I’ve never really been cool, and this fact has always bugged me. I’m not telling you this to sound charming or self-deprecating—it’s just the truth. One Monday in third grade, Maggie and Hilary, two kids with real, you know, status in our class, told everyone that they’d had a sleepover over the weekend. Not just that—they’d watched a Tom Cruise movie and had also learned the meaning of the word fiancé. I knew it had something to do with sex, but I couldn’t say exactly what. Maggie and Hilary knew all about it. I had no idea who Tom Cruise was, and I hadn’t been invited to the sleepover. Why not? Oh, I realized right then and there, it’s because I’m not cool.
My sense was that the condition of being cool or uncool was fixed, possibly even congenital. But that didn’t stop me from spending third grade wanting and even trying to be cool, something that I had yet to learn is the best guarantor against coolness there is. Then I spent middle school striving for coolness to an inadvisable degree. I relaxed a little in high school, such that by graduation I probably came as close as I’d ever get to embodying coolness. (It was mostly out of pure burnout; I just couldn’t bring myself to care how I seemed to people who would forget me after September.) Then, through college and my twenties, coolness fell a few rungs on my hierarchy of needs. It was the Great Recession, and passing my classes and getting a job felt—and indeed were—paramount. I figured I could worry about being cool after I got health insurance.
But this wouldn’t last. It dawned on me by my mid-thirties that my personality would eventually become fixed and I could kiss learning new tricks goodbye. The idea that I might have approached the end of my coolness evolution made me start to notice how lame I’d gotten, or perhaps had always been. My uncoolness began to trail me like an uninvited guest every time I ended up sitting in front of another person, which was often.
There were the outward signs, of course. I brought my lunch to work in Tupperware at least once a week. And as though possessed of their own spirit, my hands always seemed to be giving the double thumbs-up. Phrases like “Holy moly!” and “Now we’re cookin’ with gas” would tumble out of my mouth with alarming regularity. In a particularly cursed moment,
I even heard myself say, “Whoa, Nelly!” But the inward signs were more worrying: I understood in theory that the colleagues who heard me declare that we were cookin’ with gas in a meeting wouldn’t give it a thought unless I went on to talk about it at length, and yet that is exactly what I did. “Was that so weird of me?” I would often message a tolerant coworker after a particularly nerdy or high-strung moment, reminding this person once again of my foible. A version of “I’m begging you to just play it cool” always followed.
I found myself desperate for approval and then, worst of all, showing it. Like a person who frowns for too long, I feared that if I didn’t stop this behavior, it would harden and leave me in a rut. I might spend the rest of my years on planet earth being uncool—and I could not have that. Despite knowing theoretically that the striving was what was making me uncool in the first place, I was willing to give it one last push. For decades, I’d been endeavoring to get cooler while still trying, on some level, to play it cool. I decided to finally say, “Screw it.” I’d take that effort and make it deliberate, then once I succeeded, I would write all about it—teach the uncool masses how I did it. I would become cool.
First cool thing I would do? Work up a meticulous plan for my transformation. It would be research-heavy and rigorous. If I could find a way to peer-review it, I would. The plan would start with phase one: appearance.
In the 1990s, it was illegal to make a movie for teenagers in which the dweeby protagonist doesn’t remove her glasses in the final twenty minutes and become the object of everyone’s desire. This was usually presented as the final step in a journey ninety minutes in the making, but it struck me as, actually, the easiest part. So I decided to work my way in from the outside. After all, this is Esquire, and cool clothes are just lying around here. I noticed that my most fashion-forward colleagues always seemed to be wearing cheeky little accessories, so I got one, too: a black baseball cap with an image of Smokey Bear embroidered over the words ONLY YOU. I started wearing wide-legged pants and socks that went halfway up my calves. I futzed with my part to try to center it on my head like my Gen Z coworkers did. I experimented with loud nail polish. I didn’t ditch my glasses, but I did upgrade them to something geometric. (They looked terrible.) It probably goes without saying that I got a leather jacket.
And yet I basically felt the same. Mortifyingly, I often asked those around me if my transformation was succeeding. “How cool is this hat?” I asked a friend’s girlfriend, pointing to Smokey. The girlfriend, a multi-hyphenate artist of some kind, smiled brightly and told me it was “great!” in a tone I recognized from the feedback I give my toddler on her drawings. The changes I’d made to my presentation had perhaps run their course.
