Trying Not To Try

The Big Idea: Why The World's Most Attractive Trait Is... Effortlessness

I am somewhat embarrassed to admit that, back in my graduate school days, I used to try to meet women by sitting in a café “working,” with the classical Chinese texts that I was supposed to be translating ostentatiously scattered around my table. A young white guy, sitting in a café, with his motorcycle helmet also not so subtly perched nearby, reading this densely-printed Chinese book — you’d think at least one of the many attractive women passing by would be intrigued. Not a single one was.

The problem was probably that, as immersed as I attempted to seem in my exotic books, I was no doubt throwing off all sorts of micro-signals of insincerity: eyes constantly wandering from my “work,” turning slightly every time someone new came in the door. I began to suspect what was going wrong, so I also tried really hard not to look around at the various attractive women in my environment, to get really get interested in my work, again with only limited success.



The most ironic aspect of all this was that the Chinese material that I was studying in this café had to do with two important concepts in early Chinese thought, wu-wei (pronounced oooo-way) and de (pronounced duh), that explain why my strategy for meeting women was doomed to failure. Wu-wei literally translates as “no trying” or “no doing,” but is better rendered as something like “effortless action.” People in wu-wei are completely unselfconscious and feel as if they are doing nothing, while at the same time they might be creating a brilliant work of art or smoothly negotiating a complex social situation.



If you are in wu-wei you have de, typically translated as “virtue,” “power,” or “charismatic power.” De is an outward signal that one is in wu-wei, and comes in handy in a variety of ways. For rulers and others involved in political life, it has a powerful, seemingly magical effect on those around them. They don’t have to issue threats or offer rewards, because people simply want to obey them. In ordinary life, de causes people to like you, trust you, and be relaxed around you. Even wild animals leave you alone.



Although, to my knowledge, no early Chinese thinker directly addressed the issue of dating, the applications are clear. Anyone who has ever been single for a significant amount of time, for example, is familiar with the “never rains but it pours” phenomenon: you can sometimes go for long periods of being alone, desperately trying to meet someone but having no luck. Then something happens, you meet somebody, have a great time, and suddenly it’s raining women or men (or both, if you’re so inclined). Attractive people smile at you on the street, strike up conversations with you in cafes. It's not that you've changed your look or had a sudden pheromone transplant. It's about de. You are more attractive to others when you’re wu-wei.



The problem is that it’s hard to know what to do with this knowledge. How do you make yourself not want something that you actually do want? This paradox suggests that there are some basic problems with any strategy that aims to teach you how to fake wu-wei in order to get its benefits. Right around the time I was trying, unsuccessfully, to look cool and uninterested in San Francisco cafes (the mid-1990s) a book came out called The Rules: Time-tested Secrets for Capturing the Heart of Mr. Right, with lots of advice aimed at women about how to attract interest by pretending not to be interested. In other words, it was a manual for how to create artificial de. Despite the enormous amount of money it’s made for the authors, as well as the cottage industry that’s sprung up to train people in “the Rules,” it’s not at all clear that it works very well. Similar guidelines that have been created for men — like Neil Strauss, author of The Game: Penetrating the Secret Society of Pickup Artists — are of similarly uncertain usefulness. The strain of actively trying not to try eventually shows, and it is enormously unattractive to others.

You can’t fake de. Human beings are certainly good liars, but we’re also Super Cheater Detectors, and for very good evolutionary reasons. Many goals in life — happiness, creativity, love — cannot be obtained through direct trying. They need to arrive unbidden, as natural, organic outcomes of a life well lived.

This means that, when it comes to dating, it’s best to refrain from trying too hard. If the early Chinese Daoists and Confucians are not authoritative enough for you, you can also ponder the words of the great sage and musician Jonathan Richman. In a classic Modern Lovers track, he addresses obnoxious “bellbottom bummers” — stylish, shallow men who try hard to pick up women, but end up getting rudely blown off. He urges these hipsters remember the example of Pablo Picasso: “He could walk down the street and girls could not resist his stare / Pablo Picasso never got called an asshole.”

As an historical claim, this is debatable (Picasso was not the nicest guy in the world, and probably got called all sorts of colourful things by women.) As a description of the power of de, however, it can’t be beat. True de, true attractiveness, comes out of sincere absorption into something you care about — artistic creation, scholarly absorption, even a genuine connection with your drinking buddies — not calculated clothing choices or pick-up lines. What you choose to embrace doesn’t matter, as long as it’s something that you’re genuinely not doing for strategic reasons. As Laozi, one of the early Daoists, says, “Do nothing, and nothing will be left undone.”

Edward Slingerland is the author of Trying Not To Try: The Art of Effortlessness and the Power of Spontaneity (Cannongate Books). He is also an internationally renowned expert in early Chinese thought and Professor of Asian Studies at the University of British Columbia.