“Tails.” I spoke the word out loud with my indoors voice. I ordered white tails to wear at my high school prom.

For many American high school students, senior year means at least two things: Graduation and Senior Prom Night (and the morning after). With no research, I can tell you that “prom” is short for “promenade,” which is long for “prom.” For naive bookworm me, the prom, far more than graduation or even theconstantthinkingofthoughtsabouttherestofmylife, was the source of many anxieties.

(There is an ancient cliché about how native peoples who live in the Arctic have 1000 words for snow because they know snow so intimately that they have 1000 words to describe 1000 unique realities. Replace the word “snow” with “anxiety,” and you have me. A thousand different anxieties.)

I had not yet asked a member of the female population for a date, or a kiss, or anything. Of course, several of my closest high school friends were female, so I had many examples of real-life interactions between me and female women that I could draw from. I did not draw conclusions from these real-life examples of human beings in my midst, however. It did not occur to me until just now, at age 46-and-a-half, that there were probably fellow boys in my high school class who looked at me and envied what they saw: a boy who talked easily with girls.

This is not to say that the idea of requesting a date from one of my female friends did not occur to me; it occurred to me continuously. I did not want it to be obvious, so I did not ever speak the words, “Would you like to go out with me?” in the presence of any other human being.

The soap opera that is the life of almost every 17-year-old child-adult resulted in me having a date to the prom, thankfully. But I was a bystander, an onlooker to the entire thing. J—– was one of my best friends in high school and she had her sights on a someone who had asked a third, different someone to the prom instead. The someone whom she had her sights on was a boy whom I remembered from elementary school but who had dropped off my radar so completely that I did not know he was a student in our high school much less graduating with us. (And we were students in a small district; my graduating class was only 120 students or so. I thought I knew every single classmate, as I edited the student newspaper. Like many a newspaper editor, the population kept me in the dark about a few things, like everything fun.) He rode a motorcycle and he illustrated comic books and he did not attend class and my personal jealousy when she told me about this was total.

“You-you like him?” (I liked her, but I had never wanted to be so obvious as to express it.)

“That’s not why I’m here,” she replied.

J asked me to our senior prom. She was wise enough to know that she needed to handle my young ego as gently as any world diplomat tasked with organizing place settings at a conference, yet as firmly as a school principal. We were going to attend together, but stag, as two friends. It would be as if I was attending with one of our male friends.

Of course, all I heard after she asked me out was nothing. I was going to the prom. The rest was lost in the fact that I was going to the prom, and with a woman.

(She and the motorcycle comic book artist met up at the prom and left together. I was home and in bed at a reasonable hour, if by bed you mean the back of my parents’ station wagon, and by “at a reasonable hour” you mean the following night. I was still a year away from consuming my first drink, but I was ready to embrace the “lifestyle.”)

For many American high school students, the prom means renting, buying, or inheriting from a recently deceased family member some elegant formal wear. (The less expensive the formal wear, the greater the chances the word will be spelled “elegante” and be italicized.) As with all things to do with fashion, men have a uniform with little variation (some sort of a suit) and women have more choices.

I like wearing suits for two reasons: 1. I am an anxious person and a suit feels like it is something that is tightly holding me together and preventing me from exploding, and 2. compliments. But I should not be in charge of ordering the thing. I am a thin individual and for decades I attempted to mask this with over-sized clothes. The result was that I usually looked like a person who had been partially consumed by his suit, which was patiently waiting for the right moment to swallow that last morsel, my head. (I am too fond of that joke.)

Formal wear means a tuxedo. And there were two types of tuxedo I had yet seen: Fred Astaire in a top hat and tails, and everyone else. The “everyone else” sort of tuxedo looked to my eyes like a simple business suit. Thus, I explained to my father that I did not think that “anyone there” was going to look like “everyone else.” I wanted to look like everyone else not looking like “everyone else.”

No one ever tells me that my theories are idiotic. I somehow always convey an authority that I do not possess and do not feel like I possess.

White tails. I ordered white damn tails. My non-date, who was wearing a tasteful and elegant—definitely not elegante—cocktail dress when I retrieved her, did not snicker at the sight in front of her. But I looked like I had been hired to drive her there and then wait with my horse and carriage to drive her back home when her magical evening was done. I looked like I was going to pull a dove from my sleeve at any moment. Any photo of us from that night looks like two photos that have been inexpertly spliced together. Well, we had two very different nights anyway, so this is appropriate in an existential way.

What I remember from that long-ago May 1986 weekend is just a few things: the idiotic tuxedo I trapped myself into (the only pair of tails at the dance), the fun and funny conversation my date and I had the day after—when we went back to being the friends part of “just friends,” and hearing this song over and over and wishing someone was stuck with me:

 
 
It only took almost three decades, but …

 
(I love you, Jen.)

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This is lightly edited from a May column.

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