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  Fast-forward to the mid-1990s—a world without yentas (and, in most Western societies, without arranged marriages) but before the rise of online dating. Ideals of romance and individual freedom prevailed, which also meant that each person who wanted to find a mate was pretty much left to his or her own devices. For example, I remember well the trials of a friend I’ll call Seth, who was smart, funny, and more or less good-looking. He was also a new professor, which meant that he worked long hours in order to prove that he had the right stuff to achieve tenure. He rarely left the office before eight or nine at night and spent most of his weekends there as well (I know, because my office was next to his). Meanwhile, his mother would call him every weekend and needle him. “Son, you work too hard,” she would say. “When are you going to take some time to find a nice girl? Soon I’ll be too old to enjoy my grandchildren!”

  Since Seth was very smart and talented, it was within his power to meet his professional goals. But his romantic goals seemed out of reach. Having always been the scholarly type, he could not suddenly become a barfly. He found the idea of placing or answering a personal ad distasteful. His few colleagues in the university town he had recently moved to were not particularly social, so he didn’t go to many dinner parties. There were plenty of nice female graduate students who, judging by the way they glanced at him, would undoubtedly have been happy to date him, but if he had actually tried to do so, the university would have frowned upon it (in most settings, office romance is similarly discouraged).

  Seth tried to participate in activities for singles. He tried ballroom dancing and hiking; he even checked out one religious organization. But he didn’t really enjoy any of those activities; the other people didn’t seem to enjoy them much either. “The hiking club was particularly strange,” he later told me. “It was obvious that no one there cared to explore the great outdoors. They only wanted to find potential romantic partners who enjoyed hiking, because they assumed that someone who likes hiking will be a good person in many other ways.”

  Poor Seth. Here was a great guy who could have been very happy with the right woman, but there was no efficient way to find her. (Don’t worry. After a few lonely years of searching, he finally did meet his mate.) The point is this: in the absence of an efficient coordinator such as a yenta to help him, Seth was a victim of market failure. In fact, without exaggerating too much, I think that the market for single people is one of the most egregious market failures in Western society.

  SETH’S TRAVAILS OCCURRED before the emergence of online dating sites, which are wonderful and necessary markets in principle. But before we examine this modern version of a yenta, let’s consider how markets function in general. Essentially, markets are coordination mechanisms that allow people to save time while achieving their goals. Given their usefulness, markets have become increasingly centralized and organized. Consider what makes supermarkets super. They save you the hassle of having to walk or drive to the baker, butcher, vegetable stand, pet store, and drugstore; you can efficiently buy all the things you need for the week in one convenient place. More generally, markets are an integral and important part of each of our lives, down to the most personal choices.

  In addition to markets for food, housing, jobs, and miscellaneous items (also known as eBay), there are also financial markets. A bank, for example, is a central place that facilitates finding, lending, and borrowing. Other market players, such as real estate brokers, for example, try in a yenta-like way to understand the needs of sellers and buyers and match them properly. Even the Kelley Blue Book, which suggests market prices for used cars, can be thought of as a market maker because it gives buyers and sellers a starting point for negotiation. In sum, markets are an incredibly important part of the economy.

  Of course, markets continuously remind us that they can also fail, sometimes dramatically—as Enron demonstrated in the energy market, and as many banking institutions showed in the subprime mortgage crisis of 2008. Overall, however, markets that allow coordination among people are fundamentally beneficial. (Obviously, it would be much better if we could design markets in ways that would provide us with their benefits but not their drawbacks.)

  THE MARKET FOR single people is one area of life in which we have gradually moved away from a central market and into a situation in which each individual must take care of him- or herself. To realize how complex dating can be without an organized market, imagine a town in which precisely one thousand singles live, all of whom want to get married (sounds a little like an idea for a reality television show, actually). In this small market—assuming there is no yenta—how do you determine who is the ideal match for whom? How would you pair each couple in a way that would guarantee that they would not only like each other but stay together? It would be ideal for everyone to date everyone else a few times to find their ideal match, but ruling out a mega-speed-dating event, that would take a very long time.

  With this in mind, allow me to reflect on the current circumstances for singles in American society. Young people in the United States relocate more than ever for the sake of school and careers. Friendships and romantic attachments that flourished in high school are abruptly cut off as the fledglings leave home. Much like high school, college offers a milieu for friendship and romances, but those often end as graduates strike out for jobs in new cities. (Today, thanks to the Internet, companies frequently recruit across vast, geographically dispersed distances, which means that many people wind up working far away from their friends and families.)

  Once graduates land their far-flung positions, their free time is limited. Young, relatively inexperienced professionals have to put in long hours to prove themselves, particularly in the competitive job market. Interoffice romances are generally inadvisable, if not prohibited. Most young people change jobs frequently, so they uproot themselves, yet again disrupting their social lives. With every move, their developing direct and indirect relationships are curtailed—which further hurts their chances of finding someone, because friends often introduce one another to prospective mates. Overall, this means that the improvement in the market efficiency for young professionals has come, to a certain extent, at the cost of market inefficiency for young romantic partners.

