Dear Abby and the Crossdresser’s Friend

Sigh… I’m going to show my age by recognizing I read the daily newspaper, The San Francisco Chronicle, and right next to the comics (Pearl Before Swine is my favorite) and the Challenger puzzle, is the Dear Abby column. There may be a web site for Dear Abby, look it up [here it is, here is the letter]. Dear Abby is like an incursion into the minds of ordinary people. So it should be no surprise that someone had an issue with a friend who is a crossdresser, but the whole letter from the friend in Tampa and Abby’s response were leaving me with the feeling that we have a lot of work to do to end the prejudice against trans people.

The letter is from the “best friend” of someone who just came out to him as a crossdresser, swearing him to secrecy. I already wonder how is the friend’s life to be crossdressing in secret for so many years, so secretly that even your best friend didn’t know about it. From the description it would seem the friend has discovered crossdressing when going through puberty, and I suppose that means it’s become more of a fetish than a way to express their gender. Yet I want to continue commenting about it because both friends seem to be homophobic and transphobic.

They explicitly say they’re not gay, as if this were extremely important to establish, but also as if crossdressing were a gay man’s thing. It’s true one sees it most often in gay circles, because the culture of drag makes it so visible, and many gay men have less fear of expressing themselves with nice clothes and manners. I personally have taken permission to wear dresses in a gay men’s circle because they were doing drag, but I quickly found a chasm in our intentions, theirs being to make a fun show, mine to discover my gender. The “not gay” understanding of the best friends, however, just reminded me of how some cisgendered men reacted to me if they had been attracted to my feminine semblance at first and “discovered” they might have been attracted to a man. Their facial expression shows anger, and it’s better to hope they aren’t the violent kind. I think of a young trans woman named Gwen Araujo who paid with her life in this situation. Why men become violent when they become aware of our existence, while they don’t seem to mind women they aren’t attracted to is hopefully the subject of someone’s graduate work at this time.

So I resented the “not gay” disclaimer in Tested in Tampa’s letter. It said both friends were so homophobic they had to make sure to reaffirm their sexuality in trying to open to each other. Maybe the crossdresser didn’t want to be killed by his “best friend” by swearing they were not to ever be attracted to each other.

But now the crossdresser friend who made it “sworn to secrecy” wanted to go out in the real world “as a couple?” How often had these best friends been out as not a couple? Had they never been together in one’s or the other’s living room in which it would be a lot easier to put a dress on and ask “how do you feel about it?” without the difficulties added by onlookers?

It’s true that this is a country, and a state (Florida), where one can be fired for being transgender. One can get killed for being transgender. It is entirely possible that the friend is transgender, and unable to safely express it. That is the point where I object to Abby’s response. She proposes to invite the writer’s girlfriend (first time I saw that mentioned that the writer had a girlfriend) along in the outing to make it clear the “best friends” weren’t out on a date. In other words, let the secrecy agreement go to hell, and open it to potentially murderous others (what if the girlfriend has a big brother who interprets it as the boyfriend being gay, as it seems to be the modus operandi there, and decides to beat them all up?).

Now I would like to hear about the friend. I wished they could find friends who not only understood, but embraced their personal exploration. I was lucky to have the safe environment of the gay men’s retreat to try putting a dress for the first time, and later to have friends in my house while I wore a skirt. I now wear a dress or a skirt on a daily basis, and I don’t care about passing. Passing has not only put pressure on me to spend interminable hours in front of a mirror, it has made it stressful to have things go wrong while out, and it has made me aware of the presence of transphobic men. When I don’t pass they just see me as weird and continue to scan the room for someone more attractive to them, whereas my true friends think I’m great as I am. Just as I don’t judge my friends’ appearances.

I think again about the friend. According to the letter, they have been crossdressing since age 12. A quick calculation tells me they would be about age 30 now. The letter doesn’t give enough detail about what they mean by “best friend.” They could be so homophobic that they never even spent a night in the same hotel room, which also means that they never talked their mind until the crossdressing disclosure.

And now I think of myself again. It is true that for so many years, all my friends had assigned me the default gender and sexuality. The “best” friends also thought it best to push me towards a life modeled after their own. It all came crashing after many years, and I was fortunate enough to find new friends who talk about possibilities instead of certainties. They welcomed every bit of my gender expression, adopted my new name faster than I could, and supported me when I perceived the world was against me. They were the pillars of my coming out to the rest of the world.

If I were Abby, I would have answered to support the friend or get out of the way. Maybe you can support your friend by accompanying them to a support group… You could wait outside or at a cafe nearby, but you would make it safe, because your friend is vulnerable. Also, if you could let go of your fears, accompanying your best friend out in their true gender is one of the greatest gifts you could give, because you can’t imagine how wonderful it is to be out in the real world, safe in your true gender. And if you do have a girlfriend who doesn’t understand it, maybe it’s time to question the “friend” in “girlfriend.”