10/24/2013 06:13 pm ET Updated Feb 02, 2016

Are We Post-Sexuality Yet? My Date With a Straight Guy


Let me tell you a wee story.

I used to work for a gay organization in my hometown. Over the years, I would occasionally show my face at various events thrown by the organization, and it was there that I started noticing an adorable new male staffer. Every time I saw this person, we would strike up a conversation that was inordinately filled with smiles, and after the third or fourth of these exchanges, I made a mental note to ask him out. (Side note: I am rarely this much of a smooth operator. We just seemed to get along.)

After a few weeks, I finally emailed the staffer in question, and I'm going to go ahead and recopy the message here, because this will be rather salient later on.

Have you seen this show? Is it any good? If you haven't, would you care to be my date?? ... [Blah, blah, blah, office chatter.] ... Let me know -- been meaning to ask you out for ages actually.

The last line is especially important. I said I was asking him out. And the response I got was "yes." Long story short, because of scheduling conflicts, our plans to meet for the show never worked out, and then Pride weekend was upon us (he had plans, he said), so the whole thing died down. Slightly miffed, I was nonetheless ready to move on; it's not the end of the world when someone you're into just can't get it together to meet up.

Then, some weeks later, we had to reconnect on a work email, and suddenly I get a response from him saying, "When are we getting together?"

Which brings us to our date. Dinner. At a nice restaurant, my choice. I dressed up. He ordered wine. We started talking about... everything. "Where are you from?" "How's work?" Date stuff. About halfway through the appetizer, I heard something like, "When I moved here with my girlfriend...," and I just sort of nodded, thinking to myself, "OK, I guess we're saying that now, 'my girlfriend,' the way girls refer to each other." I even thought it was sort of cute. I only had eyes for him; I didn't check my phone, not once.

We were lingering, not rushing, and only decided to order a main course about an hour after we sat down. And that's when he laid it on me. Paraphrased, it went something like this:

Him: "I'm straight. You know that, right?"

Me: "Wait. What?"

Him: "Yeah, I'm straight."

Me: [Pause.] "No, I had no idea."

Him: "I didn't mean to mislead you."

I can safely say that that last line was verbatim. I was floored. I was aware of a decision that had to be made: "Do I get up and leave?" I wondered. "Do I have that in me? Or do I just sit here and shrug this off, which feels just as impossible?"

I chose the latter... and sat wondering how I got myself into this mess in the first place. Was I somehow unclear in my motives? Yes, sure, I had assumed that this person was at least interested in the general ballpark of my gender. (Cue that antiquated catchphrase about how to assume is to make an ass out of u and me.) However, I met him in an environment where this assumption would be considered only natural, and more importantly, I was never given any indication otherwise.

He sat there, still attractive, with a slightly hesitant but mainly nonchalant smile on his face, as the awkward silence dipped further into cringe-worthy territory. I kept the conversation going for at least another hour, but there were definite moments when the disconnect, how differently each of us had approached this evening, became too much for me and I lost focus. I walked him to the train (he was carrying a flimsy canvas tote and wore bright-red Tom's shoes) and kissed him on the cheek as he said, "We should do this again sometime!"

And suddenly, a twisted, alternative reality dawned on me: Could this person possibly have had the best intentions at heart? Did this kid, who, I was surprised to learn, was only in his early-ish 20s (he looks older), consider himself way more evolved than most? Ahead of the curve? Did he somehow think that he could "handle" this situation as just two friends, two co-workers, finding some off time to shoot the breeze? I am all for that, all for networking, totally and completely, except... I had asked him out. On a date. In no uncertain terms. And he was the one who actually made it happen.

I'm all for blurring the lines and allowing sexuality to be nebulous; I don't expect everyone to have their dance card filled out at all times with a check mark next to "gay" or "straight." But it must be said that as much as we'd all like to believe that our differences are nil, that we might soon live in a world where sexuality is entirely beside the point (like the proverbial "world without color"), boundaries will forever remain, to an extent, because there is still that uncomfortable part of the whole sexuality thing, the sex part, which a lot of outspoken voices in the LGBT arena keep mentioning is important not to brush under the rug. This is a necessary point, because if we continue to allow the nuts-and-bolts part of sexuality to be casually overlooked, bullshit like the above story may continue to happen.

Or maybe he just felt uncomfortable and didn't know what to do. I get that. As a gay man I know better than most how uncomfortable, inappropriate and out-of-place it feels to randomly mention your sexuality in a regular, day-to-day conversation (we call it "coming out"), but let's do the math: If someone asks you out on a date, and they are of the incompatible gender, then hey, mention it. Do your own coming out. This person had ample opportunity (in approximately 20 email exchanges) to stop misleading me, at the very least.

Last possible explanation: Could this simply have been an example of someone who didn't care enough to think about what his actions could lead to? Whatever the case may be, it's profoundly ironic that I hadn't felt this vulnerable, uncomfortable and out-of-place for being gay since I was in yeshiva high school. And this at the hands of someone who, last time I checked, was promoted to a leadership position in the gay organization for which I used to work.

The Epilogue

Folks, it gets worse. The preceding events happened well over a year ago, and I was so upset that I started writing the above blog post then. But I ultimately decided it best to just leave this icky situation alone and move on with my life. Apart from the most basic business exchanges, which have long since ended, my straight would-be beau and I never communicated again. Then, just recently, I was shocked and baffled to find an article, posted on a dating website, no less, in which the star interview was my former crush, and he was talking about our date!

This article is the definition of adding insult to injury, since it insinuates that I asked my former co-worker out under the pretense of networking or some such thing. (It should be said that this person had nothing to offer me professionally whatsoever.) The poorly mistaken author of the article goes on to summarize that only at dinner did my companion figure out that my intentions were to have a date. Referring to my email above, it's pretty clear that facts were drastically changed -- in fact, reversed -- here: I was the one who'd been allowed to operate under false pretenses, not he, and the result bothered me quite deeply.

I admit that it's fairly ludicrous, but at this point, seeing how poorly and ignorantly my initial date request (and yes, my feelings) have been handled, I am asking myself whether this behavior technically constitutes homophobia -- albeit insidious and perhaps unintended. Without a doubt, my former dinner date would be horrified if someone thought that of him; he surely considers himself 500-percent pro-gay. Hell, he may have even made "playing gay" into a specialty of his in the workplace in order to fit in or make things less complicated. It happens a lot these days. In any case, I'm certain that he makes sure to address gay people in general with respect, consideration, decency and the like. But especially after reading the post from last week, I only wish I could have been treated in the same way.