  Enter Online Dating

  I was troubled by the difficulties of Seth and some other friends until the advent of online dating. I was very excited to hear about sites like Match.com, eHarmony, and JDate.com. “What a wonderful fix to the problem of the singles market,” I thought. Curious about how the process worked, I delved into the world of online dating sites.

  How exactly do these sites work? Let’s take a hypothetical lonely heart named Michelle. She signs up for a service by completing a questionnaire about herself and her preferences. Each service has its own version of these questions, but they all ask for basic demographic information (age, location, income, and so on) as well as some measure of Michelle’s personal values, attitudes, and lifestyle. The questionnaire also asks Michelle for her preferences: What kind of relationship is she looking for? What does she want in a prospective mate? Michelle reveals her age and weight.* She states that she is an easygoing, fun vegetarian and that she’s looking for a committed relationship with a tall, educated, rich vegetarian man. She also writes a short, more personal description of herself. Finally, she uploads pictures of herself for others to see.

  Once Michelle has completed these steps, she is ready to go window-shopping for soul mates. From among the profiles the system suggests for her, Michelle chooses a few men for more detailed investigation. She reads their profiles, checks out their photos, and, if she’s interested, e-mails them through the service. If the interest is mutual, the two of them correspond for a bit. If all goes well, they arrange a real-life meeting. (The commonly used term “online dating” is, of course, misleading. Yes, people sort through profiles online and correspond with each other via e-mail, but all the real dating happens in the real, offline world.)

  Once I learned what the real proces
s of online dating involves, my enthusiasm for this potentially valuable market turned into disappointment. As much as the singles’ market needed mending, it seemed to me that the way online dating markets approached the problem did not promise a good solution to the singles problem. How could all the multiple-choice questions, checklists, and criteria accurately represent their human subjects? After all, we are more than the sum of our parts (with a few exceptions, of course). We are more than height, weight, religion, and income. Others judge us on the basis of general subjective and aesthetic attributes, such as our manner of speaking and our sense of humor. We are also a scent, a sparkle of the eye, a sweep of the hand, the sound of a laugh, and the knit of a brow—ineffable qualities that can’t easily be captured in a database.

  The fundamental problem is that online dating sites treat their users as searchable goods, as though they were digital cameras that can be fully described by a few attributes such as megapixels, lens aperture, and memory size. But in reality, if prospective romantic partners could possibly be considered as “products,” they would be closer to what economists call “experience goods.” Like dining experiences, perfumes, and art, people can’t be anatomized easily and effectively in the way that these dating Web sites imply. Basically, trying to understand what happens in dating without taking into account the nuances of attraction and romance is like trying to understand American football by analyzing the x’s, o’s and arrows in a playbook or trying to understand how a cookie will taste by reading its nutrition label.

  SO WHY DO online dating sites demand that people describe themselves and their ideal partners according to quantifiable attributes? I suspect that they pick this modus operandi because it’s relatively easy to translate words like “Protestant,” “liberal,” “5 feet, 8 inches tall,” “135 lbs.,” “fit,” and “professional” into a searchable database. But could it be that, in their desire to make the system compatible with what computers can do well, online dating sites force our often nebulous conception of an ideal partner to conform to a set of simple parameters—and in the process make the whole system less useful?

  To answer these questions, Jeana Frost (a former PhD student in the MIT Media Lab and currently a social entrepreneur), Zoë Chance (a PhD student at Harvard), Mike Norton, and I set up our first online dating study. We placed a banner ad on an online dating site that said “Click Here to Participate in an MIT Study on Dating.” We soon had lots of participants telling us about their dating experiences. They answered questions about how many hours they spent searching profiles of prospective dates (again, using searchable qualities such as height and income); how much time they spent in e-mail conversations with those who seemed like a good fit; and how many face-to-face (offline) meetings they ended up having.

  We found that people spent an average of 5.2 hours per week searching profiles and 6.7 hours per week e-mailing potential partners, for a total of nearly 12 hours a week in the screening stage alone. What was the payoff for all this activity, you ask? Our survey participants spent a mere 1.8 hours a week actually meeting any prospective partners in the real world, and most of this led to nothing more than a single, semifrustrating meeting for coffee.

  Talk about market failures. A ratio worse than 6:1 speaks for itself. Imagine driving six hours in order to spend one hour at the beach with a friend (or, even worse, with someone you don’t really know and are not sure you will like). Given these odds, it seems hard to explain why anyone in their right mind would intentionally spend time on online dating.

