"The day my boyfriend told me he wanted to be a woman."

Image via iStock.

I believed sexuality was fluid and love knows no gender. I was wrong.

On our first OKCupid-initiated date, Ryan* and I timidly gazed at each other across a cafe table, punctuating the silence with sips of lattes. But by the time the discussion escalated to our common childhood spiritual obsessions, it was as if we’d known each other forever.

As we got to know each other over the next few weeks — our Scrabble strategies, our opinions on Lady Gaga’s merit as an LGBT icon, and even the darkest revenge fantasies we’d ever had — the awkward silences evaporated.

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We spent our dates laughing through inconsequential debates like “What does it mean to have your cake and eat it, too?” (He somehow got through 19 years thinking it meant “to serve dual purposes, the way cake is both food and decoration.”)

During one of our outings, a homeless man asked Ryan for a sandwich and he bought him two.

Less than a month passed before we said, “I love you,” and the ensuing spring was a whirlwind of covert hand-holding at parties, waking up to roses on my windowsill, five-minute breakups followed by poetic apology notes, and everything else involved with being 20 years old and in love for the very first time.

But one aspect of our relationship was not typical — and was not something I’d signed up for.

Ryan had always told me he felt uncomfortable in the male gender role. At the time, I was reading feminist and queer theory, participating in a discussion group about transgender rights, and gaining awareness of how our society’s definition of masculinity harms both men and women. A macho man wasn’t for me.

But as time went on, Ryan began dropping hints that his discomfort was more deep-seated than I originally understood. When I’d ask what he was going to do about that, he’d say, “I don’t know,” and I’d get worried, so eventually he dropped it.

In my mind, it was no longer an issue. But in his mind, a seed had been planted that was growing larger each day.

One afternoon I got a call from Ryan while I was at the gym. He said he had to see me. Thinking this was one of his romantic surprises, I rushed off the elliptical, back to my dorm, and into his arms. But I didn't get the welcoming embrace I was accustomed to.

"We need to talk."

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"Are you breaking up with me?"

"We're completely different people."

"But you love me."

"No, I don't anymore."

The rest of that spring semester was the worst period of my life.

Every morning, I woke up praying that the inexplicable breakup was just a terrible nightmare. Every waking moment was filled with an ethics lecture on which I wanted his opinion, or a talking dog video I wanted to show him, or a flower shop where I once got him a tulip after a fight because they were his favorite flower.

In early June, I sent Ryan a card for his birthday explaining how much our relationship meant to me. I hoped this letter would give me closure, along with the physical distance between us as I traveled to Italy to study abroad that summer.

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But shortly after arriving, I received a Facebook message from Ryan with the following explanation:

"I was always an open book with you. But there was one thing I never was able to be as honest as I wanted about. Since I was very young, I felt uncomfortable living as a male. I would ride my bike to Walmart to buy girls' clothing. I felt so ashamed and confused about why I did this. (Post continues after gallery.)

"When I was a freshman in high school, I saw a documentary about transgender people. It clicked to me that I was transgender. My parents freaked out and tried to convince me it was a phase. I sunk into a severe depression. In order to just be normal, I acted masculine.

"I broke up with you because those feelings were coming back up. I cared about you too much to tell you the truth at the time. I hope you understand that I need to transition to live a happy life and that I do and always will love you. I gave you all of myself when we were together and will continue to do that as long as you allow me."

As I read and reread this last paragraph, the cloud that had been hanging above me over the past few months lifted. The breakup wasn't my fault. He hadn't stopped loving me.

I was finally waking up from the nightmare. I called Ryan and immediately suggested we get back together.

The impending transition was an afterthought. We'd cross that bridge when we got there, I figured. After all, I believed sexuality was fluid and love knows no gender. And our love, if anyone's, could conquer anything.

But we got to that bridge sooner than I expected.

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We argued on Skype every few nights about Ryan's transition. I pulled intellectual arguments out of gender theory books to try to dissuade him from going through with the identity change or hormone treatments (he wasn't planning to get surgery).

I cited scholar Janice Raymond's assertion that "a female mind in a male body only makes sense as a concept in a society that accepts the reality of both." The very goal of making his body or mode of dress "match" his personality, I said, validated gender norms.

Why couldn't he just be a feminine man?

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I understood that I couldn't intellectualise away someone's deep-seated identity. But I was afraid of losing him. To what, exactly, I wasn't sure.

I'd seen documentaries about people undergoing gender transitions, and they always reassured their friends and family that they would be the same person. But I felt like someone else was about to replace my boyfriend. I felt cheated out of the person I fell in love with.

Even when we tried to talk about other things, Ryan's gender identity was the elephant in the room. I'd constantly beg for reassurance that he wouldn't break up with me over it again.

He'd send me messages like: "I'm worried that I'll put a lot into this relationship right now and when you get home you will realise what I want to do and not want to be with me."

The truth is, I didn't fully grasp what the transition would mean. I had tunnel vision clouded by my fear of losing the most precious person in my life.

But when I got home that August, it did get more real.

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First, there were little things like wearing nail polish. "I can handle that," I thought. "I know cis men who do that."

The next step was wearing women's underwear, which was his way of feeling more like himself without fear of public judgment. (It was unclear what pronoun Ryan preferred to go by. Ryan still presented as a man to most people, but out of necessity, rather than preference. And he preferred the label "genderqueer" over "man" or "woman.")

