On Being Cool

“Our need for love lies at the heart of our desire for status.” ~ Alain de Botton, “Status Anxiety”

I was on a coffee date with a successful yet gangly woman who was blathering about her sex life when I was both overcome with sadness and struck by a realization: her attempt to connect with me was dwarfed by her deepest unconscious desire, to be the single thing that she could never be: cool. In the recesses of her highly educated mind, she must have believed, “cool kids talk about sex, I want to be cool, so I should talk about sex.” I found her desperate attempts to be cool tantamount to me believing that I could only be happy if I were 7’ tall. She could dress like Robert Plant and party with burners and billionaires, but she would always be a geek.

Trying to be cool betrays one’s uncoolness.

In the age of social media, the pursuit of being cool has become a defining obsession. It is the subconscious force shaping how we dress, where we live, how we travel, and even how we present ourselves in conversations and online profiles. Beneath the burnished veneer, however, this pursuit is a deeply misguided endeavor — one that foments narcissism, alienation, and a profound inability to connect authentically with others.

Markers of desperate attempts to be cool include…

• Conspicuously wearing brand-name clothing and accessories.
• Announcing shopping, real estate, and bitcoin victories.
• Driving luxury cars or living in fashionable neighborhoods.
• Frequenting trendy restaurants or participating in exclusive hobbies like skiing or horseback riding.
• Flaunting elite travel experiences such as staying at destination hotels and flying first-class or private.
• Pursuing supposed physical perfection through excessive exercise or cosmetic surgery.
• Curating an enviable social media presence with a gazillion followers.
• Namedropping — having rich, famous, wildly successful or cool associates.

At first glance, these behaviors might seem innocuous but when they are performed primarily to project coolness, they become less about joy and more about maintaining a competitive edge in what Guy Debord calls “The Society of the Spectacle,” where life itself is all about our performance for others.

Christopher Lasch argues in “The Culture of Narcissism” that modern society encourages us to view relationships as stages for performance rather than opportunities for genuine connection. This narcissistic approach prioritizes admiration over authentic connection, leaving individuals perpetually dissatisfied as they depend on external validation for self-worth.

This dynamic echoes what Herbert Marcuse wrote about in “One-Dimensional Man.” Marcuse suggests that advanced capitalist societies reduce individuals to passive consumers whose identities are shaped by external forces rather than internal values. The pursuit of coolness exemplifies this: instead of being vulnerable and securely attaching to others, we prefer to be revered as cool. In doing so, we become alienated and trapped in a cycle of ephemeral superficial “Likes,” both online and IRL.

Alienation arises because coolness promotes competition rather than connection. When everyone is striving to outdo each other — whether by owning the latest gadget or posting the most enviable vacation photos — it makes relationships transactional. We measure our worth against others and seek validation through comparison. This leads to feelings of inadequacy and insecurity as we inevitably fall short of the ever-shifting elusive goalposts.

Even those who flagrantly reject mainstream markers of coolness often fall into a similar trap. Conspicuous rejection — like when people haughtily proclaim “I don’t own a television” or “I’m not on social media” — is another form of status or virtue signaling, a performance of alternative coolness.

The competitive aspect of coolness further undermines its promise of belonging. As Todd McGowan explains in “Capitalism and Desire,” capitalism thrives on unfulfilled longing. It encourages us to desire what others have while ensuring that satisfaction remains perpetually out of reach. Coolness operates as such a commodity: it is always evolving, always elusive. To stay cool requires constant reinvention — a new wardrobe, a new destination — new status symbols to keep up with and best the Joneses.

This perpetual pursuit creates hierarchies that exclude rather than include. Instead of engendering community, it divides people into winners and losers in the race for social validation. The result is not attachment but alienation — a sense that we are competing against everyone else rather than finding common ground.

True connection requires authenticity, vulnerability, compassion and empathy — qualities that are antithetical to narcissism. To build meaningful relationships, we must shift our focus from being cool to genuine connection with others, which involves the art of attuning to others: listening deeply to others’ needs, values, and experiences rather than approaching every conversation as a contest or place to score points.

The primacy placed on trying to be cool is sad and desperate. While it promises admiration, it delivers mostly alienation — leaving us disconnected from ourselves and others. As Lasch and Marcuse remind us, true fulfillment cannot be found through external validation.

Would you rather be admired or loved?

We must embrace vulnerability over performance, empathy over competition, and authenticity over artifice. By learning to truly attune to others and find common ground, we can get the love that our hearts truly crave rather than the admiration that our egos want.