Now that I looked the part, it was time for phase two: I had to study up. Whatever was happening inside of me was certainly the opposite of cool, but I found it difficult to define what “cool” actually does mean. Fortunately, there’s something of a micro-genre on this subject, so there was plenty to read. When a (fantastic!) book called American Cool: Constructing a Twentieth-Century Emotional Style, by the historian Peter N. Stearns, arrived in the mail, my husband glanced at its title and went wide-eyed. He said, with a voice full of gentleness, as though confronted anew by the awesomeness of my loserdom, “Oh, boy, you’re up against it.” Unstudied nonchalance is key, he explained pityingly, and the purchase and subsequent reading of a book, especially on this topic, is the opposite of unstudied.
I chose to ignore him (which I decided was cool of me) and read the book anyway. In it, Stearns takes a tour through Victorians’ “emotional culture,” in which to keep “cool” was to avoid not just showing but even having intense emotions. The sense at the time was that emotion was actually dangerous. Writes Stearns, “The positive connotation of ‘cool,’ along with its increasing usage, symbolizes our culture’s increased striving for restraint.” He argues that it’s uniquely American to fixate on coolness and that it weasels its way into everything we do as a people, from raising kids to watching movies to buying cars.
A classic in the What Is Cool genre is Anatole Broyard’s 1948 essay in which he tries to define the hipster, titled, logically, “Portrait of the Hipster.” He followed this study with another one called “Keep Cool, Man” in 1951. Both pieces define hipster and cool in relation to music and race. The first gives hipster a specific definition: a Black person who listens to a lot of jive music, although “the hipster rarely danced; he was beyond the reach of stimuli.” (“Beyond the reach of stimuli” sounded incredibly nice.) The second describes a different sort of person. “Now in Harlem,” Broyard writes, “the key word is ‘Be cool, man.’” Coolness, in his telling, was a response to the racism and brutality the world inflicted upon Black men. (He doesn’t necessarily approve of it—he seems to consider that being cool, man, amounted to “draft dodging” in a war against oppression.) The writer Mark Greif puts his finger on a much later iteration of the hipster with his 2010 essay “What Was the Hipster?” He locates the hipster geographically (Wicker Park, Williamsburg), lists the hipster calling cards (big glasses, PBR, bands you’ve never heard of), and identifies his inherent contradictions (uneasy relationship with capitalism).
All this was interesting, but I had to admit that the history of the word and the attitude is not an instruction manual, which was what I so badly needed. With not a little bit of embarrassment, I searched “how to be cool” in the online library of user-generated advice, WikiHow. There I found a practical guide at the ready for me, complete with illustrations:
“Have you always wanted to be the cool person, who always seems to do the right thing and flows through life with ease and grace?” it asked. That was me.
“Or are you learning to be the chill person, who never seems stressed or nervous and has an air of confidence?” Of course.
“There’s no reason you can’t be like that yourself.”
This was stupendous to hear. Especially after all this reading about jazz. Did it categorically preclude me from coolness that I was reading this web page at all? Definitely, but who cares? (I was off to a good start.)
Step number one was “Don’t be needy.” No more messages to my coworkers looking for reassurance. No more requests for pep talks from friends. No more seeking external validation. WikiHow told me to be myself and to have a sense of humor but also to be a good listener, to be a good conversationalist, to be “friendly, but not excessively eager.” Yes, I nodded along, remembering what Stearns said about how coolness is all about restraint. As though it had heard me say, “Whoa, Nelly!” WikiHow counseled me to “refrain from using too many colloquialisms. This may make you appear as ‘fake’ or unable to grasp your respected language.” Although this piece of advice struck me as rich coming from a website that read like a brochure welcoming humans back to society after a period of cryogenic freezing, I took the point.
The site’s final tip:
“Don’t just think about it—do it. It’s all very well to read books and blogs about self-
improvement, but you have to actually get out there and apply the theories that resonate with you. Do it! It’s scary but so, so invigorating. Who knows who you’ll meet and what they might be able to offer you? (Fun, intellectual stimulation, a pony ride, a job, etc.)”
I wasn’t sure where to find a pony on short notice, so I disregarded that part. But point taken. Enough reading; time to get out there. I went out with two friends and our preschool-aged kids and described my plan to the group, asking them for advice about how I should go about it. “You’re already cool,” one said, as the other nodded along and punched a straw into a juice box. I cherished this feedback and momentarily considered calling my editor to declare the project off—I was already cool! Then I looked around me. I was at an event showcasing historic buses of New York City. I had to get serious.