That was when I started to feel viscerally repelled.

This repulsion brought me face-to-face with my own socialisation. Whether or not sexual orientation is innate, as the "born this way" argument would suggest, I doubt there's a gene for preferring masculine clothing. After all, I knew from my studies that associations between gender and fashion were culturally specific and arbitrary.

I hated myself for letting these arbitrary associations make me averse to my own boyfriend's self-expression.

I was an instrument of the gender stereotypes I detested, and they were hurting my relationship.

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Still, I wasn't going to give up the love of my life over a few pairs of panties, so I reminded myself he was the same person underneath and got used to it.

When Ryan started to buy women's outfits, my distaste turned to panic. I pictured myself walking down the street with someone others would scornfully label a transvestite. I pictured everyone wondering what we were at family gatherings. I couldn't imagine how I would explain. I couldn't image how we would exist.

I wanted my boyfriend back instead of this stranger I'd never seen before. But Ryan reminded me that I was now getting more of the person I loved, referring to himself as Ryan 2.0. (Post continues after gallery)

The new-and-improved Ryan still made snide remarks about the religious right and listened to a baffling combination of gangster rap and country music, and bought lobsters just to set them free in the ocean.

More importantly, Ryan took more care than ever to remind me that he loved me with thoughtful gestures like making a collage of our love notes for my birthday and bringing me my favorite baked goods when I was stressed out with school.

During the rare moments when we were able to take our minds off Ryan's gender identity, I caught glimpses of the untainted relationship I was desperate to preserve.

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But more and more alarms interrupted these sweet dreams of how things used to be. Ryan started talking to doctors and therapists about going on hormones, which would cause him to develop wider hips and small breasts.

I wondered: Would this make me bisexual? Pansexual? I'd never been attracted to a woman before, but I couldn't imagine my attraction to Ryan suddenly disappearing. And he didn't want surgery, so our sex life wouldn't be too different.

I was braced to at least try to make it work, as I was with the clothing and makeup and everything else that went into the transition.

These changes were even more overwhelming for Ryan. On top of trying to figure out who he wanted to be and how to craft a life that would accommodate that person, Ryan had to deal with a partner whose desires conflicted with the person he was becoming.

Out of the blue one evening that September, Ryan sent me an uncharacteristically angry Facebook message calling me "f*cked up" and blocking my Facebook and my number. With no way to contact him I fell into a state of grief for another two months.

In November, Ryan unblocked me and sent me a message similar to the one from June admitting what I already suspected: "I broke up with you because I knew romantically we could never make it work with what I needed to do." Sadly, this was true.

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Even though I didn't want to be the one to end it, having that decision made for me was a relief.

The constant arguments and uncertainty about the future were causing us both more stress than the relationship was worth. And Ryan still had to sort out a lot of confusion about his identity and find a place to live, line of work and community that would allow for it.

As the dust settled over the course of the following year, we met up a few times as friends. Ryan was on hormones at that point but wore loose, gender-neutral clothing and looked pretty much like the boyfriend I once had. We reminisced about our relationship and agreed that our love for each other would outlast it, even if we lost touch.

We did lose touch over the years, as exes often do. So now, all my information about Ryan comes from Facebook.

At one point, she changed her name to something more feminine and her profile photo to one in makeup, earrings, and a homemade poster in the background quoting Lady Gaga: "Baby, you were born to be brave."

About a year after this personal rebranding, I was surprised to find that Ryan had switched back to his male name and a photo with a shaved head and masculine clothing. His Facebook wall now contains an amalgamation of Playboy photos, graphic anti-abortion campaigns, and statuses like "The friend-zone is the only place that has more deflated balls than a Patriots game."

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I don't understand. I don't try to.

But my best speculation is that Ryan hit the same wall I did when trying to envision his post-transition life, and bounced back in the opposite direction.

The wall I'm talking about is plastered together with our society's definitions of a man, a woman, a person, and a relationship. You've probably hit this wall, too, perhaps without recognizing it.

Women may have hit it when trying to assert their desires in relationships. Men may have hit it when trying to be emotionally vulnerable with their partners.

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And while it would be so easy to say I was just physically incapable of a romantic relationship with a self-identified woman, I find it more likely that this wall divided Ryan and I from each other and blocked my view of a future between us.

Even now, it's blocking my story from you, the reader, because the right words to describe Ryan and me and our relationship simply don't exist.

There's no word for someone who usually lives as a man but feels more like a woman, but really is neither or both or somewhere in between.

There's no word for the sexual orientation of someone who accidentally fell in love with a woman in the process of falling in love with a man. Instead, I'm forced to leave you with a muddled mix of he's and she's and no answers.

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I can only give you questions leading to more questions. I see in hindsight that there were other reasons the relationship didn't work out, including the immaturity reflected in Ryan's "f*cked up" message, and the ugly side now evident on his/her Facebook wall.

But if this weren't the case, would I have let gender confusion ruin an otherwise worthwhile relationship?

If I find myself in this situation again, will my increased comfort with gender nonconformity and decreased concern with others' opinions make the relationship easier? How can we tear down the wall that makes such relationships so difficult?

All I can say for sure is that I will always love him, her, or whomever Ryan turns out to be, not as my boyfriend or my girlfriend but as the person who was and still is my first love.