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  • So my name is Amy Webb,

  • and a few years ago I found myself at the end

  • of yet another fantastic relationship

  • that came burning down in a spectacular fashion.

  • And I thought, you know, what's wrong with me?

  • I don't understand why this keeps happening.

  • So I asked everybody in my life

  • what they thought.

  • I turned to my grandmother,

  • who always had plenty of advice,

  • and she said, "Stop being so picky.

  • You've got to date around.

  • And most importantly,

  • true love will find you when you least expect it."

  • Now as it turns out,

  • I'm somebody who thinks a lot about data,

  • as you'll soon find.

  • I am constantly swimming in numbers

  • and formulas and charts.

  • I also have a very tight-knit family,

  • and I'm very, very close with my sister,

  • and as a result, I wanted to have

  • the same type of family when I grew up.

  • So I'm at the end of this bad breakup,

  • I'm 30 years old,

  • I figure I'm probably going to have

  • to date somebody for about six months

  • before I'm ready to get monogamous

  • and before we can sort of cohabitate,

  • and we have to have that happen for a while before we can get engaged.

  • And if I want to start having children by the time I'm 35,

  • that meant that I would have had to have been

  • on my way to marriage five years ago.

  • So that wasn't going to work.

  • If my strategy was to least-expect my way

  • into true love, then the variable that I had

  • to deal with was serendipity.

  • In short, I was trying to figure out, well,

  • what's the probability of my finding Mr. Right?

  • Well, at the time I was living in the city of Philadelphia,

  • and it's a big city, and I figured,

  • in this entire place, there are lots of possibilities.

  • So again, I started doing some math.

  • Population of Philadelphia: It has 1.5 million people.

  • I figure about half of that are men,

  • so that takes the number down to 750,000.

  • I'm looking for a guy between the ages of 30 and 36,

  • which was only four percent of the population,

  • so now I'm dealing with the possibility of 30,000 men.

  • I was looking for somebody who was Jewish,

  • because that's what I am and that was important to me.

  • That's only 2.3 percent of the population.

  • I figure I'm attracted to maybe one out of 10

  • of those men,

  • and there was no way I was going

  • to deal with somebody who was an avid golfer.

  • So that basically meant there were 35 men for me

  • that I could possibly date

  • in the entire city of Philadelphia.

  • In the meantime, my very large Jewish family

  • was already all married and well on their way

  • to having lots and lots of children,

  • and I felt like I was under tremendous peer pressure

  • to get my life going already.

  • So if I have two possible strategies at this point

  • I'm sort of figuring out.

  • One, I can take my grandmother's advice

  • and sort of least-expect my way

  • into maybe bumping into the one

  • out of 35 possible men in the entire

  • 1.5 million-person city of Philadelphia,

  • or I could try online dating.

  • Now, I like the idea of online dating,

  • because it's predicated on an algorithm,

  • and that's really just a simple way of saying

  • I've got a problem, I'm going to use some data,

  • run it through a system

  • and get to a solution.

  • So online dating is the second most popular way

  • that people now meet each other,

  • but as it turns out, algorithms have been around

  • for thousands of years in almost every culture.

  • In fact, in Judaism, there were matchmakers

  • a long time ago, and though

  • they didn't have an explicit algorithm per se,

  • they definitely were running through formulas in their heads,

  • like, is the girl going to like the boy?

  • Are the families going to get along?

  • What's the rabbi going to say?

  • Are they going to start having children right away?

  • And the matchmaker would sort of think through all of this,

  • put two people together, and that would be the end of it.

  • So in my case, I thought,

  • well, will data and an algorithm

  • lead me to my Prince Charming?

  • So I decided to sign on.

  • Now, there was one small catch.

  • As I'm signing on to the various dating websites,

  • as it happens, I was really, really busy.

  • But that actually wasn't the biggest problem.

  • The biggest problem is that I hate

  • filling out questionnaires of any kind,

  • and I certainly don't like questionnaires

  • that are like Cosmo quizzes.

  • So I just copied and pasted from mysumé.

  • (Laughter)

  • So in the descriptive part up top,

  • I said that I was an award-winning journalist

  • and a future thinker.

  • When I was asked about fun activities and

  • my ideal date, I said monetization

  • and fluency in Japanese.

  • I talked a lot about JavaScript.

  • So obviously this was not the best way

  • to put my most sexy foot forward.

  • But the real failure was that

  • there were plenty of men for me to date.

  • These algorithms had a sea full of men

  • that wanted to take me out on lots of dates --

  • what turned out to be truly awful dates.

  • There was this guy Steve, the I.T. guy.

  • The algorithm matched us up

  • because we share a love of gadgets,

  • we share a love of math and data and '80s music,

  • and so I agreed to go out with him.

