FYI Book Club picks ‘Data, A Love Story’ by Amy Webb

Amy Webb
Amy Webb

Amy Webb wasn’t looking for any more bad dates. Or even pleasant dates that clearly weren’t going anywhere.

She had cast the net wide. She had perfected her bar pose. She had agreed to all manner of set-up dates. She went online: eHarmony, Match and JDate, a network for Jewish singles.

Along Webb’s funny, painful dating journey — as so many are — an impossibly romantic coupling had slowly crashed and burned. A later online match ended none too soon, with her picking up the full restaurant tab on their first and last date and him smoking an enormous joint on a park bench.

Webb’s memoir, “Data, A Love Story,” is the next selection of the FYI Book Club. The tale turns dramatically during an all-nighter when the tech-savvy, statistics-bent Webb, fueled by nicotine and wine, analyzed why online dating wasn’t working for her and how she could fix the formula.

The best-selling book with a happy ending, now out in paperback, has had two subtitles. The first was “How I Gamed Online Dating to Meet My Match” and then “How I Cracked the Code to Meet My Match.” Webb did all three: cracked the code, gamed the system and met the man she would marry.

Here are edited excerpts of our recent conversation with Webb.

Q. Your tale begins with one of those boy-meets-girl, guided-by-fate airport encounters that seemed like destiny — you and Henry. How did that not work out?

A. The way that it doesn’t work out for everybody. We both got excited about initial connections. It was in the airport in Tokyo, and at the time I was a foreign correspondent and traveling quite a bit. We met by serendipity, chance. We seemed to have everything in common at the time, a shared interest in Japanese culture, our families happened to grow up close to each other.

He had read my work: He quoted me back to me. It all added to the mystery and romance. So many people told me it was kismet: “It’s the universe telling you something.”

But what I hadn’t done was evaluate the qualities important to me in the long-term.

How did you decide to try online dating?

I was at the point where I wasn’t interested in dating. I was interested in finding the right person and being done with the dating part.

It struck me that there was a greater probability of me bumping into the right person using a database. It made more sense to me than relying on the hope and happenstance of me being out in the world and bumping into that person. Geography is limiting if you’re not using online dating. That is, you’re making an assumption that the best possible person for you is somewhere within your general vicinity, which is a ridiculous assumption to make.

But — how did you put it? — you were meeting plenty of men using the online dating sites; they were just the wrong men.

They weren’t all bad. Some of them were bad. Some were horrible people that shouldn’t be dating anybody. But, no, they weren’t all bad, they were just bad for me. That’s the problem people face with online dating. A misconception is that people using online dating sites are trying to trick you. That’s usually not the case. Rather, you’re just likely to go out with people you don’t have that spark or connection with.

Tell about your light-bulb moment, which got to the nitty-gritty of how the online dating algorithms weren’t making good matches for you.

I just kept thinking, “I’m smarter than this. Why is this not working?”

My sister has always been my go-to person, so unfortunately for her she has been on the receiving end of lots of crazy calls late at night. She’s extremely popular and has far better social skills than I do. This particular night she was at an incredible dinner party when I called to interrupt her again and again. Her advice was to make a list of what I was looking for, probably thinking it would take a long time and I wouldn’t call back for a while.

She made a reference to “Mary Poppins.” Now, it would be difficult to estimate the number of times we watched “Mary Poppins,” on VHS tape, growing up. Both of us can quote it from beginning to end without any prompting. The kids in the movie have some reflection time about getting a new nanny, and they make this list of everything they want.

So it’s in this moment that I get it. I can see the matrix.

And you make a list of how many — 72? — items about what you’re looking for in a partner. I don’t know what my question is, except OMG?

This is the way I’ve always worked. I am surrounded, literally surrounded, by lists. One whole wall of my office is a whiteboard. I may appear like a terrifying mad scientist, but it’s the way I extract ideas out of my head and into actionable form.

I realized I would have done this with any project, but this time the project was me. I made a list and prioritized it, but that wasn’t enough. I had to dissect relationships and use the list to see what didn’t work.

