing nail painting boy? Why does wearing a dress and painting nails automatically make him a girl?
http://www.oprah.com/oprahshow/Barb-and-Steve-on-Raising-Hailey-Video