“Hey, how you doing?” a couple of bandannas, beneath hats turned backwards, and sunglasses asked after pulling their truck over in a neighborhood to talk to me. 

I’d love to tell you that when I braced for the worst, it had nothing to do with their appearance, but that would be a lie. When a couple of young fellas, who were my age at the time, if not slightly older, approached my van with their hats turned backwards, over bandanas, I imagined the encounter a modern-day equivalent of bandits pulling over a stagecoach. I tried to put that over-informed stereotype behind me, and I tried to maintain the belief that they were just customers.

“I’m great,” I said as genuinely as I could. “How can I help you?” I was the ice cream man, the ding ding man, the good humor man, or whatever you call the ice cream van driver in your locale, and they were presumably customers. 

“Do you have a screwball?” one of them asked. I said we did and pointed to the display on the side of the truck for their verification and pricing needs. “I used to love the screwball, with not one but two gum balls at the bottom,” he added

“Not one of my best sellers,” I said to stoke conversation, “but I agree with you. I used to love them too.”

“The Choco Taco,” the other said, as if that’s all he needed to say, and they both swooned with sarcastically romantic smiles.

This brief conversation evolved into other, casual conversations about the business end of selling ice cream products in a van, my compensation, and other such nonsense that lowered my guard. The moment after I felt my initial suspicions subside, I reinforced them, thinking that the only reason they stopped me “just to talk” was to allow their stickup man enough time to sneak around the back of my ice cream truck to complete the heist. I divided my attention between them and my mirrors as a result, watching for any movement behind the van. This hyper-vigilance was the product of the cynical, conspiracy theory guys who lived on the opposite side of street of my sheltered existence. They coached me in the belief that most people are not good until we discover otherwise. “It’s quite the opposite,” my cynical friends informed me, “Quite the opposite.”  

“You guys don’t believe in anything,” I said. “You don’t see anything wrong with that?”

“There might be,” those cynics conceded, “but I will tell you this, two seconds after you lower your defense shield, we gotcha!” They got to me, over time, and in numerous discussions of scenarios and real-life, told-you-so instances, they inched my inches until I saw these two hats turned backwards, over bandanas, as sharks circling, studying my strengths and weaknesses, waiting to see if they could get hurt, seeking points of vulnerability, until they spotted a gotcha moment.    

When I saw no movement around my van, I began to wonder if they were feeling me out, to gauge if I was an easy roll for a future heist. All of this may have been unfair, based almost solely on superficial appearance, but I could find no reason why they would want to stop their truck in the middle of a neighborhood street “just to talk” to someone like me.

I never understood the subtle differences and wide divides between the worlds of cool and nerddom, “And you probably never will,” more than one observer has informed me. In the company of these two bandit looking fellas, it was pretty obvious that I was on the outside looking in. They wore it so well too. They were so calm. Everything they did was so calm. They appeared so comfortable with who they were that I thought of the term radiating self-possession that students who paid far more attention in literature class knew and used. Those two also spoke in an ethereal tone that suggested they were probably potheads, and as one attuned to pop culture references, and pop culture characterizations, I knew that meant that they were way cooler than me. If all of this was true, I thought, and they were thieves, and I was the modern day equivalent to the aproned shopkeeper of the ice cream van, their comparative cool points were through the roof.

We view the world from the inside looking out, of course, but according to my metrics, I should’ve been their superior. I wore better clothes, and I figured I had a better education, but these guys had intangibles that I couldn’t even imagine attaining. They had a look about them, a strong sense of cool, and an aura that suggested that they were just fun loving, party-going types. Such characteristics threw my metrics right out the window. They weren’t stupid, however, and that fact was evident minutes into our conversation.

They asked me questions about how I was compensated. That, in and of itself, is not an informed question of course, but it was the way they asked those questions. It was a feel that cannot be explained that suggested their leading questions were such that they knew more about the business side of life than the average bandanna, beneath hats turned backwards, and sunglasses dude. I gauged their questions appropriately, but I maintained that there was no way their education was as expensive as mine. Plus, I thought, If they were potheads, they probably spent a lot of time equivocating moral issues, and those who equivocate –my Catholic school educators informed me– have fundamental flaws about them that they spend an inordinate amount of time trying to overcome and hide. In my world of proper metrics, I thought I was, check, check, check, superior.

Except for one tiny, little nugget, I conveniently neglected to input into the equation: on this particular day I was also wearing sunglasses and a bandanna beneath my backwards facing hat. The only difference between the three of us was that I didn’t wear this ensemble on a day-to-day basis. I wore it for the sole purpose of concealing my true identity. I was so embarrassed to be a ding ding man that short of wearing a fake beard and a Groucho Marx nose and eyeglasses, I had every inch of my identity concealed from the public.

They didn’t know any of that of course. They probably thought I was a bandanna, beneath a backwards facing hat brutha, and that may have been the primary reason they decided to stop and chat with me in the first place. It may have been the reason they were so relaxed about their status, and my status, and the superior versus inferior dynamic influencing our approach to one another. Within the internal struggle I experienced in this interaction, was a ray of sunshine. I felt superior, because this was a get up for me. This was not my every day apparel. That moment was fleeting even while I basked in it, for I realized that if I was superior I wasn’t doing anything with it, and that fact led me to be embarrassed that I was now wearing a bandanna, beneath a backwards facing hat, and sunglasses. I wondered if I input that variable into the equation if it might actually make me inferior to them.

“Who is your primary customer?” the one who spoke most often asked.

“Kids of course,” I said. I then relayed a number of stories about how my trainer taught me to take advantage of the naïveté of children. “I told him that I was not going to conduct business that way, and he said, ‘You have to. That’s how you make money for your business.’ I reiterated that that wouldn’t be how I conducted business.”

