Everybody wanna see you with your hair down

Wanna hear you hit the high note

Wanna know what they can you get for a little less, girl

I don't

I know

Had the stones to fly

Had some hard goodbyes

Call me up, day or night

Free drinks and bad advice

- Dessa, "Dixon's Girl"

"The possibility was not flattering to me; it was terrifying. There were other things a guy could think I was, at he wouldn't be entirely wrong--nice, or loyal, or maybe interesting. Not that I was any of those things, but in certain situations, it was conceivable. But to be seen as pretty was to be fundamentally misunderstood. First of all, I wasn't pretty, and on top of that I didn't take care of myself like a pretty girl did; I wasn't even one of those unpretty girls who passes as pretty through effort and association. If a guy believed my value to lie in my looks, it meant either that he'd somehow been misled and would eventually be disappointed, or that he had very low standards."

- Curtis Sittenfeld, Prep

When I was a sophomore in high school, my school's quiz bowl team frequently crossed paths at area tournaments with the players from Sterling. Their captain was a short-haired, serious South Asian girl who was quick to answer all questions in a gruff monotone. That year, I usually played for the varsity "B" team, and we were coached by a former player with a reputation for drinking and swearing a lot and generally not giving a fuck. (Needless to say, quiz bowl was a lot of fun that year.) He jokingly referred to the Sterling captain as "Man-Woman," which was always good for a laugh when we played them.

The other night, I idly decided to skim the Illinois quiz bowl Facebook group I made as a freshman in college and through some minor stalking efforts made a discovery: that girl is now a man. She actually was transgendered; now he has made the transition, and is hopefully happier for it.

I've only met personally three transgendered people in my life, all within the last year. It's still a little jarring for me. And this case is especially so, for natural reasons: it's someone I knew in high school, pre-transition and before I had any real awareness of anyone being trans, much less someone my age. There is something that fascinates me about changing genders, and about the knowledge that there are people who feel profoundly wrong in their own bodies. It makes me want to keep looking, keep asking questions.

I have never seriously struggled with my own gender identity or sexuality. But most of what I know about gender theory comes from Judith Butler and her idea of performativity, that (in a very simplistic summary) binary oppositions of gender are not biological but conditioned and performed. In that context, I've definitely had an awkward relationship with the performance of my own gender. On the one hand, I was never a "tomboy" as a child. My sister, with her short haircut, love of sports and martial arts, and tendency to climb anything that could possibly be climbed, fit that role perfectly. I'm not athletic at all, and I'd definitely choose Barbies over baseball as a child, but I was never exactly "girly." I still don't wear makeup except for parties and going out (and I haven't even done that for a few months). I remember my friends taking me to a clothing store and trying to force me to try on dresses, and me stubbornly refusing. The times when I did dress or act particularly feminine in my younger years were always anomalies. For example, cheerleading for my elementary school's basketball team one year: I had fun, but even just a year or two later, friends and teachers expressed skepticism that I'd ever done such a thing. And in truth, I only tried out for the cheerleading squad after trying and failing to make the then-co-ed basketball team.

I think complicating this relationship to gender has been my tendency and my desire, for almost as long as I can remember, to be different. I always had to make myself stand out in some way, or to show I was above the people around me. To show that I was too smart for their silly pleasures. It was that impulse that made me check out a book on philosophy from the library and read it conspicuously at Christian day camp the summer before eighth grade. That made me refuse to buy a dress for the eighth-grade dance--I just went in my plain school clothes. That made me wear my dad's authentic Scottish kilt to school one day freshman year of high school. And it's that impulse, too, that sometimes makes me feel guilty for loving "chick flicks" like You've Got Mail, while at the same time not feeling feminine enough or something when I revel in a Sam Raimi horror movie.

Of course, these gender distinctions are just simplistic stereotypes. There's an infinite number of ways to be a woman or to be a man. And I really am comfortable in my own skin--and it doesn't hurt, problematic as this may be, to have my body validated by male attention. But sometimes being around women my own age still makes me feel inadequate. I'm almost two months into my magazine internship, and I still feel a little awkward around the three other interns, all about my age, who share my work space. They talk about waiting for engagement rings from their boyfriends, take breaks together to go grab coffee (which I don't drink), ooh and aah over designer accessories online and each other's fashionable clothes. And the thing is, we get along fine--they're all likable and funny and love to read and write like I do, and every so often someone will forward a funny blog post or photo to the rest of us and we'll all crack up. But somehow feeling that I'm not poised and fashionable and effortlessly feminine like the rest of them keeps me feeling like I'm on the outside.

If there's anyone to be "blamed" for my unease with certain trappings of womanhood, it's probably my role models. My mother, of course--she's always been extremely low-maintenance and unconcerned with her clothes or hair. She never showed me how to put on makeup or taught me what various accessories and pieces of clothing are called or gave me a family recipe or even helped me figure out tampons.

And I can probably chalk some of it up to my closest friends. Most of them are just as low-maintenance as I am (if not more so), and even once some of them began to wear makeup and nice clothes and attract boys, our conversations were always more about classes and books and movies and music and religion and politics than about those "girly" things. And again, I think it has to do with this idea--borne of our personalities and our "Gifted" education--that we should be above such things. I remember this sort of struggle I had with a few of my friends in seventh grade, where I would try to bring up boys and which ones we all "liked" and they would evade the question. We had always spent a lot of time making up goofy fantasies and games and stories, and it was a lot of fun. But I felt like we were growing up and I was starting to really notice our male classmates, and I couldn't get them to acknowledge that. And it frustrated me--I remember venting about it one day to my mom and sobbing that, while I loved my friends, I didn't feel as if I could actually talk to them.

It's the same with my sister--she had the same mother as I did, after all, and as I said she was always a tomboy. In the last few years, we've opened up a lot more about having crushes on actors and musicians and occasionally coworkers, and we'll compliment each other's clothes or hair. But it's still tentative. We still retreat quickly into our familiar and wonderful world of inside jokes and funny anecdotes and privately mocking people we know and reminiscing about our childhood.

But am I supposed to blame the people I love most for not feeling like I perform well as a woman? Of course not. It would be stupid to want to trade love and acceptance and stimulating conversation and thousands of belly laughs for the ability to braid hair and put on eyeliner. And if confiding crushes and learning about makeup weren't part of my friendships, then neither were catty gossip and overblown drama and fallings-out.

Tomorrow is Halloween, and so most people are celebrating tonight because it's Saturday. Tonight I will put on a skirt and blouse and lipstick and heels and attempt to style my hair so that I look like Mad Men's Peggy Olson, one of my favorite female characters on TV. Tonight I will perform, but I will also drink and hug and dance and laugh and reside in the love of my role models.