So, you know what I thought would be fun as we head into the weekend? (Well, fun for you, anyway; excruciatingly painful for me.) How ’bout if I start a new category dubbed “Embarrassing” (not to be confused with Buffoonery), in which I shall regale you with tales of some of the most embarrassing moments of my entire life? How’s that sound? Good? OK, super!

Why would I do such a thing? Well, most obviously, it gives me something—plenty of things, actually—to write about without having to hope for some kind of daily fiasco to pop up and give me fodder for my next entry; and, secondly, I think it is possible that I may actually find catharsis in airing out these embarrassing moments for all of the Internet. Why should I cringe alone when I can have you all cringing with me?

Now, the only hard part is figuring out just which embarrassing moment I should write about first. Hmmm … well, there’s my entire adolescence … and most of the sexual experiences I had during my late teens and early 20s (meaning, you know, like, those three times) … oh, wait, here’s a good one:

Throughout college, I worked as a bartender at a couple of restaurants on the North Shore. Early on in my bartending years, I learned firsthand that gay men—several of whom I worked with, and some of whom became good friends of mine—are actually just regular human beings whose sexual orientation, it turns out, has absolutely no bearing whatsoever on my life, or the life of the traditional American family. Go figure.

During my subsequent post-homophobic life, I was very comfortable joking with some of my gay co-workers about any number of things, to include their incidental gayness.

The year is 1996 and I am a senior in college. While having one such light-hearted conversation, Michael, one of my gay co-workers, informs me that I am not his type. He is not the first gay acquaintance to tell me this. (For those of you who have not had a gay acquaintance tell you that you’re not their type, it makes for a strange internal dialogue … something like, “Well, it’s probably for the best that he’s not attracted to me, since I am not gay, but, still … what’s wrong with me, huh? I’m a good-enough looking guy, aren’t I? And funny? Hell, I’m a laugh riot. What’s not to like? Why doesn’t he want me??”).

Fast forward to later that evening. An off-duty, female co-worker is standing across the bar from me, and we are having a conversation about who knows what. Somehow, during the course of this conversation, it comes up that Michael had told me I wasn’t his type. It is at this point in the conversation that I turn to Ricky [not his real name], another co-worker whom I had known for quite some time, and say to him, “Ricky, you’re a member of the gay community; I don’t get it. Why do gay men not find me attractive?”

Ricky reacts by looking slightly offended, and says to me …

[Jesus Christ, I want to crawl under my desk right now.]

Ricky says to me … [*gulp*]: “I didn’t know I was a member of the gay community.”

Umm … AWK-WARD.

I have known Ricky for a few years at this point, and, up until this very moment, I was sure that he was an openly gay man—and, in my defense (if it can even be considered one), a very effeminate and mildly flamboyant one, at that. However, in the split second that it takes for all of the blood in my face to drain into my feet, I am able to flip through my entire mental notebook, and nowhere in it can I find a single instance during which Ricky has specifically said he is gay.

I experience mental vapor lock. My mind cannot locate even a hint of a handhold onto which I might grab and save myself from plummeting into an abyss of embarrassment so ink-black and horrifically deep that I am afraid I may never get out.

I say nothing. I turn and look at my female co-worker. Her expression is a combination of profound discomfort at the position in which I’ve placed her, and stunned amazement at the enormity of the gaffe I have just made.

I am certain that I am about to wake up in my bed with my heart pounding, and I will then be able to say to myself, “Holy shit! Thank god that was just a dream! Can you even imagine doing something that embarrassing? Whew.”

Except—fuck—I am awake. Oh no.

Ricky—whose shift is over and who had been just about to leave the building (if only he had left 10 seconds earlier!)—bids us goodnight and departs. I excuse myself from my female co-worker, walk into the kitchen, out the side door, and run into the parking lot, where I catch Ricky just before he backs his car out and leaves. He rolls down his window.

“Ricky, I’m really sorry. I didn’t mean to—”

“It’s OK,” he says.

“Seriously, I’m really sorry, I just thought—”

“Don’t worry about it,” he says and heads home. Never again do we speak about this incident.

Now, let us return to the present, and allow me to ask you: do I have game, or what? I mean, that, boys and girls, is embarrassing. Frankly, I don’t know if I can top that one, so I hope I haven’t set your expectations too high for future installments.

Incidentally, I’m not sure the whole catharsis thing is gonna work out; I have so viscerally relived that incident by writing about it here that I feel like it just happened. Hopefully, there’ll be some kind of purging effect in a short while … one that doesn’t involve me vomiting from the intensity of the embarrassment brought on by that memory.

  |    Subscribe   |     Follow me on Twitter
Filed under Embarrassing  |  Permalink