I have spent a fair amount of time trying to figure out what it is that is most bothersome about contemporary ideas of coolness and the elitism of hipsters. After all, although I have never been a particularly cool person, the emotional reserve and characteristic mode of irony that marks hipsters and cool people are not unfamiliar to me. My own tendency towards caustic and ironic wit and my own immense emotional reserve, after all, are not so far removed from the coolness that affects not to care what the world thinks while simultaneously and hypocritically desiring the world (or at least those people who matter in the world) to care about one’s own feelings and opinions. But being close to something in one’s temperament and approach does not guarantee that one will be in sympathy with them. In fact, people who are close but not close enough to each other in terms of their own perspectives and views can be the worst of enemies and have the worst of relations, as I have found out much to my chagrin.
A great deal of that trouble has to do with the line between awkward and cool. It is cool to walk into a room and not show any interest at all in what others have to say. It is awkward to walk into a room and to care about people but to go about it in a clumsy and ineffectual way. It is cool to have some sort of flippant comment for anything that someone would have to say when it comes to advice or criticism. It is awkward, on the other hand, to struggle to find the right words to say and only to think of the witty comeback several minutes later after the interaction has ended. The person who is being cool and the person who is sadly awkward are not so different in their makeup and in their basic approach to life. The fundamental difference, though, and what creates a great deal enmity between these groups of people, is that the cool person leans into their alienation and hostility to mainstream culture and their lack of ordinary emotional response to become an extreme or even a caricature of remoteness and glacial emotional reserve, while an awkward person is a restrained and cerebral person who feels alienated from others but would rather not. The cool person is playing to their strengths and not not trying to overcome limitations and shortcomings and blind spots, while the awkward person is trying and failing at the very difficult task of working in disadvantageous and immensely challenging situations that most people take for granted doing well because it comes easily to them.
Even as someone who believes that one should maximize one’s strengths, it is still worthwhile to consider the duties and obligations that fall upon all people regardless of personality type and general approach to life. The obligations of social politeness, of expressing condolences for those who are mourning or suffering and of offering praise and congratulation for good news, are not things that come very easily to some of us. While those of us who are more stiff and awkward by nature may never be able to develop eloquence in such areas as to be writers of Hallmark cards for different situations or occasions, there are considerable values in turning a crippling weakness of being so emotionally reserved as to be emotionally unavailable to being a mostly amusing and benign sort of quirkiness that comes as a result of being a cerebral person who is somewhat too much inside of their own head often. Adapting the attitude that what we are not naturally good at does not matter only alienates us from the great mass of humanity for whom the exercise of human compassion is a very important thing. A naturally restrained and prim person will likely never be able to warm up to the point of being seen as an immensely empathetic human being, but it is a worthwhile achievement simply to be recognized as having human longings and emotions that can be inferred even if they are far less obvious than is usually the case.
A great deal of the alienation that we find in mainstream culture comes from the negative affects of adopting an attitude of coolness towards those we should be as warm towards as possible. An awkward person may still be gentle and kind, and so the warmth of their heart can still be inferred from their behavior, and occasionally even from their restraint. But if we enshrine as the central values of our culture the exaggerated reserve and alienation of hipsters, then we have only ourselves to blame when such people find themselves engaged in constant and brutal hostility towards all that is good and noble in this world, trapped in a cynicism that denies anything noble can exist and continually disparaging the human warmth and kindness that comes naturally to some and with great effort from others as a bad thing. In such a world it is no surprise that generations should be alienated from each other, that men and women should be alienated from each other, that politics should be nakedly partisan, that leaders of government and culture and institutions in general should be corrupt and that we should bowl alone and be trapped inside of our own heads and those people who happen to agree with us nearly completely which are the only humans we are able to stand being around. Desiring to be cool is a trap that makes us worse human beings. As uncomfortable as it is to be awkward, it is only be reaching outside of ourselves that we become fully human at all. And such a task is not going to be done easily or quickly.