After the pleasantries are exchanged and the drinks are ordered, after the conversation moves from jobs to tastes in music to viral YouTube videos, after the awkward fumbling for the check, the walk to the curb, the stilted hug-turned-air-kiss-turned-forehead bump, after the goodbyes—every first date leaves one nagging question:

Will you ever hear from them again?

The dating game is an imperfect market: you may dazzle your date with your wit and mega-watt smile only to never hear from them again. Or you may look forward to meeting a match from a dating site all week, only to find that, although your date portrayed himself accurately online, you’re disappointed when you meet him offline.

People are complex, and the reasons why we do or don’t hit it off with one another can be unpredictable. But as with any complex market, there are some underlying principles to dating, and certain commonalities that are exposed when you look beyond your own experiences.

We thought we’d examine the theories put forward by economists as to how dating should work, and then compare that to the reality. Hopefully, we can illuminate some reasons why first dates go so wrong, so often—and maybe bring about a few more second dates in the process.

An Introduction to Economic Dating Theory

Dating as an economic field of study dates back to Gary Becker’s famous 1973 two-part article “A Theory of Marriage.” Becker envisioned society as a massive cocktail party with men and women as rational players trying to optimize their own mate selection. His analysis predicted an outcome based on “positive assortative matching,” with men and women pairing off with partners of similar desirability.

Imagine 100 men and 100 women, each with a number from 1 to 10 on their forehead indicating their attractiveness. In the great cocktail party of life, if you’re a 9 or a 10, people will immediately surround you and vie for your attention. When you’re fighting off suitors just to get to the bar, it signals that you are in-demand, heightening expectations and making you less likely to “settle” for, say, a four.

Similarly, if people cringe and run away when you approach them, you’ll start lowering your expectations, and maybe drown your sorrows with a few tequila shots. After a series of interactions in which the hot commodities become more aware of their hotness and everyone else… comes to grip with reality, an equilibrium will be reached, with 4’s paired with other 4’s, 6’s with 6’s, and those obnoxious 10’s coupled up and making out in the photo booth.

In more recent studies, researchers have run trials in “random matching test environments,” known to laymen as speed dating events, yielding results that support certain dating stereotypes (on average, women that score higher in attractiveness get more dates) and refute other well-worn clichés (for example, there was no evidence of a White male preference for East Asian women).

These experiments also revealed gender differences among daters, the caveat being, of course, that these dates were all of 4-minutes long. Gathering data from more than 400 speed date matches, researchers found that male daters placed a far greater emphasis on appearance than female daters did. In contrast, intelligence ratings were more than twice as important in predicting women’s choices as men’s.

The study claimed that men did, however, show a preference for more intelligent women—up to a point. Men preferred smarter women, but avoided women who they perceived as more intelligent than themselves. The same pattern emerged for career ambition.

Our Experiment: Exposing Dating Inefficiencies

In the real dating scene, outside of these controlled experiments and thought exercises, matches are neither random nor frictionless; we find our first dates based on who we happen to meet at bars or whose profiles we stumble across on dating apps. It is an imperfect market at best, and the unpredictable, oft-confounding outcomes of first dates have served as the raw material for many a self-help book, romantic comedy, and Carrie Bradshaw quote.

As the author is a straight female, she decided to investigate the dating landscape through the eyes of straight, single guys—at first, admittedly, to explain some of the baffling behavior exhibited by guys her age. But in the process, she found the data revealed some larger truths that, regardless of gender or orientation, might be keeping people single, longer.

We asked 51 straight, young professional men based largely in San Francisco and New York everything from how often they date to exactly when they knew their last failed date was going south.

The most common way our survey respondents found dates was through their extended social networks: 78% of men surveyed frequently date friends of friends and 40% had asked out a friend before. Over 1/3 of the men we surveyed also find dates online—including, unexpectedly, one from Craigslist’s Missed Connections.

While the survey yielded some hilarious anecdotes that the author would happily share over drinks, it also highlighted several dating inefficiencies that, combined with behavioral economics, might help explain your last bad date.

Dating Inefficiency #1: First dates are optimized – for boredom

Over 66% of the men we spoke with chose “she was boring” as one of the top three dating turn-offs they encounter, making it the biggest turn-off on our list.

This outcome may seem surprising given that first dates are often designed to cover the basics and stick to neutral territory.

But according to behavioral economist Dan Ariely, this “don’t ruffle feathers” model of first dates is exactly the problem. As he writes, “when going on a first date, we try to achieve a delicate balance between expressing ourselves, learning about the other person, but also not offending anyone—favoring friendly over controversial—even at the risk of sounding dull.”

While not rocking the boat may seem like ideal strategy for getting a second date, Ariely argues that sticking to neutral topics (haven’t we all been on a date where the weather was discussed ad nauseum?) creates a "bad equilibrium"—an outcome where both sides converge, but neither side is pleased with it.

In an experiment he ran with online daters, subjects were forced to eschew safe topics in their messages and only throw out probing, personally revealing questions like “How many lovers have you had?” or “Do you have any STDs?”

The result? Both sides were more satisfied with the outcome. So the next time you find yourself on a “boring” date, the solution may be to push the envelope—and converge upon a new equilibrium.

Of course, this strategy may not work for everyone. According to one survey respondent who tried to spice up a first date, “We went to a comedy show and she got offended.... as I laughed.”

