My Best Guy Friend Became My Best Girlfriend

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My friend Juno and I both need to pee. Bad. As the movie credits roll, we shuffle out of the darkened theatre and book it to the restrooms. The men's entrance is on the left, women's on the right. This is the moment when we split and pivot towards our respective labels, like we've done at the countless bars and pit-stops that have peppered our eight-year friendship. But not tonight. For the first time, we go through the same door together.


Until he was 32-years-old, my best friend was a man. She's now a woman. And while she adjusts to this new reality, our relationship is shifting as we search for a new balance.

I met Alejandro by chance when I was eighteen, living in the student slums of Allston, Massachusetts. He was a laid back Colombian dude with a thick beard and welcoming smile and I instantly liked him. Our closeness grew through my early adult years. He cooked for me, helped me through a half a dozen apartment moves, and dated my close girlfriend. When I fucked up — jobs, relationships — or felt scared about the future, he'd say, "Don't worry about it! It's just life!"

In 2006, Alejandro moved to New York, built a recording studio and got a job doing sound at a club. But during the summer of 2009, Alejandro came for a visit and was almost unrecognizable. He'd lost 20 pounds and his face was gaunt. Over the next few days, he described to me his recent medical problems: how his hair was falling out, he was having erectile dysfunction, he'd been getting angry for no reason, and was severely fatigued.

Genetic testing revealed the cause: Alejandro, then 32, had Klinefelter syndrome. While males have an XY chromosome pattern and females have XX, Alejandro was born with an extra X, meaning he was XXY. He was, as some like to call it, intersex: a condition in which your gender cannot be simply defined as male or female, but is somewhere in the middle.

But what came as even more of a surprise to me was what he said next: The diagnosis confirmed something Alejandro had long felt. He wasn't comfortable as a man. It felt like a charade, fake, like he was acting, he said. He was never truly at ease.

I skipped out on work the next day to try and process what he was telling me. He didn't feel like a man? He had dated a good friend of mine for over two years! He wasn't sure what gender he was? My mind started obsessively running back through all the events of our friendship, trying to see if I could have — should have — recognized that he was unhappy.


Six months later, I visited Alejandro at his apartment in the West Village. At a bar, he explained to me that after extensive meetings with doctors and therapists, he had decided to take estrogen therapy. He now identified as a woman; her new name was Juno. And there it was: My guy friend was now my girl friend.

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Over the next year, we kept in touch over the phone and she came to Boston on work. Each visit brought more of a transition. Her face looked softer and more feminine. Her facial hair, thanks to electrolysis, was almost completely gone. Little budding breasts formed.

Juno's visits gave me little, quick, fascinating glimpses into her new life. But I didn't get to spend any extended time with her until November, when I got a job in New York and she said I could live with her in Queens.


I was moving in with my best friend — but I was also moving in with a stranger.

Her closets were stuffed with knee-high boots, skirts and cute shirts. Opening a cabinet door, I found an impressive nail polish collection. But although physically she looked totally different, the defining trait of our friendship — our ability to talk for hours about anything, hadn't fundamentally changed. If anything, we had so much more to discuss. Although I knew a fair amount about her childhood, growing up in Bogota, I absorbed it again, now through a different lens.



Juno's experience as a woman is so new. Over dinner and wine, we talk about what it means to identify as female. She tells me of the first time she experienced female jealously, felt the piercing glare from another girl, wracked with envy. She tells me about feeling a loss of personal space as a woman, of having to protect the area around her body in a way she never had to as a man.


It's not always easy. Sometimes, I mess up and say the wrong pronoun, simply out of habit. When we pop over to Duane Reade for snacks, or walk into a party, I'm often flooded with fears that someone will look at her too long, or make her feel uncomfortable. At a bar recently, a man got up and said, please, ladies, take a seat. Relief flooded over me. We are ladies, yes.

Small things are cause for concern. Putting a tampon wrapper in the trash, I think, if she sees this will it be painful for her? Is this a symbol of womanhood that she will never get to experience?


I find myself judging new friends on the look in their eyes when I tell them about Juno. I also question myself: Why do I feel the need to tell people the backstory? Am I trying to avoid awkward scenarios?

Our friendship is stronger than it has ever been. A barrier between us, subtle and invisible, slowly disintegrates as we get to know each other on a deeper level.


She tells me about feeling the power of being a woman, how the world can be gentler to you, people smile at you more, treat you kinder. She says physically, she feels more relaxed and engaged with her body. And when she dances, she says, it feels natural and unforced.

For the first time in her life, she feels truly connected to herself. And I too feel connected to her, as a friend, as a sister.


Melissa Jeltsen is a writer and recent transplant to New York City. Follow her on Twitter at @quasimado, where she tweets about politics and culture.



People are people so why should it be? you and I should get along so awfully! People are people so why should it beeeee? You and I should get along so aaaawfully!

(that's the only thing I can think of when I see "People are people")