The Best of Both Worlds

Avery Edison’s first dating experience after coming out as a transgender woman is promising until a slight miscommunication signals that everything is wrong.


Illustration by Elizabeth Simins for The Bygone Bureau

“It’s every bisexual’s dream! The best of both worlds,” she whispered into my ear as we watched a drag queen lip-sync to Katy Perry’s “California Gurls.” Julia had brought me to this Toronto gay bar promising an introduction to the city’s queer culture. I needed one: I’d been in town for three months and hadn’t even had a meaningful conversation with anyone from my end of the Kinsey scale, let alone spent the evening in a club full of them.

I’d envisioned slutting it up big-time when I moved to Canada for college. I still had a girlfriend back in Albany, New York (in fact, her parents were the ones funding my education), but she and I had an understanding: she knew that I’d spent my entire life feeling unattractive and unwanted, and I understood that she was kind enough to look past her jealousy and let me experience the dating world from the point of view of a gender I actually identified with.

So before I made the trip up north, I went to a salon and cut off the hair I’d been attempting to grow out ever since I announced to the world that I was a woman now. I printed out some JPEGs of asymmetrical haircuts and instructed my hairdresser to “dyke me up.” Surely some suitably gay hair would be all that was necessary to let the lesbians of Toronto know that I was on their wavelength and looking to get lucky? Well, no. Not quite.

Maybe Canada threw off my gaydar, maybe I didn’t know the proper flirting customs, or maybe it took more to shake off two decades of sexual awkwardness than a quick pass with some shears and a study visa in a commonwealth country — either way, I was having zero luck even talking to other girls, let alone dating them.

I should have been focusing on my studies, I know. I should have been appreciating my girlfriend, yes. I should have tried to get more comfortable in my own skin before trying to press it against other people, absolutely. But so much about my life changed when I came out as transgender — whole worlds of experience and fulfillment opened up to me. I found it easier to talk to friends, more satisfying to get praise for achievements, and less stressful spending time alone with my thoughts. I’d spent my entire life feeling like nobody could ever be attracted to the stupid boy-suit I was forced to wear, and I wanted to feel what it was like to have someone desire, on a visceral level, my body.

I was greedy. I still am. There are days (lots of them, to be frank) when the most gender affirming vibe I can feel from another person is “you’re not just a woman, you’re a fucking gorgeous woman, and I have to have you.” I know that’s shallow, but so much of the transgender experience is deep-level introspection and depression and wallowing in self-pity. Don’t I deserve something a little shallow?

Shallow like the way I approached Julia when I saw her trying to navigate our campus. She was short, and cute, and she had a nose piercing and — bingo! — an asymmetrical haircut. Not only did I feel like it was a solid indicator that she’d be down for dating someone on my end of the gender spectrum, but it also gave me an low-risk conversation topic once I’d exhausted the linguistic possibilities of pretending to help find the building she was looking for.

“So, I like your haircut.” Cue self-mocking laugh, pointing to my own ‘do.

She responded by making fun of her own hair, but saying complimentary things about mine. She said it looked soft, and asked to touch it. She took over the whole interaction, asking me why I was in Canada, what I was studying, and if I’d been to her favorite bar.

“Actually, don’t tell me. I’m taking you anyway. I could do with a hot date.” And there were the magic words. She thought I was hot, hot enough to go on a date. I felt giddy and proud to be objectified. Before things went any further, I filled her in on my open-relationship, and discovered that we had more in common than out haircuts: Julia had a boyfriend, but he was cool with her seeing ladies. So we made plans, and a few nights later we were watching “California Gurls” get the performance it deserved, and I questioned why drag queens were even a thing.

When she responded with that “best of both worlds” comment, I felt optimistic about our chances in the bedroom. Prior to that moment, I’d been trying to figure out how to tell Julia that I was a pre-operative transgender woman — that I still had a penis. I knew she was bisexual (she’d revealed that in our initial conversation, along with the fact that she had a boyfriend who was fine with her seeing other girls, plus a thousand other personal facts that I would’ve been too awkward to spill), but I was still worried that the weirdness of my gender status would put her off, regardless of sexuality. But this comment indicated that she was more than open to bodies that blurred the lines.

So I was not as worried as I usually am when, the next time we met up, I sat down with Julia in my dorm room and told her there was something she should know. Maybe the tone of my voice tipped her off, or maybe she’d just glimpsed my Adam’s apple a few too many times to not suspect, but she came right back at me with an offhand, “What, do you have a dick?”

“Well,” I replied, “that certainly makes things easier.”

I get nervous whenever I tell someone (especially someone I hope to be romantically involved with) that I’m a transwoman. My gender identity is hardly a secret (Google will even suggest it to you), but it’s still something that’s odd to talk about one-on-one. People don’t know how to react, and the conversation can get uncomfortable. But Julia knew exactly how she wanted to react: amazed, interested, and turned on. Barely a minute after I came out to her, she kissed me. Soon we were on my bed together.

And then she paused proceedings for a quick sidenote. “You know this means we can’t have sex, right?” I hadn’t been certain, but the possible specifics of her boyfriend’s “it’s fine if you date girls” rule had been niggling at me. Julia clarified that her dude was pretty territorial when it came to penetrative intercourse. As she put it: “No p-in-v for you and me.”

It’s weird, but the rhyme didn’t make the information any less upsetting. Because as much as Julia claimed that if I said I was a woman then that’s what I was to her, her boyfriend’s rule reduced me to nothing more than the body part I hate most. She may have thought I was the “best of both worlds,” but she wasn’t allowed to walk in one of them.

Of course, Julia isn’t the only person who’s used some variation of that dualistic phrase, not by far. I’ve come across more than one OkCupid profile expressing interest in transgender people as a chimeric mix of sexual characteristics. I’ve had a couple of friends express that my penis must make it easier for me as a lesbian, since it means I have all the fun of gay-identified sex with the added bonus of interlocking genitals. And, of course, vast swathes of the pornography industry sell the image of the “shemale,” a beautiful woman with a secret, whose implanted breasts you can feel against your back as she takes you from behind.

Ultimately, it all boils down to one thought: Yes, you can say you’re a woman, but your physical reality makes you something else. Something in-between.

Look, it’s not like I require the women I date to be cool with having my dick inside them. In fact, I’m fine if that never happens. But being shut off from the very idea of it, not even considering that having my penis inside you is different from having a man’s penis inside you? That hurts. It’s such tiny slight that I wish I could get over it, and not let it fester into something I feel the need to write an essay about, but apparently I can’t.

Now when I hear someone (especially a potential romantic interest) use a phrase like “the best of both worlds,” I see it as a red flag. As a sign that for all their intended openness, the person I’m speaking to still categorizes me as something other. Sometimes I just end the conversation there, sometimes I try to talk with them about how that’s maybe not the best language.

What did I do with Julia? How did I address my feelings? I wish I could say I was principled enough to stop making out with her, there-and-then, and discuss with her why I thought the blanket ban on my junk was upsetting. But I still so wrapped up in feeling sexy, in feeling wanted, that I mutely nodded and agreeing to the restriction. Later, after she’d left for class, I sat in bed and thought about this all for the first time. And I didn’t see her again. No matter which world I belonged to, I didn’t want her to be in it.

Avery Edison is a comedian and writer. She is just barely smart enough to include a link to her Twitter in this bio.