Devil’s Advocate for the Shy

Joe, I am an attorney in the employ of Lucifer, the Prince of Lies, and I’m here to help you. It is true that the shy and the socially inept, like you, are doomed to a life of emotional desolation, but knowledge and techniques exist which, conscientiously applied, work just well enough to maximize your frustration.

Before we get started, I’d like to admit that corporate anti-harrassment policies are one of my finest achievements. The delicate balance between harming the innocent and failing to protect true victims is a wonder and a delight. The Boss is pleased, too.

social skill as a sense modality

In a normal human being, basic social insight is a perceptual process. The normal can recognize social situations and the emotional responses of others as gestalts in a direct and effortless way, without conscious thought, much the way that they recognize forests and beanbag chairs. Persons with diminished social skills exhibit correspondingly diminished ability to perceive their social environment. Those with no social skill whatever are blatantly pathological, and the Boss has intervened personally, to ensure that evil is optimally wrought, by keeping these individuals as long as possible out of institutions.

I am sorry to say that you do not fall into the final category above. It would simplify your life.

coping with partial social blindness

According to carefully-planted and plausible rumor, the partially blind step cautiously and feel their way around obstacles that they can’t quite make out. The totally blind walk forward with confidence and display permanent shin bruises.

To ensure your final deception, I am compelled to admit that the rumor is not always true. As a person suffering partial social blindness, you face continual choices between the whirlpool of not getting anywhere and the rock of bruising your heart.

Let’s be concrete about that rock. In a case like yours, of asking a woman out, a guy of good social skills will notice her feelings as easily as noticing the weather. If he needs to crack open a window to check the temperature, he may do so by lightly lifting the conversation into the sensitive realm and observing the breeze. Alternatively, if less skillful or more playful, or if the target in the crosshairs is less open, he may resort to innuendo and shoulder touching, thus allowing interesting interaction while maintaining plausible deniability. These are sophisticated procedures, but to the skilled they are no more difficult than the sophisticated procedure of drinking from a glass of water.

To the unskilled, these procedures are as valuable as the procedure of programming your computer with a hammer; it works as long as you want to program it to stop. Your method, of bulling through the china shop and asking her out without preparation or foreknowledge, is a poor substitute. In this specific instance, it had the benefit of getting you into trouble, but in the typical case it merely shortens your period of confusion and hurt—and on rare occasions she may say yes, thwarting the infernal will, an outcome it is best not to risk.

Therefore, speaking officially for the devil, I advise that you follow the more considered path of becoming friends first. Do not mention your feelings at first. Chat over lunch, and do the movie and museum things, and offer your opinion when she’s debating laser eye surgery. Then, then go for it. This is more likely to be successful, because one whom you have come to understand and care about, and who you know cares about you, can cause deeper and more lasting pain with her rejection.

substituting cognitive for perceptual ability

The Lord of Hell and I are in agreement that those who cannot perceive the lay of the land should strive always to infer it from indirect signs. For example, imagine you are proposing a first dinner date to your new friend, and she says yes with definite hesitation.

Joe: So, you wanna go to, uhhhh, [thinking fast] McDonald’s tomorrow?
victim: Well....
Joe: You know, to, uhhhh, talk about the weather.
victim: Well, I mean, well, ok.

In this situation a guy of good social skills will, as swiftly as James Bond but more suavely, recognize her word selection, tone of voice, expression, posture, and a dozen other factors that you never visualized as visible, as indicating that she is nervous because she doubts her good luck, or nervous because she doubts your nefarious intentions, or nervous because she fears her medication is wearing off, or whatever it may be.

You, on the other hand, recognize nothing at once but that she said yes. But that night you can play the scene over in your mind and try to draw conclusions—and you should, because although there is a danger that you may come to understand that which was previously dark to you, there is a greater chance that, by turning the incomprehensible over and over, you will wind your emotions to the breaking point and blow your chance the next day in McDonald’s.


In short, the principal principle is to work slowly and carefully so that, when your hopes are dashed, they are dashed all the harder because you tried your best. Satan will thank you for it.

A very different take on shyness is the Shy People’s Dictionary.
Original version, January 2003.
Updated and added here November 2011.