
Stop it. Just stop it. There are various theories out there about when you should stop dating because you’ve seen enough and just choose the best of what you have available already to settle down. One of these is the optimal stopping theory from mathematics, which has given rise to the 37% rule. This rule suggests that after seeing 37% of what you are going to see, you have enough information to decide. But is this rule even close to being 100% accurate?
The 37 % Rule Comes From Optimal Stopping Theory
Dating may not be a “simple” problem. But the optimal stopping theory would cast it as a “sample” one. Before you start dating, you have no clue of what’s really out there without having enough of a real-world sample to tell. Advertising, rom-coms, and social media may tell you that there’s a Prince or Princess Charming out there for you. But once you really start dating to get a sample, you may find that isn’t the case.
At some point, though, you may desire some kind of stopping point. After all, you can’t possibly date every available person in the world. And you may have certain life goals that are time-sensitive. An early goal of dating then is to have a large enough sample to at least tell you what to realistically expect. That sample can then help calibrate your expectations and tell you when you’ve finally met someone who might be as good as it gets so that you can finally settle down.
Optimal stopping theory sets this sample size at 37% of the total population of interest based on mathematical calculations. It suggests that if you have to choose from 100 different possible options, you should sample and simply observe 37 before you can know enough about what to choose going forward. That first 37 simply serve as your calibration sample. So, the next time you find something as good as or better than the best in the first 37%, optimal stopping theory says choose it. That’s because any further searching will offer diminishing returns and will have a low probability of identifying something better.
How to Calculate the 37%
Having your dating days numbered in such a manner may sound simple in theory but can be complex in practice. For example, what number should you multiply the 37% with to get your stopping number? It isn’t going to be the total number of available people on Earth since that would still yield a number in the hundreds of millions. And you probably don’t have enough smooth lines or outfits to go on so many dates.
One suggestion has been to take the total number of dates that you can realistically go on over a selected period of time. Say that’s one per week over the course of a year. Excluding major holiday weeks like Groundhog’s Day, that could mean a total of 50 dates. Multiplying that by 37% would yield roughly 19 dates as your calibration sample. So if you’ve gone on 19 dates without allowing them to progress any further, you now have a comparison sample for the 20th date and beyond.
Another suggestion has been to simply multiply the 37% by the amount of time you want to allot to finding your partner. Say that’s a decade. Then the first three years, eight months, and 12 days would be simply your calibration sample. The 13th day of the ninth month is then when you enter the selection phase.
Problems With the 37% Rule
As can be seen, calculating the 37% isn’t exactly 100% straightforward. Neither is counting the number of dates. Unless you spend your days inside a cinderblock cell, emerging only for dates, you will be presumably encountering other people in is-it-really-a-date-or-not settings that can help you calibrate expectations as well. So the questions are what exactly counts toward the first 37% and how much variability and uncertainty might there be in the math?
Moreover, it is difficult to predict when the right fit for you may happen to wander into your life. What if that comes way before you reach the 37% mark or way after you think you’ve gone through 100% already? This 37% rule could torpedo the whole high school and college sweethearts thing.
This 37% dating rule also overlooks other things that happen a huge percentage of the time. You, your understanding of yourself, your life circumstances, and, thus, your dating pool and preferences are highly likely to change over time, especially before you truly know yourself. My naive and misguided dating attempts in my 20s, for example, left me with a skewed sample that didn’t match my true self. And a comedian once joked if he had met his longtime wife today, he probably wouldn’t have asked for a second date.
How to Use the 37% Rule
Therefore, the best way to employ the 37% rule is how you should handle many so-called dating rules: loosely. Not loosely in a everyone-come-and-get-it manner. But loosely in that rather than a hard-and-fast rule to be followed closely, it can instead be reminder of some general principles.
One of these principles is to give yourself enough time to learn about what’s out there before diving into a lifelong commitment. The second principle is the opposite. Don’t forever be thinking that something else better might come along. Don’t keep monkey-barring, which I’ve described previously in my post, “A Funny Bone to Pick.” If you’ve already found a person who seems to be a very good fit, you might want to commit. That’s assuming that you are capable of committing to anyone.
This doesn’t mean that math can’t be used to describe different things around us. The math does have to be complex enough, though, to match all of the real-life complexity and factors involved. When the math employed is a little too simple, things just won’t add up and existing problems could multiply.

