Skirting The Issues: Dating Revisited

Photo by A_Maslouskaya/
Photo by A_Maslouskaya/

Photo by A_Maslouskaya/

The last time I wrote about dating—in 2013, I believe—I lamented how exceedingly difficult it was to snag a date, let alone forge a real romantic relationship. Given that others told me I was relatively attractive, fairly intelligent, and even witty, I chalked up the drought to being transgender. Men and women (I’m bi, yep) my age (then mid-fifties) just weren’t willing to give me a thought.

I was certain that much of it had to do with a fear of being judged for being with me. Indeed, one man with whom I shared drinks and much laughter said as much at the end of our first (and only) date: “Ellie, I really like you but your voice is a problem.”

Recall that there’s an incongruity between my voice (still masculine) and my appearance (I’d like to think very feminine). What my date said in effect was, “I’d go home with you tonight but I’ll never introduce you to my adult children or best buddy.” In other words, if it becomes public that I’m dating you, someone’s going to think I’m queer.

I understood back then. It certainly hurt, but I wasn’t going to fault someone for not wanting to step out of their comfort zone. I wasn’t desperate for companionship and for the most part, I was (and remain) good with just me.

Fast forward to 2017. My how the landscape has changed! And on both sides of the equation.

On my side, I’ve now started a sixth decade of living. Never in a million years did I think that I’d want to date at such an “advanced age.” On the other hand, with age comes wisdom, a degree of self-confidence, and a willingness to push my personal boundaries. For me, that’s meant considering much younger people and maybe even entertaining a few things off the beaten path, so to speak. (That’s where I’ll draw the line on self-disclosure.)

Surprisingly, on the other side of today’s equation are way more people who are open to the idea of dating a woman who happens to be transgender. I’m talking men (at the moment, my gender of choice) as young as late-twenties and as old as early-sixties.

Then again, maybe I just crossed the line on self-disclosure.

So that there are no surprises for anyone, on all my profiles I’m very upfront about having transitioned genders. I also ensure that every potential suitor is aware of this; I’ve found that most men simply look at my picture without ever clicking on my profile.

Younger men really have no problem with my gender history. However, some older men don’t seem to quite understand the program. As one fiftyish man inquired, “So you were born a man?”

I responded, ”Yes, they got it wrong. It’s a deal-breaker for some but not all. If it freaks you out, I’ll understand.”

He came back with, “I don’t get it. Are you gay then?”

Me: “Nope. I’m actually bi but I’m sure that will freak you out too…It’s okay. Let’s just pass.”

At that point, I figured he would move on. Instead, he floored me with, “No, it’s kind of cool.”

Huh? Cool to be trans? From a gray-haired potential suitor?

For the record, I haven’t met this open-minded man yet, so I don’t really know if being “cool” counts for anything. Still, that he’s open to me really is something.

Thank god I’m getting to experience dating before I die. I mean that. I had been afraid that I’d never be able to do what any other women does—date, have sex, and possibly fall in love.

To what do I attribute this sea change in acceptance and openness?

A name: Caitlyn Jenner.

Say what you will about Caitlyn (and I do have much to say, not all of it favorable), she has near single-handedly transported transgender humans from society’s basement to at least its first floor. Her coming out in 2015 gave millions their first glimpse of what it means to be transgender; from there, many closeted trans persons (hundreds of thousands if not a few million) felt that they, too, could live authentically according to their true gender.

We’re talking somebody’s child or grandkid or the spouse of someone else, all coming out as trans or gender nonconforming.

That’s produced a cascading effect where today, nearly 30 percent of Americans know someone who’s trans. As that number grows, there will be even greater awareness and acceptance.

And more dates for trans men and women.

There’ll also be more pushback from religious and social conservatives, but that’s a topic for some other column.

For now, I’m just going to smile knowing that finally, I can get a date.

It’s a nice feeling for this sixty-year-old woman.

Ellen (Ellie) Krug is the author of Getting to Ellen: A Memoir about Love, Honesty and Gender Change (2013). She speaks and trains on diversity and inclusion topics; visit where you can also sign up for her newsletter. She welcomes your comments at [email protected].

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