Amy Webb heads the digital strategy house Webbmedia Group, and is a founder of the SparkCamp discussion series. She’s the author of “Data: A Love Story.”
Amy Webb – Digital strategist
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 4% 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 my résumé.
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 IT 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 IT 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.