My name is Drew Riley, artist of the Gender Portraits series. Exploration is a self-portrait created as the second painting in a set of four self-portraits chronicling stages that I went through in transitioning. The series of self-portraits serve to tell more than my story, they also serve to talk about the journey of transition in general as it relates to the average transgender person of any gender.

The second stage that I’ve identified in my transition, which I call exploration, marks the journey of taking my newly formed identity out into the world. There is some overlap between the adolescent and exploration stages of my transition, as many of the larger adolescent questions about identity couldn’t be answered until I started trying to fit myself into social spaces more.

When alone, asking existential questions like, “Who am I?” seems insurmountably futile, but interacting with others automatically answers that same question through a series of small decisions. Over time, identity questions become simpler. I learned about myself by trying to get others to know me, and observing what I was showing them. Not consciously, of course, as this knowledge is based on hindsight.

More importantly, I needed to get away from the safety net of my friends. It was too easy to fall back into old habits with the people who had known me for a long time as the identity that I was trying to leave behind. I also instinctively avoided drastic experimentation around those whose opinions I cared about the most for fear of judgement.

The crucible for my transition came in the form of a series of costume parties over the course of a year. I had recently lost a number of friends due to moves, new jobs, new relationships, and I had just exited a relationship, as well. I was searching for something to occupy my time, and for people to connect with. I have a deep love of costuming, so when I heard about a group of people who hosted a circuit of costume parties a couple times a month, I was sold.

The nature of these parties allowed me to try on different “hats” around strangers. At this stage in transition, I was capable of presenting myself in cohesive, adult packages, but my identity was still young and chasing after stereotypes. Throughout my life there had been women that I deeply admired, and wanted to be like. I would try on their personas, seeing if anything fit.

Being single also meant that I needed to learn how to socialize in a romantic capacity. This was probably the single hardest obstacle I faced. Societal norms around flirtations and dating are extremely gendered, often more than anyone realizes. For example, as a man, I never had anyone walk up and outright complement my appearance with no other interaction or introduction. I never had someone buy me a drink, ask me to dance, or pursue me in any larger fashion. As a woman, when these things happened, I had no preparations to handle these situations. As someone who is only attracted to other women, the fact that these interactions came almost entirely from men added more complexity to the issue.

Women were another issue. I had only ever dated as a heterosexual male, and wouldn’t even call myself proficient at it. At that point in my life, I had a total of four relationships, including high school romances. Now, I was entering a queer space, faced with the task of communicating that I was interested in women, determining which women were attracted to female presenting masculine bodied people and which ones were interested in me. I also needed to be smooth and courtly about it.

I couldn’t interpret signals from other women properly. My female presentation usually made women categorize me as non-romantic, and they would treat me more familiarly and non-threateningly than they would have if I had presented masculinely. In addition, they were excited to bond with a transgender woman, and were trying to make me feel as accepted as possible. It was hard to tell if increased intimacy was a result of romantic interest, relaxed comfort or giddy enthusiasm. I was afraid to act on anything I thought might be romantic because I didn’t want to lose the friendship and trust that I had gained.

Many women also incorrectly assumed I was a gay man, dressing up to attract other men. To my dismay, there are a number of heterosexual women who brazenly flirt with gay men for fun, knowing that it won’t lead anywhere. All of these compounded issues led to a few awkward scenarios, and eventually made me give up on following romantic interests as a woman altogether. I had no compass, and decided that the consequences of incorrectly navigating these waters were worse than staying single for a while.

More than I imagined, gendered interactions permeate everything else in society, too. Admittedly, I occasionally amplified the social differences in my head due to my lack of a female experience, and too much self-consciousness. But in general, people treated me very differently, both as a feminine person and as a transgender person.

I also treated myself differently. I wanted so badly to succeed at being feminine that I lost my ability to act naturally. I was afraid to laugh because I didn’t want to bellow out a male chuckle, or squeak out a fake, feminine giggle. I didn’t want to tell passionate stories because I knew that when I get into the thrall of a tale, I start talking with my whole body and doing silly voices, all of which were very masculine. I often spent so much time thinking about how to respond to something, that by the time I settled on the appropriate response, the moment would have passed.

This led to me becoming very insecure and timid around social situations. As an ex-professional entertainer who prides herself in her extroverted nature and charisma, this was extremely upsetting. I often found myself getting ready for an event, imagining knocking everyone dead with my new look and whippy quips, only to find myself in the corner later that night racking my brain to figure out how to connect with someone, anyone. My contrasting expectations and reality only increased the discomfort of feeling lonely in a room full of people.

It was all so hard. Nothing felt natural. I was always thinking, and analyzing. I found myself relieved to return to daily life presenting as a man, to feel in control of my environment again, to relax. This made me question whether I knew what I wanted. I felt more comfortable socially as a man, except I didn’t feel like myself. As a woman, I felt like myself, until of course, I interacted with other people. Either way, I felt emotionally exhausted.

Luckily, I stuck with it. All I needed was time. Going out as glamorously as I wanted, in costume after costume, got a lot of fantasy fulfillment out of my system. I had nights where I was treated as a princess, a vixen, a rebellious hellcat, an artistic diva, and more. Once I proved to myself that those things were attainable, it was quickly apparent that they weren’t the thing that was missing for me to feel whole. My identity fell closer, and closer to home.

I was also meeting countless strangers, and engaging in small talk. Eventually, I got used to societal expectations. I learned which ones fit me, and which ones I was going to break. I learned how to be confident in myself again. Mostly, that involved letting go of fears. I rarely needed to change my way of acting, I just needed to learn how to be okay with acting like myself. I needed to see that people embraced me even if I wasn’t the perfect picture of a woman, whatever that is.

My biggest epiphanies came from women that I became close to, who had only known me as a trans woman. We bonded as fellow girls, and as a result they shared mutual concerns, and insecurities. These were people that I aspired to be like, that I felt embodied pure, unquestionable womanhood, and they were grappling with what it meant to be a woman, too.

Looking back, some of my favorite moments were from this stage in my transition. There were so many occasions where, for the first time, I felt like I made it. There was a lot of frustration and struggle, but that made the successes so much sweeter. There was also a lot of visible progress. I could see myself changing, and moving forward constantly. It felt very rewarding. In the later part of this stage, when I had found my confidence and swagger, I felt unbreakable.

As I finally settled into a state of security and acceptance, I started incorporating my identity into other aspects of my life. I started living more as a woman because I no longer needed to be a man to feel stability. As I started introducing my identity more completely into my world, I started realizing that there were a lot of practicalities of womanhood I hadn’t figured out, or even considered yet. And that led me to my next stage of transition.

More Stories