THE BLOG
09/18/2014 11:23 am ET Updated Dec 06, 2017

Am I Transphobic?: My History With Transgender Women and Effeminate Men

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The question posed in the title is one I'd been putting off answering for months. It first popped into my head when Jared Leto won the Best Supporting Actor Oscar in February for playing a transgender woman in Dallas Buyer's Club, immediately making transgenderism a long-overdue topic du jour. But I wasn't ready yet: I considered it for about 30 minutes, and then I put it on the backburner.

Here's what I came up with during that half-hour of deliberation: I've never dated a transgender person, nor have I consciously pursued one. Does that make me not attracted to them, or have I just not met the right one? During my first year in Buenos Aires, I spent many late nights in an after-hours transgender club called Transformation. If I hooked up with anyone there, he was always a non-trans male (as far as I knew), though there was one drag queen-by-trade in men's street clothes. (Nobody ever would have guessed his night job by looking at him!)

The club's catered-to trans clientele (generally male-to-female) sometimes flirted with me, but generally half-jokingly, treating me mostly as a black curio. Had one of the ladies seriously made a move on me, would I have responded the way I've heard too many white guys respond to Asian and black men, with something along the lines of "I'm not into transgender people?" I may not be tacky enough to say that, but would merely thinking it make me any less discriminatory?

That's a lot to contemplate in the space of 30 minutes, but it wasn't my first brush with the social and sexual politics of gender identification. Years ago in New York City I had something of a "Lola" experience with a guy I'll call Justin. When Justin and I met at The Cock, my favorite gay bar in New York City during my final years there, he fogged up my vodka goggles: He was 6-foot-4, with a baby face and blond curls that made him look like a slender adult cherub.

After leaving the Cock and sobering up on carbs at Coffee Shop on Union Square West, we ended up at my place, which was two and a half blocks away. The next morning when I woke up, I looked over at sleeping beauty. Nice job!

Then I glanced around my bedroom and saw a bedazzled baby-blue t-shirt, a floral sarong and beige clogs on the floor. Blinking, I slowly turned back toward Justin and saw make-up smeared on the pillow. I'd noticed what he was wearing when we met, but thanks to the vodka, he might as well have been dressed like an all-American jock. By the time he was out of his sarong and baby tee, his attire had been a distant memory. It was all coming back to me.

I pushed his clothes under the bed and tried to forget about them again. When Justin woke up, we spent a couple of hours hanging out in bed, talking and listening to music. As much as I enjoyed his company, part of me just wanted to keep him out of his clothes for as long as I could because I didn't want to remember where the sarong fit in. But I couldn't put off the inevitable forever, and eventually, he announced that he had to leave and got dressed.

As we stood by the elevator outside of my apartment saying our goodbyes, I had mixed feelings. In running shoes, minus the sarong, he would have been perfect for me. I decided that it must have been a weekend thing, his Saturday-night attire, so I agreed to hang out with him again.

The following Wednesday when the doorman announced his arrival, I stood by my door holding my breath and praying: Please, let me see tennis shoes. When the elevator opened, the guy who stepped off was wearing a lavender blouse, white Capri pants, strappy heels and too much make-up. His mannerisms, which had been so neutral when he had been naked in my bed, were more animatedly feminine. His clothing was like Superman's cape. It seemed to turn him into a different person when he put it on, someone to whom I was no longer attracted.

The date went fine, but I couldn't stop wondering: What were people thinking about us -- about him. By the time our appetizers arrived, I'd decided our first official date would be our last one. It wasn't just about other people. I couldn't spend all our time together trying to get him into bed so he could tone down the feminine mannerisms and I could be into him again.

Although as far as I know, Justin's gender identity was male, I thought about him recently while watching an episode of Trisha that featured four transgender men. Watching the episode got me to see gender in a completely different light. Had I met three of those four guys on the street, it wouldn't have crossed my mind that they might have been born female. I probably would have dated one of them -- even after finding out about his birth gender!

Hearing their stories helped me to better understand my own reaction to masculinity and femininity and bring me closer to being able to face those questions that I'd been pushing to the backburner for months. I tend to gravitate more toward men in the 4-to-8 range on the scale of masculinity (with 1 being hyper-feminine and 10 being stereotypically macho), so even if a man who was born female falls into that range, I might still be attracted to him. Meanwhile, being into a feminine man isn't out of the question. I've dated 2s and 3s, though with the exception of Justin, none of them wore women's shoes. (For the record, I'd place myself in the 5 to 7 range, depending on the company I'm keeping.)

As far as transgender women, it's not the "transgender" to which I'm not attracted. It's the "women." I regard them pretty much the way I regard non-trans women. I'm generally not physically attracted to the female gender, even women who were born with male genitalia or ones who may still have them. Some people might call that discrimination. I'm inclined to call it being gay.

One of the transgender men on the episode of Trisha had a husband and four children. The husband was still with his wife-turned-husband, though, apparently mostly for the sake of the children. He said that while he was completely supportive of his wife's decision to transition, and they would always be best friends, their sexual relationship was over. He's not gay, and he's not attracted to men.

Despite "for better or for worse," he made perfect sense to me. Unconditional love doesn't necessarily include unconditional lust. If transgender people want to be respected and accepted for who they are, then the same courtesy must be extended to cisgender men. One's sexual gender preference deserves as much respect and acceptance as one's gender identity. This realization helped me come to terms with my general lack of attraction for trans women.

I'm still not sure what to do with my Justin experience, though. Attraction is generally more about how we see others than how they see themselves, so even if Justin's gender identity was male, when he was dressed, I saw so many feminine qualities on the surface that muddled my attraction to him. Sometimes I still wonder about him. Was dating a challenge because of how he dressed? How many other guys reacted the way I did? Were his sartorial choices merely a fashion statement or something more? Was he going through the initial stages of the transitioning process? I was too afraid to bring it up, preferring to act like it didn't matter. Did I fool him with my fake blasé attitude?

I don't know that I'd be any more likely to date Justin now than I was back then. My heart and my mind may be more open, but my attraction still isn't all-encompassing. I hope Justin eventually found someone for whom, unlike me, the strappy heels were a non-issue, someone who could appreciate him for who he was with his clothes on.