I brainstormed a list of cool people I know personally and began to systematically survey them for their advice. This felt like a logical choice, given that in addition to the historic-bus friends, they’re the people whose opinions I care about most. Then I spent afternoons trying to come up with a place that would seem cool to these friends, and then I’d invite them there after work, interrogate them, and take copious notes. What does it mean to be cool? How did you get this way? I’d ask. A friend of mine who always seems to understand the mood of the room, another who is kind and understated without being boring in the least, and a third who appears unruffled and easy most of the time would all invariably wince, shift in their seat, and ask, in so many words, “Is this why you wanted to hang out?”
The one who’s so good at reading the room told me to cultivate an air of mystery by talking less. Tamp down my tendency to tell stories about my life. Ask people about their lives. Do not bring up buses. This is all good stuff, I’d think, scribbling furiously. Over beers at a bar in Brooklyn that took only cash (I was careful to find this out in advance and hit the ATM on the way), a friend looked up from her pilsner and, with obvious pain in her eyes, told me, “I think you should stop doing this.”
These cool people who thought I needed to pipe down had one thing in common that I couldn’t overlook, though, a thing that made their advice suspect on its face: They were all my age. Life is long and dynamic, and there are plenty of ways that one’s personality can grow and change for the better from middle age to death, but I sensed that coolness was one area where things stopped developing meaningfully after the age of thirty-five. As my fellow millennials and I found ourselves displaced in the coolness rankings by Gen Z, the mirage that was our youth was fading. Bands that were once a reliable substitute for coolness were now just bands that middle-aged people liked. I listened to a lot of Spoon during that short but sweet time in high school when I had a borderline-cool way about me. I still do. That is decidedly uncool. This is how I talked over all those beers in all those cool establishments. I sounded insane. All of this concerned me greatly.
So I asked a twenty-four-year-old coworker I barely know, one of the ones with all the cheeky accessories, what she thought. As is considered cool among members of her generation, I did this over our interoffice messaging system. I wanted to know what makes a person cool, but I also wanted to know what I specifically could do to improve my station. I expected that she’d name some bands other than Spoon I should go see, but instead she typed back: “I would say that it is paramount to stop telling people that u arent cool. sometimes u have to fake it til u make it and saying u arent cool isnt a cool person activity u get me.”
The answer had come back unanimous. From my middle-aged friends to Anatole Broyard to my Gen Z coworker who’d recently managed to pull off a denim tube top, they all seemed to agree that the issue came down to one thing: confidence.
Okay, so I’d have to get some of that. Mind over matter. I realized that although I could never pull off a center part, much less a denim tube top, and had been pronouncing Chappell Roan “shah-PELL Roan” for months, there was no need to work myself into a lather over it. I could even keep using finger guns and saying stuff like “That’s showbiz!” if I did so without beating myself up for doing so. Maybe it could be cool to be uncool.
This was freeing and even fun. But despite the sunshine it brought my way, there was an undeniable shadow. I could not fully stop caring about what others thought of me. Perhaps most importantly, I could not truly hide this fact. But why? Why does anyone care about being cool at all? Don’t we know that our democracy is on the brink? Don’t we know that North Korea has nukes? Don’t we know that the planet is burning?
It occurred to me that maybe these questions were why I cared. It wasn’t that I wanted to be cool in spite of the fact that we live under constant threat; it was perhaps because of this. I foresaw a future in a bunker of some kind, and would I be allowed in if I wasn’t cool? Back in elementary school, I had felt that life would be easier if I had status—if I was cool. I intuited that there wasn’t enough in the world to go around. At age eight, the commodity in high demand was an invitation to Hilary’s house for a sleepover. But as I approached middle age, the commodities in question had become more important: To be seen as cool was to be seen as relevant, worthy of being hired for a job, of being chosen as a partner or friend. In short, worthy of keeping around. To try to be cool was to scramble for room in the bunker in a frenzy while pretending not to. I was in a lather, and the longer I stayed this way, the less cool I became.
So I did something completely out of character: I gave up.
I hadn’t given myself any kind of deadline to become cool, and at first, this gave the project a vague urgency that made me sweat all summer. But as the weather literally got cooler, the vagueness of the assignment started to look more like a gift. My failures even began to feel like a kind of mercy. By the standards of many—even most—people, I would never be cool.
I did not experience a stand-alone moment during which I decided this was fine. It came over me slowly, and as it did, something awesome happened: I actually got a little bit cooler. Coolness involves a recognition that there are going to be many times in life when you will not only feel uncool, you will actually be objectively uncool. And so what? I would surely keep asking friends for reassurance, and it would embarrass me and them each time. Sometimes I’d do so at work, sometimes at Bus Fest, and sometimes over beers I paid for in cash. We would all live to tell the tale. I’d never be cool, and I’d just have to be cool with that.