Dating Inefficiency #2: We set ourselves up for disappointment

Our least surprising finding: physical attraction is an important factor for men when asking a girl out on a second date.

However, the importance of a woman’s appearance varied significantly depending on how the date came about. Appearance was the primary deal breaker in 33% of all online dates, as compared to 11% for dates organized through social circles. And according to our survey, online daters were twice as likely to rule out a second date upon first impression as compared to those who were introduced via non-virtual means.

While there are no doubt instances of “bait and switch” taking place online, some of these dates likely failed because of the human tendency to overemphasize what we want to be true when given incomplete information. Research from Rachel Greenwald, author of Have Him at Hello, indicates that the cognitive dissonance between perception and reality, and the fact that we tend to over-value loss as compared to gain, is often the root cause of why matches fail—not the reality of the girl's appearance itself. The real issue is that daters build up expectations of the other person’s attractiveness beforehand, setting themselves up for disappointment and snuffing out a potential match before it even has a chance to catch fire.

Greenwald explains that this does not just apply to appearance; daters often misconstrue vague statements such as “I’m outdoorsy” to match their own expectations of the phrase—whether that means an affinity for weekend hikes or a desire for multi-week Everest excursions. These preconceptions set people up for greater disappointment when the truth is revealed, and they feel like they’ve “lost” a trekking companion, even though all they ever had was someone to take strolls with.

These hyped-up expectations are hardly confined to our Internet-centric dating era. As F. Scott Fitzgerald writes in The Great Gatsby of Daisy and Gatsby’s long-awaited reunion, “There must have been moments even that afternoon when Daisy tumbled short of his dreams – not through her own fault, but because of the colossal vitality of his illusion.”

One can only imagine what would happen if Gatsby had a Match.com account.

Dating Inefficiency #3: Mismatched Timing

Over 20% of survey respondents cited timing as the primary reason they didn’t follow up for another date (either because they were more interested in another girl they were dating or weren’t “looking for anything” right now).

Here are a few quotes we received from survey respondents on the issue of timing:

1) “I'm not looking for a serious relationship, simply an activity partner because I have a lot of things going on in my life that I can't commit fully to a girl.” 2) “My career is morr important to me right now.” [sic] 3) “Opportunity Cost - I found out I didn't like the girl enough to give up meeting other people (specifically, people I'd already met) and so felt another date would be time wasted.”

Our survey confirmed that for many young men on the scene, filling their social calendar with dates was not a high priority. Of the 51 men we heard from, 84% identified themselves as “Casual daters” (they try to get a date on the calendar about once a month) or “Selective daters” (they only date someone who they really think they have potential with).

For many, it seems that the “opportunity cost” of dating is a large deterrent. According to an It’s Just Lunch survey of 38,912 singles, 52% of respondents felt that they were too busy to date. Combine busy schedules with a surfeit of dating choices (including the ever-replenishing well of the Internet), and it’s no wonder that many daters want to keep their options open. As one of our daters succinctly stated, “I’ve got a lot of leavin’ left to do.”

The timing problem also arises because dating markets aren’t as cleanly defined as the theoretical “cocktail party marriage market” described above. In a frictionless world, all people would be looking for the same outcome—a stable match—rather than some convoluted title. When the two parties involved can have totally different expectations of the outcome, it becomes much more complicated to match up the correct suppliers with the correct demanders. (What exactly is an “activity partner” anyways?)

If this is the case, signaling intentions beforehand may be the best way to avoid a misunderstanding. Such is the premise behind dating sites like eHarmony.com, which markets itself as the “marriage-minded” dating site and thus, attracts people who are all looking to broker in the same market. The high monthly fee ($39.95/month) also serves a signaling device, indicating a level of buy-in and commitment to finding a stable match.

A variety of services have emerged to help those looking to date in the many nebulous, interstitial phases between ‘single’ and ‘marriage-minded.’ Tinder is a popular, ‘casual’ dating app. And in the gay community, Grindr markets itself to those not necessarily concerned about commitment.

For many daters, defining and signalling just what they are looking for can be a major challenge. For those looking for ‘activity partners,’ might we suggest joining a tennis league?

Takeaways: Can We Solve Inefficiencies?

There are few things certain in life—death, taxes, and, we’d argue, a string of bad first dates. But hidden amidst the awkwardness, boredom and disappointment, there just might be glimmers of insight that will improve the odds.

Next time you’re on a boring date, consider shaking up the conversation and moving to a new, more interesting equilibrium with a few probing questions. But please don’t write in if your STD question does not land as intended.

If you find yourself disappointed by an online date, ask yourself whether it is really the other person or “the colossal vitality of your illusion” that’s at the root of the problem.

Or perhaps you and your date are operating in two distinct marketplaces. If you’re looking for something serious, then it might be best to signal your intentions, and in turn, attract dates who’re demandin’ what you’re supplyin’.

Finally, we’ll leave you with one reassuring piece of advice from novelist Florence King that contradicts any assortative matching theories you may harbor: “Keep dating and you will become so sick, so badly crippled, so deformed, so emotionally warped and mentally defective that you will marry anybody.”

Ain’t love grand?

Our next article looks at how Subaru created targeted ads for lesbians to gain a foothold in the American car market. To get notified when we post it → join our email list.

Priceonomics first published this article on September 19, 2013.

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