For the past few years, I have really pondered what coolness is. There’s such cool music, such as Ian Dury and the Doors. Nothing elevates oneself more than Pink Floyd’s money. To think of it more, many things considered ‘cool’ do require said money. But being simply rich is somehow the antithesis of coolness. Simply being rich often implies lack of taste. Can we therefore deduct that instead of having money, it’s having taste that defines coolness? 

See I have somewhat dedicated my precious life to honing the very pinnacle of ‘good taste’. This, of course, is an unapologetically frivolous and, more than anything, a futile goal for ‘beauty lies in the beholder of the eye’. What I consider the ultimate cool is absolutely nothing in someone else’s eyes. Of course, there are things considered cool universally — part of the ever-feared ‘pop culture’. Because, again, mainstream does not equal cool. It is easy to like pop. Liking pop does not require exploration. Pop doesn’t evoke such deep understanding, say, in juxtaposition, alt does. So, is coolness the ability to like something that is not as easily liked? How do we avoid, in the pursuit of coolness, trying to like something that, instead of being challenging to like, is actually just not that good? It’s a rather fine line. 

There is an excellent book, the object of my ever-lasting praise, The Ways of Seeing by John Berger that talks about advertising and how it deploys ideas of exclusivity and jealousy. It shouldn’t come as news to anyone these days that advertisers haven’t advertised products for a century now, oh no. What they advertise is ideas, concepts, lifestyles, feelings. Products are not there to simply serve their purpose. Products are there to bring us closer and closer to the idea advertised. I have a Smeg toaster I paid way too much for. It doesn’t have any fancy settings. It serves its purpose as a standard toaster, but my god does it feel good to be an owner of a Smeg toaster. I belong to the highly imagined club of Smeg toaster owners. That toaster is a milestone right next to my degree certificate. 

It’s this exclusive club culture that I think ultimately defines ‘cool’. I went on a few dates with this guy who was really into really cool music. He knew a lot of other cool people in the town which made him even more cool. They were this accidentally (or intentionally, who knows) exclusive yet vast network of really cool people and I got to experience a glimpse of that while on dates with this guy. I do, however, go on a lot of dates and my friends were not particularly surprised to learn I keep a matrix of all the dates I’ve had. Some of the main brackets I grade are ‘coolness’, ‘humour’ and ‘charm’ — each surprisingly difficult to come by, not to mention encountering them all in the same person. It was only after a few dates, and thanks to my matrix, that I began to realise this guy — although appearing to be cool — was really quite regular one-on-one. This was a drastic revelation for I realised it was the group of people I had enjoyed spending time with, not particularly this one person in it. 

I went on a few dates with this other guy whom I described to my friends as the epitome of cool. While he did mention his friends, it was purely him I thought the embodiment of everything cool, starting from his upbringing in a different cool country, to the way he dressed as if he was about to head out to the country to do some recreational hunting. He was a rather intriguing mixture of old money style, financing high life and vast understanding of current affairs. On our second, and last, date we went to a park, and I remember him lying on a blanket with a cool hat on his eyes, seemingly spent from a party the previous night. He didn’t say much which added to the unattainableness. This was very much repeated in all his communication. It was as Taylor Swift describes ‘Out of the Woods’: perpetual ambiguousness and constant uncertainty. Looking back, it was just bad behaviour. (I want to mention here, that my own behaviour at the time didn’t boast well for myself either.) 

So, is coolness bad behaviour? Or just plain ambiguity? I’d argue so, since this guy, nevertheless how messed up his actions, to this day remains the epitome of cool I’ve yet to find a match of. It also coincides with Berger’s thesis on how exclusivity is attained by disclosing as little as possible of oneself and therefore gaining the envy of others. This guy remains cool in my mind for I did not have the chance to get to know him at all. In fact, I learned virtually nothing about him. The cool didn’t get a chance to wear out. 

These encounters have left me rather frightful, of getting to know people too much, of never meeting someone who’s genuinely cool even after getting to know them very well. This concern has also brought me to a very topical question of why does it matter so much to be cool, anyway? Is it plain vain to care about one’s coolness as well as the coolness of people around oneself? Am I simply a victim of my own taste? While trying to shift my priorities from coolness to kinship, singlehood has certainly both empowered and enabled the search for cool. Though a fun hobby if all consuming it might leave one stranded in one’s own standards. Trying to keep that in mind.

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