Curiosity: Annals of Online Dating, Part Two

This is my second dispatch from the brave new world of online dating, just over a month after I posted the first one. This essay comes with a premium, like the toy in a box of Cracker Jack: a pocket guide to constructive curiosity, a skill that will improve any man’s chances of dating success. Read on to download it.

On the whole, online dating has been tremendous fun. I like meeting men I would never otherwise have encountered, given that our social and professional circles don’t overlap by even a single degree. Who are these people whose orbits never intersect with my own? What do they think about? What matters to them? It’s like browsing in the sections of a bookstore I don’t usually frequent: I may not end up buying a book, but reading a few lines can be surprisingly interesting.

The dating equivalent of reading a few lines is asking a few questions. When I was young, girls who were interested in boys were trained to create a context for the dating experience, to supply the connective tissue. By the time a girl began to date, she had thoroughly internalized the message that it was her job to be interested in whatever the boy cared about, to draw out his passions and pastimes, to make him the center of attention. Girls were taught to offer an unending stream of questions and prompts, while boys could fulfill their appointed roles by providing the answers.

Such training must have sticking power—for both sexes—because it keeps showing up. Quite a few of my online encounters have turned into in-person meetings for coffee or a walk. I quickly realized that a chief indicator of the prospects for a second meeting was whether my companion exhibited curiosity about me by asking questions. More than half haven’t passed the test. (The rest don’t need this advice, but may enjoy reading it nevertheless, just for the pleasure of feeling affirmed.)

During one long walk, I learned about a man’s career, his entrepreneurial sidelines, his children (and their careers and entrepreneurial sidelines), his roommate, his houseplants, his health, and his views on several controversial issues of the day. As we walked toward the parking lot, I extended my hand to take my leave. He said something about his parents’ marriage that made me volunteer a snippet of information about my own past. The river of I, me, my stopped flowing for the first time in an hour and a half. He stared at me with wide-open eyes, realizing that he had no more idea of who I might be than before we’d met.

The male friends I’ve consulted about this issue have consistently said the same things: that many men don’t know how to express their curiosity, they aren’t trained to ask questions without feeling like interrogators, or they just aren’t aware of the interrogative part of conversational art. If that’s true, the least I can do is provide a little technical assistance. So as a gift to you, dear readers, and to all online daters, I’ve created a handy pocket guide to getting to know your date. If there’s a spark to be raised, click here for Arlene’s Dating Guide to Constructive Curiosity. These suggestions, judiciously deployed, will help to kindle it by creating a cycle of conversation, a two-way flow in which both parties seek and find.

Two things to bear in mind:

• First, the point is not to amass information about your companion, uttering a stream of questions that can be answered with a number, a date, or a name. The goal is to learn who someone is by exploring how that person thinks and feels.
• Second, no matter how good your questions may be, they won’t help if you don’t listen with full attention to the answers. Not every woman is going to enjoy answering each and every question I’ve suggested. If you pay attention to visual cues as well as verbal responses, you will be able to sense whether a particular question is welcome. Active listening—the kind of focused attention a companion can feel is positive, respectful, and genuinely curious—will help as much as asking good questions.

In the old distribution of dating responsibility, the imbalance in roles often created distortion on both sides. The boy sometimes became inured to a universe centered on his story, with a corresponding atrophy of interest in and engagement with others. Sometimes the girl’s questioning role morphed by degrees into a fairly extreme state of self-abnegation, into trying to figure out who the boy wanted, and then trying to be that girl. I have a vivid memory of eavesdropping on two cheerleaders in the changing room after high-school gym class. “I would give anything to go out with him,” said the tall girl, thinking of a handsome sports hero who happened to be short in stature. “I’d have my legs shortened.”

The new reality can avoid both distortions with a single directive: be real. The thing I like best about online dating so far is the ease it brings to my own experience. At this point in my life, I am who I am, and see no reason to pretend otherwise. In contrast to the bad old days, it is a delicious relief to show up as myself. Come as you are: what a concept! How much fun is that? So far, quite a bit.

I’m surprised at how useful I’ve found it to think of online dating’s challenges in terms borrowed from Nassim Taleb, the self-described “epistemologist of randomness” who wrote The Black Swan, a book I thoroughly enjoyed.

In Taleb’s framework, “black swans” are rare, unpredictable events with large consequences. Some contexts are more susceptible to black swans; Taleb characterizes them as part of “Extremistan.” For instance, mass-market publishing belongs to Extremistan. Of the many thousands of books published each year in English, just a few are likely to account for a large proportion of total sales, while most of the rest are unlikely even to recoup their production costs. Random luck plays a larger role than intention in Extremistan, so when you visit there, the best policy is to maximize your exposure to serendipity.

So that’s what I’m doing with online dating, maximizing serendipity. It is impossible to tell if someone is going to be an appealing companion by reading that person’s vital statistics and personal essays. I like to quote behavioral economist Dan Ariely, who wrote in The Upside of Irrationality that seeking companionship online is like “trying to understand how a cookie will taste by reading its nutrition label.” Some clever and graceful writers freeze up or turn manic in face-to-face conversation. Some men conceal salient facts until they emerge as unpleasant surprises, even lying about trivial personal matters that are certain to be revealed on first meeting—claiming to be a decade younger or half a foot taller— and thus undermining the hope of trust.

Some dating sites are based on filling out extensive questionnaires or responding to a large number of questions posed by other users, matching participants by their responses to yield a percentage or slot them into categories: you and another person are a 92 percent match, or you’re both “explorers” or “negotiators.” So far, these numeric factors and labels are nearly meaningless. I’ve been matched more than once with right-wingers seeking a “God-fearing Christian woman,” clearly not me. Some sites clothe this process in scientific garb, crediting a PhD psychologist or the designers of an elaborate computer algorithm. Taleb has a nice way of seeing this too, best summarized in his book’s glossary:

Empty suit problem (or “expert problem”): some members of professions have no differential abilities from the rest of the population, but, for some reason, and against their empirical record, are believed to be experts: clinical psychologists, academic economists, risk “experts,” statisticians, political analysts, financial “experts,” military analysts, CEOs, et cetera. They dress up their expertise in beautiful language, jargon, mathematics, and often wear expensive suits.

So I will not pretend to be an expert, just a fellow seeker who wishes to help. I offer for your inspiration one of the most romantic songs ever written, “The Nearness of You,” in an exquisite version by Louis Armstrong and Ella Fitzgerald.