  Of course, you might argue that the online portion of dating is in itself enjoyable—perhaps like window-shopping—so we decided to ask about that, too. We asked online daters to compare their experiences online dating, offline dating, and forgetting about the first two and watching a movie at home instead. Participants rated offline dating as more exciting than online dating. And guess where they ranked the movie? You guessed it—they were so disenchanted with the online dating experience that they said they’d rather curl up on the couch watching, say, You’ve Got Mail.

  So it appeared from our initial look that so-called online dating is not as fun as one might guess. In fact, online dating is a misnomer. If you called the activity something more accurate, such as “online searching and blurb writing,” it might be a better description of the experience.

  OUR SURVEY STILL didn’t tell us whether the attempt to reduce people to searchable attributes was the culprit. To test this issue more directly, we created a follow-up study. This time, we simply asked online daters to describe the attributes and qualities that they considered most important in selecting romantic partners. We then gave this list of characteristics to an independent group of coders (a coder is a research assistant who categorizes open-ended responses according to preset criteria). We asked the coders to categorize each response: Was the attribute easily measurable and searchable by a computer algorithm (for example, height, weight, eye and hair color, education level, and so on)? Or was it experiential and harder to search for (say, a love of Monty Python skits or a passion for golden retrievers)? The results showed that our experienced online daters were about three times as interested in experiential than in searchable attributes, and this tendency was even stronger for people who said they sought long-term, rather than short-term, relationships. Combined, the results of our studies suggested that using searchable attributes for online dating is unnatural, even for people who have lots of practice with this type of activity.

  Sadly, this does not bode well for online dating. Online daters aren’t particularly excited about the activity; they find the search process difficult, time-consuming, unintuitive, and only slightly informative. Finally, they have little, if any, fun “dating” online. In the end, they expend an awful lot of effort working with a tool that has a questionable ability to accomplish its fundamental purpose.

  Online Dating Going Awry: Scott’s Story

  Think about the most organized people you know. You might know a woman who organizes her wardrobe by season, color, size, and dressiness. Or on the other, less fussy end of the spectrum, a young man who divides his laundry into categories such as “day old,” “okay for home,” “okay for gym,” and “rancid.” Across the board, people can be surprisingly inventive when it comes to systematizing their lives for maximal use, ease, and comfort.

  I once met a student at MIT who adopted an extraordinary method for sorting potential dates into categories. Scott’s objective was to find the perfect woman, and he used a very complex, time-consuming system to accomplish his goal. Every day, he went online to search for at least ten women who met his criteria: among other attributes, he wanted someone who had a college degree, demonstrated athleticism, and was fluent in a language other than English. Once he found qualified candidates, he sent them one of three form letters containing a set of questions about what kind of music they liked, where they had gone to school, what their favorite books were, and so on. If they answered the questions to his satisfaction, he would advance them to the second step of a four-stage filtering process.

  In stage two, Scott sent another form letter containing more questions. Again, “correct” responses resulted in advancement to the next level. In stage three, the woman would receive a phone call, during which she would answer more questions. If the conversation went well, he would move her to stage four, a meeting for coffee.

  Scott also developed an elaborate system to keep track of his prospective—and rapidly accumulating—potential mates. Being a very smart, analytical fellow, he logged the results in a spreadsheet that listed each woman’s name, the stage of the relationship, and her cumulative score, which was based on her answers to the different questions and her overall potential as his romantic partner. The more women he logged into his spreadsheet, he thought, the better his prospects for finding the woman of his dreams. Scott was extremely disciplined about this process.

  After a few years of searching, Scott had coffee with Angela. After meeting her, he was s
ure that Angela was ideal in every way. She fulfilled his criteria, and, even more important, she seemed to like him. Scott was elated.

  Having achieved his goal, Scott felt that his elaborate system was no longer necessary, but he did not want it to go to waste. He heard that I ran studies on dating behavior, so he stopped by my office one day and introduced himself. He described his system and said that he knew it could be useful for my research. Then he handed me a disk containing all his data from the entire procedure, including his form letters, questions, and, of course, the data he’d collected on all the candidates he had filtered. I was amazed and a little horrified to find that he had amassed data on more than ten thousand women.

  Sadly, though perhaps not surprisingly, this tale had an unhappy ending. Two weeks later, I learned that Scott’s fastidiously chosen beloved had turned down his marriage proposal. Moreover, in his Herculean effort to keep anyone from slipping through his net, Scott had become so committed to his time-consuming process of evaluating women that he hadn’t had time for a real social life and was left without a shoulder to cry on.

  Scott, as it turned out, was just another casualty of a market gone awry.

  Experiments in Virtual Dating

  The results of our initial experiment were rather depressing. But, ever the optimist, I still hoped that by better understanding the problem, we could come up with improved mechanisms for online interaction. Was there a way to make online dating more enjoyable while improving people’s odds of finding a suitable match?