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I Dated A Trans Guy In College — Why Do You Ask?

I wonder if I should’ve asked Greg more questions, perhaps not about his transitioning, but about his feelings.

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Words frequently escape me. They buzz around my head, just out of reach, and I struggle to snatch them and catalogue them into something coherent and meaningful. I had never talked to Greg before, and when he instant messaged me, back in the days when instant messaging was still a thing, I stared at my computer screen for too long, uncertain of what to say. I only knew him as the cute guy who sat four rows down from me in design class, the sweet dude with a deep Southern voice that made me woozy whenever he raised his hand and asked the professor a question. Greg had a confidence with language that I lacked. Words seemed to run away from me, but they flowed from his lips like molasses, smooth and rich and sweet. I could almost hear his voice as I read the words on my screen:

"Hey, Adam."

My fingers hovered above my keyboard, the blue light of my computer casting long, spindly shadows underneath them, and I struggled to think of the perfect nonchalant response. Whatever my reply was, it sufficed. We spent the rest of the period talking to each other, and it quickly became the routine, the professor's lesson falling on deaf ears.

A week later, Greg asked me out and I said yes. I performed the pre-date ritual of plugging his name into Facebook and scouring his profile for information that might aid me. It was disappointingly sparse, but there was a wealth of photos for me to pore over and scrutinize. He was smiling in every one of them, perfect white teeth. When I happened across a photo of him standing up in a canoe, clad in nothing but red swim trunks, I felt a stab of jealousy about his sculpted abs, thinking nothing of the two large half-moon scars on his chest, his slight waist, those slender fingers gripping a wooden paddle.

We dated for several weeks, though I hesitate to even call it dating. We were both 20 — kids, really — and neither of us had an appetite for anything serious. On our third or fourth date, when Greg told me he had been born a girl, the reveal was so casual I wasn't sure I completely heard him at first. At that point I'd formed a habit of only half-listening to Greg, content to simply languish in his syrupy drawl. I knew what he was saying was important, though, so I sat up a little straighter. I thought, I'm supposed to ask questions now, but I couldn't think of anything to ask so I just said, "Oh."

After a moment of silence, Greg said, "What do you think of that?"

"I mean...nothing?" I replied. "I don't know, should I?"

Greg shrugged, and that was the end of it. I had questions, but none of them seemed appropriate. How much did the surgery cost? What was your name before? How did you manage to grow such a nice beard?

We never really talked about Greg's transition, partly because it never felt like there was a need to, but also because I felt like I shouldn't. I wasn't sure if he'd be open to discussing that part of his life, so I kept my questions to myself. Greg's appearance was convincing enough that nobody seemed to wonder about his life before. I rarely thought about it. We could walk down the street together without a passing glance, two men the same as any other. Even when we were alone in the dark, our bodies tangled and connected, it felt normal and natural.

We drifted from each other as summer approached. I saw him less and less around campus, and after a while I stopped seeing him entirely and assumed he transferred. Those early college years were filled with so many transitory relationships — friends, boyfriends, girlfriends, affairs I still can't summon labels for — and Greg become a sort of fond footnote in all of it.

In recent years, as conversations on transgender issues become increasingly prominent, I think about Greg more and more. I don't feel confident about terminology and the politics, so I mostly keep quiet. I read articles. I listen to people who are smarter than me. It feels safer to stay quiet, but then that's not really an option either. People are dying because others stay silent. I wonder if I should've asked Greg more questions, perhaps not about his transitioning, but about his feelings. I wonder where he is. I wonder if he's alive.

Because I feel so inadequate on the issues, I rarely bring up Greg, even when a conversation might naturally lead to it. I'm not always sure how to speak on issues regarding the G and the B in LGBT, let alone the T, and I question what right I have to do so. The chorus of knowledgeable voices is humbling, and I can't help but feel my small voice would become lost and unnecessary. When I do mention Greg, the responses I get are baffling at best, offensive at worst.

"That's so weird. What did it feel like?"

"That's brave of you."

"I'm jealous. Fucking a tranny is on my bucket list."


It's been coded in me to keep quiet about the relationship, that I'm supposed to be ashamed of it. It feels so strange, since the relationship seemed so simple, so uncomplicated and sweet. It's difficult to talk about my time with Greg without feeling like I'm bragging or trying to make a point that I'm not sure I'm entitled to. I suppose words still escape me, hazy and fleeting. I wish I could see Greg again, because I have a lot of questions — but then again, I wonder if I'd even want to ask them. I might hear his voice and simply be happy to listen.

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