How would you describe this list of the things you were looking for?

It wasn’t like a superficial shopping list. I have a good idea of who I am and how I’m grounded. It wasn’t just things I needed but about the personality and characteristics of the other person that would make us work well together.

Then the research started.

I could poke around looking for that needle in a gigantic haystack, which I did. But I also was trying to position myself better on the site. I needed to do some market research.

So I created 10 male profiles for the sole purpose of data tracking.

Were these profiles of men you would be interested in meeting?

They were a way for me to collect data and study who was interested in these profiles. I needed to collect the data, crunch the numbers and see what I needed to include in my profile to attract the kind of person I was interested in. If I could have scraped all of the data from the site, to see which profiles performed best for the kind of person I was interested in dating, I would have just done that. It certainly would have been easier.

Keep in mind, it’s not that I wanted to meld myself into something else. I wanted to create a profile product that was popular. There was no lying. I didn’t misrepresent the product, which was me.

And it ended up very different from the original profile you offered on the dating sites.

When I created my first profile, I thought it was such a tedious process, so I was copying and pasting from my work bio and resume just to get it done. I didn’t even think about taking a new photo. I just picked the least bad one.

What were a few lessons you learned?

There were details to learn about the photos you use, such as how they’re cropped. It was being less specific about what I do for a living. For me professionally, there’s no single word to use like “doctor.” To really explain what I do takes a few sentences.

It can be best to shorten your profile and to create “curiosity gaps,” the way Buzzfeed and Upworthy do with their headlines. For instance, I can say I like historical fiction without mentioning specific books and movies.

None of it matters, though, if you don’t know what you want. I’m not an online dating expert and the book is not a how-to guide. It’s a memoir. The biggest lesson I learned in this process was that I had to sit down and think about what I wanted. That’s the big idea. You can optimize your profile to the nth degree and make it unbelievably competitive, but it has to be optimized for you.

You also considered how best to interact on the dating sites. What’s something you learned?

We’re surrounded by fast communication tools, and so quickly responding without really thinking first is becoming our inclination. But people who are successful at doing this online are able to mirror regular behavior, which is to say they take their time.

If you wouldn’t pick up the phone and call somebody 10 times in a row at 2 o’clock in the morning, then you shouldn’t do that digitally. But we forget.

And at the end of your process was a date with … Brian, the man you married.

It was the last first date I ever went on. At the end of our date, a long day, I really felt that not only what I did had worked, that I had figured it out, but I also really thought he was the guy. Then I had to find a way to cool my jets. Courtship still needed time, I knew.

I did show him the list of 72 things after a few dates, and I was worried it might really freak him out, that he was going to think I was nuts. And he did get freaked out, but it was because he felt like he was reading his own bio. The way he explains it, he felt like I conjured him up.

To reach Edward M. Eveld, call 816-234-4442 or send email to On Twitter @eeveld.


Age: 40

Hometown: Grew up in suburban Chicago, lives in Baltimore

Family: Husband Brian and their daughter

Education: Bachelor’s in political science from Indiana University, master’s in journalism from Columbia University, Nieman Visiting Fellow at Harvard University

Work: Founded Webbmedia Group, which advises clients on digital media and emerging technology.

Other positions include: Contributing editor and tech columnist for Inc. Magazine and “Data Mine” columnist for Slate. Her TED talk about her memoir has been viewed more than 3.5 million times.


From Amy Webb’s “Data, A Love Story: How I Cracked the Online Dating Code to Meet My Match,” published by Dutton, member of Penguin Group U.S.A.

I felt like I was back in high school all over again. Now that I was starting to reverse-engineer JDate, I realized that in my case, the opportunity to “poke” and “flirt” with gorgeous men would yield me no better results than staring at the back of Dave Peterson’s head in environmental biology class. He was the most popular kid in school and held the usual credentials: tall, muscular, good-looking, captain of the football team. Somehow I used to think that if I stared at his head and sent all of my adolescent energy his way, that he’d eventually turn around, smile back at me, and ask me to the prom. But it didn’t matter how much I stared then, or how much I poked and clicked now. Guys like Dave would always be staring at HottieDC, the thin, blond cheerleader sitting two rows up.

