I didn’t catch it at first, but I now realize that something important was left unexplained from our last conversation. You, a man of high self-awareness, contended that your risk-aversion holds you back in matters of love. This didn’t strike me as true since an obvious manifestation of risk-aversion is settling for a “good enough” girl who checks many boxes and provides undeniable aid against loneliness – and you don’t do this. You, in fact, are likely to hear pleas from friends to be “less picky” and other such well-intentioned nonsense that risk-averse individuals utter to risk-lovers. I guess xxxxxxxxx simply had a blind spot in his self-model and risk-aversion isn’t plaguing him.

But that’s too easy a conclusion, right? You have thought about yourself and love a lot, and surely you considered that which I noticed in 60 seconds:

As I tell my undergraduate students, whenever they encounter in their required reading a claim or argument that seems just plain stupid, they should probably double-check to make sure they are not misreading the ‘preposterous’ passage in question. It is possible that they have uncovered a howling error that has somehow gone unnoticed by the profession for generations, but not very likely.

–Professor Daniel Dennett

So, I went back to a base assumption that you were indeed correct about yourself – risk-aversion was hurting your chances at love – and generated some ponderings that may (or may not) be applicable.

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There exist a range of risks potential lovers take en route to mystical oneness with another. Go talk with the girl at the bar? Risk. Send a text message declaring your excitement about an upcoming date? Risk. Try to hold her hand? Risk. Proclaim “I love you”? Risk. And on and on. Some risks are small. Some are big. All share the commonality that however confident you may be, you may, in fact, be out of alignment with her, and thus rejection is a possible outcome. It is this dreaded result more than anything else that causes people to act not out of desire or honesty, but out of a wait-until-it’s-oppressively-obvious-such-that-rejection-is-damn-near-impossible defensive crouch. This cautious approach can also be applied inward in the form of waiting, waiting, waiting until you are totally certain of your own feelings. A form of safety is certainly guaranteed through inaction. However, the cost for such safety is that one misses out on the possibilities (probabilities?) that divulging an inner mess of emotions (a) builds intimacy and (b) actually helps one resolve the emotions.

For almost all of my life I was incredibly risk-averse with girls. I wanted it to be easy for me; I’d hope and dream that she would make the first move (in all senses). Even when I’d receive what an impartial observer would consider clear validation, I remained scared. I remember one particularly painful encounter with this beautiful girl named xxxxxxxxx at a wedding. While I’m freely acknowledging my past risk-aversion, it still amazes me that I didn’t kiss her. I knew my error as I drove to the airport the following day screaming at myself Whatthefuckwhatthefuckwhatthefuck. That’s when I began constructing the foundation to one of my core philosophies:

A significant part of “knowing thyself” is knowing what you will regret.

For teens devoid of experience, predicting future feelings is rather challenging – highs are higher and lows are lower as a result.

With, however, wisdom and the accompanying confidence to say “I know who I am,” if you pause before making a decision, an accurate sense of what action will produce regret appears.

And just like that you have earned a remarkably robust, intelligent philosophy for a good life: anticipate regret and avoid it.

Unfortunately, I didn’t instantly transform into a person who optimally practiced the philosophy. It took time, and multiple other failures (xxxxxxxxx!!! Why-oh-why was I such a coward?), to fully appreciate what induced the sharpest form of regret in me and begin avoiding those behaviors.

Rejection always sucks. For the sake of self-preservation, all sorts of defense mechanisms are employed to lessen the pain. Like, She didn’t really know me, which means YOU weren’t really rejected, just a superficial version. Defensiveness works, but in an entirely pernicious way since it encourages ever less sharing of your “truest self” so If only I had done [insert action your truest self would take] remains plausible.

Perhaps it’s not obvious why this type of self-preservation is terribly pernicious. After all, I didn’t fully comprehend the costly tradeoff for most of my life. To be happy, tranquil, “at peace,” etc. you must be pleased to be you. If you like life as lived by you, your candor and vulnerability are required for flourishing. So, you must take the risks your weakness would have you avoid. Being strong, not weak, propels one into a wonderful place devoid of assuaging stories to deploy if things don’t work out.

I only ever reached this place in my last relationship. With a fearless confidence, I said everything I wanted to say, including all my shortcomings, vulnerabilities, fears, uncertainties, but also all the glorious truths. I also did everything I wanted to do, generally in a type of honest flow. She knew it too and would warn, as the relationship hurtled back toward a crash landing on planet Earth, that I was “too exposed.” I laughed then. I laugh now. She was possibly correct that rejection while totally exposed hurts more than the alternative. But that alternative where you can claim I didn’t even really want the girl means you never give everything to anything; you live beneath your capabilities and have to grapple with the deep regret of What if? The pain of pondering that over and over and over and over is worse to me than the pain of being purely rejected for who I am. Furthermore, I’m living to chase peaks, and the price one must pay to reach the highest of highs is full exposure. When the upside is so grand, there’s no other viable choice.