The Trap of the Self-Assured Don Juan

Why The Kind and Confident Don Juan You’re Looking For Doesn’t Exist

“Fake it til you make it” is a cliche that’s repeated ad-nauseum, one that most of us latch onto as a way to impress our bosses, our friends, and, especially, our potential mates. During dates, we try our hardest to connect with those who ooze confidence, often finding ourselves falling for individuals who are so confident that they somehow forget that we even exist. Confidence is sexy; confidence is desirable; confidence indicates strength and power; yet, confidence is bullshit.

In my quest for authentic connection, the major lesson that experience has taught me was that; I’ve learned to stay away from those who appear to be absolutely sure of themselves. In evolutionary terms, it’s understandable why women, and even some men, seek out confident partners; if you’re feeling incapable of taking care of yourself, it makes sense that you’ll want to form an attachment with someone who makes you feel secure, but the person who’ll make you feel safest is the loudmouth who won’t shut up about his exploits. Just as men tend to fall for dependent women, those who don’t challenge or defy them, women fall for narcissists, the dudes who exude self-assurance. Convinced that they’ve found safety, confidence devolves into manipulation, and sometimes even abuse.

Security and high self-esteem (aka conditional self-regard) are two sides of the same coin, which highlights a wild goose chase, frequently ending in tragedy. As we seek out our future mates, it isn’t authenticity we’re searching for but the fulfillment of some personal need; for men, it’s often validation and admiration, and for women, it’s security, and the sense of being protected by a prince who turns out to be a wolf. In a great blog post in Scientific American titled Why Everyone is Insecure (and Why That’s Okay), Ellen Hendriksen argues:

What’s the opposite of insecurity? Total confidence? Complete fearlessness? At first, that sounds amazing. But be careful what you wish for. Only 1 percent of the population has achieved this dubious goal: psychopaths. Turns out a total lack of insecurity is actually a sign of things gone wrong.

But, total insecurity has consistently been the hallmark of the desirable male, which underlies the need for a mass shift in our collective psyche, particularly as it pertains to dating.

I’ve known several men who’ve perpetrated the fraud, pretending to love themselves and their partners, as they lied to, cheated on, and then subsequently abandoned them; their common desirable trait: confidence. These guys talked the talk, but ran for the hills when it was time for their self-esteem to translate into intimacy and security, leaving their significant others behind, isolated and broken. I believe that experience is life’s best teacher, and unfortunately, most people have to learn these lessons the hard way, especially if they’re convinced that their partners are good people who simply need to be loved.

In the same article, Ellen asserted that “A little insecurity in each of us maintains social cohesion rather than letting rampant psychopaths drag down the whole group,” So, rather than allowing oneself to be duped, it may, instead, be wise to search for sincerity, dumping the impractical wish for security. We were tossed into a random world, full of random people and random events; it’s chaotic and scary, but we don’t have to make our lives even harder. Returning back to the theme of evolution, there’s a reason why all of us are insecure, because insecurity serves a valuable purpose; as Ellen noted:

Insecurity persists because it buys us more than it costs us: self-awareness, safety, group harmony, belonging and a much better life than that of a psychopath.

So, for those of you on the seemingly unending quest for the perfectly confident man, remind yourself of perfection’s phantasm, which serves as a mask for a vulnerability that isn’t discontinued just because it’s hidden. In essence, security isn’t real, at least not in the black and white sense in which we perceive it; no one can shield us from the world, not for the rest of our lives. And, we can’t forget that it’s up to us to create them. The real strength lies in the display of vulnerably and one’s willingness to be rejected for their true self. Although it can’t, and doesn’t, sustain the mirage of security, vulnerability earns its stripes through its ability to foster bonafide human connections; and, they are what all of us are genuinely searching for.

Why Everyone is Insecure (and Why That’s Okay)


  1. I can relate to this a lot. As someone who performs in public (comedian) I’m asked almost weekly “do you get nervous before going on?” Absolutely is always the answer. If I wasn’t nervous I font think what came out would be that likeable. When I teach comedy in workshops I always tell peoe the number one tool they have to connect with an audience is self deprecation. My job is to expose my weakness’s and be able to laugh about it. Its about landing face down in the mud…but then standing up, dusting yourself down and going, ‘Hey I seem to be OK’ The more we accept our vulnerability the better we are with others. Great article. Much thanks for writing. X

    Liked by 1 person

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