They were fascinated by my stories, hanging on every word, and reacting accordingly. Fellas who feel insecure and inferior, generally tend to try to prove their intelligence by speaking so often that we don’t search for their weaknesses. These guys listened, and they listened so well that it was obvious how comfortable they were in their own skin. I watched them react, and I couldn’t believe it. I realized that when we tally points for determining who is superior and inferior, we often fail to account for how comfortable people are with themselves, regardless the relative circumstances. We input data every day and in every way, calculating our strengths and weaknesses, and some of us find ways of achieving happiness within our dynamic. We’ve been led to believe that achieving vast amounts of money, power, and the resultant prestige are an endgame, and the ultimate goal, and anyone who says otherwise is lying. Very few would deny wanting such things, of course, but some don’t need them for that sense of spiritual completion in the manner others do. Some of us just want enough disposable income to do something with the family on weekends, and what we do on weekends can be as fulfilling, if not more so, than that which the most successful business man achieves during the week.

These two were probably a little bit older than me, but they were still young, and as such, the opportunities for them in the future were as wide open for them as for me, but they were still much more comfortable in their current situation than I was. They learned to live with their limitations, until they were so comfortable with who they were that they were radiating self-possession. I realized that in my bandanna, beneath a backwards facing hat, and sunglasses disguise, I lost so many points in this category that it would be impossible for me to recover in time.

The bandanas, with hats on backwards, and sunglasses did not wear shirts, and they were riding in a beat up, old International truck, that rattled in idle. They were construction workers with deep, dark tans that made their teeth appear whiter then they were when they smiled and laughed. My guess, watching these two twentysomethings speak, was that even though they appeared inferior, they had no trouble landing women. My guess was that among those women who knew them well, there was a whole lot of adulation going on. I didn’t know that to be a fact, of course, but guys like me –who were always on the lookout for what we missed in life– were always looking to guys like these for ideas.

They laughed a genuine laugh at some of the things I said. The matters I discussed had something to do with the business side of being a ding ding man, and how I loathed my current station in life, but I can’t remember specifics. I remember their laughter, however, and I remember wondering if they were laughing with me or at me. At this point in my life, I just escaped a high school that contained a large swath of fellas who were laughing at me. This casual conversation reminded me of those fellas I just escaped, and it revealed the shield that I erected whenever I thought one of them neared.

That takeaway didn’t strike me as a profundity in the moment. It crossed my mind, but I didn’t grasp the totality of what happened between us until they told me they had to leave.

“All right, we have to go grab some lunch,” the one who did most of the talking said, finally ceding to the one who had been attempting to draw the proceedings to a close at the tail end of our conversation.

“Oh, of course,” I said. “We’ll see you later then.” I tried to remain casual, but I actually wanted to keep talking to them. In the beginning, most of my participation was clipped to end the casual conversation as quick as possible to thwart their ability to find an angle on me. By the time they suggested they had to leave, I flirted with trying to come up with a conversation topic that might convince them to stay. I obviously dropped all suspicions at that point, and I actually missed them before they drove away.

As I watched them drive away, it dawned on me that the preconceived notions I had about them were based on my experiences in high school, and I thought about all of the hang-ups and insecurities that plagued me. I realized that these two were just a couple of good guys, and they appeared to think I was a pretty good guy too. I didn’t expect them to want to talk to me, but when they did, I expected them to lose interest quickly. When they didn’t, I realized I liked being the guy they thought I was. Other than appearing to be a bandanna, beneath a backwards facing hat brutha, I wasn’t sure what it was they thought they saw when they sidled up next to me to chat, but I liked it, and while I watched them drive away, I realized I wanted to do a retake of the whole encounter. The next time I saw them, I decided, I would enjoy our conversation from beginning to end, without any hang-ups or preconceived notions, but I never saw them again.

The idea that most people speak in superlatives was not lost on me, but most people who knew me well, at the time, said that I might have been one of the most uptight, frustrated, and angst-ridden individuals they’ve ever met, and the costume I wore that day supported that characterization more than I cared to admit. Very few of those who knew me well have ever accused me of being too relaxed.

It wasn’t until these two were long gone that I realized that my inability to put high school behind me prevented me from enjoying simple, casual conversations with some decent guys who just want to chat. I wondered how many other casual conversations I ruined on that basis. Thanks to my cynical friends teaching me the ways of the world, I learned how to play a proverbial king of the mountain game, a game I often lost in high school, and I was so locked into that defensive position that it ruined my life for years.

Is it true that we’re all searching for a point of superiority, or inferiority, in even the most casual conversations? I don’t know, and some would say no, and others would say hell no! “I’m just asking you what you think about the latest wheat and grain prices on the commodity markets.” So, why do we loathe speaking to some people? Why do we try to avoid them as often as we can, and when we can’t, our goal is to end those conversations as quick as possible. Do they make us feel incomplete and inferior? Why do we enjoy casual conversations with others we deem inferior so much more? The tricky, sticky element of this argument is that we think that in some way, shape, or form the elements of superiority and inferiority manipulate just about every conversation we have, and when we’re proven wrong in some instances, we wish we never discovered it. Now that our mind’s eye is open to this idea, we wish we could turn it off, and enjoy the fruits of casual conversations again.

If it is true that every single conversation has these elements in some form, where was I in this casual conversation with two guys who wore a bandanna, beneath a backwards facing hat and sunglasses? That was never established in a substantial manner, but my takeaway from this particular encounter was that for a very brief moment in my life, I didn’t care, and that might be why I enjoyed our conversation so much that I missed them as I watched them drive away.