I took a deep breath. I’ve definitely had too much to drink, and I’m definitely amped up — but clearly I’m missing something, I thought.

I started to put what I’d seen into an equation and to work backward, assessing all of the variables. I may not be a short, Popsicle-stick woman with huge boobs, but I also wasn’t unattractive. It’s not like I’d never been approached in a bar before. In fact, I usually wound up talking to at least one new guy if I was out with friends. Before Henry, I’d dated plenty of men, and I’d rarely initiated contact. I was outgoing, I was smart, and I was funny. Online, I may not be as immediately competitive as EaglesFan32B, but that was simply because I wasn’t going to upload a photo of myself standing on the beach in a bikini.

What did all of these women share in common? I wondered. They were all very active on the site, had been favorited many times, and were highly rated profiles. Maybe it was language? I considered how they described themselves:

▪ “petite,” “adventurous,” and “fun”

▪ “addicted to lattes, smoothies, sunshine, spinning class, and cashmere sweaters”

▪ “loves to laugh all nite long”

Nothing they wrote was controversial, committed. How can you rally against laughing? Who feels politically opposed to sunshine? It seemed that the profiles were all upbeat, positive, and fairly generic. Maybe there was a secret formula the popular crowd used, possibly without even realizing it? Were these women the same way in real life? When you met them, were they enthusiastic without being overbearing? Were they agreeable, nonspecific, perpetually cheery?

It occurred to me that I’d actually had this conversation before, more than a dozen times. When a male friend would introduce me to a HottieDC or a Happy1979, I’d politely chat with her for a few minutes and then immediately find a way to escape the tedious, tired small talk. Obviously, my friends were looking to get laid — what else could they possibly want with women like that?

The answer was easy, and it was the same every time, regardless of which one of my friends it was. These women were approachable. They weren’t a challenge. They seemed easy to date. Easy to get along with. Friendly, outgoing, and fun.

It’s what I called “Cameron Diaz Syndrome.” Think about her movies, I’d say. In “There’s Something About Mary,” she played the cheery, optimistic, girl-next-door-who’s-also-a-model archetype desired by men everywhere. She loved football and was so egregiously nice she got duped into dating an Australian con man and a psychopath with a skin condition. Under no real-world circumstance would a woman this gorgeous, this successful, and this hilarious spend the majority of her time with such a sad group of misfits. But Hollywood would have us believe otherwise.

Cameron Diaz tends to play a likable, spontaneous, easy-to-date woman on screen. Hell, even in still photos of her, she seems carefree. Ready to be everyone’s best friend. She can hang with the guys but is still secure enough to spend lots of time apart when asked. Also — importantly — she’s thin, blond, and always showing skin.

The problem, of course, is that Cameron Diaz is a movie star playing a well-honed type of character. In the real world, Cameron Diaz was thirty-three and had been bouncing from man to man while gossip magazines ruminated on whether or not she’d ever get married. Even Cameron Diaz couldn’t land a committed relationship.

Were the men of JDate suffering from an acute bout of Cameron Diaz Syndrome too? I knew that while genetics played a big role in how we look, that sense of ease and quiet confidence was something that could be cultivated. Most of us — especially women — tend to undersell ourselves. We’re taught that being direct about our achievements is tantamount to bragging. And as women, we’re reminded that men aren’t interested in competing with us. That we should admire what they do overtly, but keep our accomplishments private.

I didn’t want someone who would be intimidated by who I was and what I did. Surely there was room for honesty?


The Kansas City Star partners with the Kansas City Public Library to present a “book of the moment” selection every six to eight weeks. We invite the community to read along.

Members of FYI and the library staff chose “Data, A Love Story” by Amy Webb.

If you would like to participate in a discussion of the book, email