  • So Steve the I.T. guy invited me out

  • to one of Philadelphia's white-table-cloth,

  • extremely expensive restaurants.

  • And we went in, and right off the bat,

  • our conversation really wasn't taking flight,

  • but he was ordering a lot of food.

  • In fact, he didn't even bother looking at the menu.

  • He was ordering multiple appetizers,

  • multiple entrées, for me as well,

  • and suddenly there are piles and piles of food on our table,

  • also lots and lots of bottles of wine.

  • So we're nearing the end of our conversation

  • and the end of dinner, and I've decided

  • Steve the I.T. guy and I are really just not meant for each other,

  • but we'll part ways as friends,

  • when he gets up to go to the bathroom,

  • and in the meantime the bill comes to our table.

  • And listen, I'm a modern woman.

  • I am totally down with splitting the bill.

  • But then Steve the I.T. guy didn't come back. (Gasping)

  • And that was my entire month's rent.

  • So needless to say, I was not having a good night.

  • So I run home, I call my mother, I call my sister,

  • and as I do, at the end of each one of these

  • terrible, terrible dates,

  • I regale them with the details.

  • And they say to me,

  • "Stop complaining."

  • (Laughter)

  • "You're just being too picky."

  • So I said, fine, from here on out

  • I'm only going on dates where I know

  • that there's wi-fi, and I'm bringing my laptop.

  • I'm going to shove it into my bag,

  • and I'm going to have this email template,

  • and I'm going to fill it out and collect information

  • on all these different data points during the date

  • to prove to everybody that empirically,

  • these dates really are terrible. (Laughter)

  • So I started tracking things like

  • really stupid, awkward, sexual remarks;

  • bad vocabulary;

  • the number of times a man forced me to high-five him.

  • (Laughter)

  • So I started to crunch some numbers,

  • and that allowed me to make some correlations.

  • So as it turns out,

  • for some reason, men who drink Scotch

  • reference kinky sex immediately.

  • (Laughter)

  • Well, it turns out that these

  • probably weren't bad guys.

  • There were just bad for me.

  • And as it happens, the algorithms that were setting us up,

  • they weren't bad either.

  • These algorithms were doing exactly

  • what they were designed to do,

  • which was to take our user-generated information,

  • in my case, mysumé,

  • and match it up with other people's information.

  • See, the real problem here is that,

  • while the algorithms work just fine,

  • you and I don't, when confronted

  • with blank windows where we're supposed

  • to input our information online.

  • Very few of us have the ability

  • to be totally and brutally honest with ourselves.

  • The other problem is that these websites are asking us

  • questions like, are you a dog person or a cat person?

  • Do you like horror films or romance films?

  • I'm not looking for a pen pal.

  • I'm looking for a husband. Right?

  • So there's a certain amount of superficiality in that data.

  • So I said fine, I've got a new plan.

  • I'm going to keep using these online dating sites,

  • but I'm going to treat them as databases,

  • and rather than waiting for an algorithm to set me up,

  • I think I'm going to try reverse-engineering this entire system.

  • So knowing that there was superficial data

  • that was being used to match me up with other people,

  • I decided instead to ask my own questions.

  • What was every single possible thing

  • that I could think of that I was looking for in a mate?

  • So I started writing and writing and writing,

  • and at the end, I had amassed

  • 72 different data points.

  • I wanted somebody was Jew...ish,

  • so I was looking for somebody who had the same

  • background and thoughts on our culture,

  • but wasn't going to force me to go to shul

  • every Friday and Saturday.

  • I wanted somebody who worked hard,

  • because work for me is extremely important,

  • but not too hard.

  • For me, the hobbies that I have

  • are really just new work projects that I've launched.

  • I also wanted somebody who not only wanted two children,

  • but was going to have the same attitude toward parenting that I do,

  • so somebody who was going to be totally okay

  • with forcing our child to start taking piano lessons at age three,

  • and also maybe computer science classes

  • if we could wrangle it.

  • So things like that, but I also wanted somebody

  • who would go to far-flung, exotic places,

  • like Petra, Jordan.

  • I also wanted somebody who would weigh

  • 20 pounds more than me at all times,

  • regardless of what I weighed.

  • (Laughter)

  • So I now have these 72 different data points,

  • which, to be fair, is a lot.

  • So what I did was, I went through

  • and I prioritized that list.

  • I broke it into a top tier and a second tier of points,

  • and I ranked everything starting at 100

  • and going all the way down to 91,

  • and listing things like I was looking for somebody who was really smart,

  • who would challenge and stimulate me,

  • and balancing that with a second tier

  • and a second set of points.

  • These things were also important to me

  • but not necessarily deal-breakers.

  • So once I had all this done,

  • I then built a scoring system,

  • because what I wanted to do

  • was to sort of mathematically calculate