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Data, A Love Story: How I Gamed Dating To Meet My Match Excerpt

01/30/2013 10:55 am ET | Updated Apr 01, 2013

The following is an excerpt from Amy Webb's, Data, A Love Story: How I Gamed Dating to Meet My Match.

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?

I wondered how JewishDoc1000 might perceive the Yozora version of me, based on the original JDate profile I'd posted and within the context of all these other women. I sat down, grabbed my notepad, and started sketching.

On the right, I wrote my name and copied down the most prominent highlights from my profile.

On the left, I wrote HottieDC and listed the major points of her profile.

As I looked at both sides of my paper, it didn't take long to see how what I'd written might be off-putting.

And then I considered my profile photos. I'd used three.

I'd made a conscious decision to select these three photos. In the first, I was snuggling our family dog, which I thought made me seem like an easygoing pet lover. But now, looking at that photo on the JDate page, all I could see was Bailey's dirty, strange fur and wonder what it was attached to. I knew the second wasn't flattering at all, but it showed me at work, speaking at a prestigious conference to a huge crowd of people. In the third, I was still in grad school at Columbia University, standing next to the Alma Mater statue. I'd done my makeup well that day and my skin looked really radiant. I'd received a few compliments from strangers, and one woman even asked me where I got my facials. Looking now with a fresh perspective, I realized that my photos were yet another detriment.

I went deeper into JDate, clicking beyond the popular profiles and through to pages 19, 20, and 21, where the listings become more random. As horrible as I knew my photos were, I could now see that my profile wasn't as awful as some of the others. One woman blathered on and on about how important fitness was to her. She was attractive, maybe a little too muscular. She listed thirty-seven different activities that she participated in regularly: kayaking, water polo, water aerobics, spinning, step aerobics, interval training. She said that her goal was to run ten marathons that year. Obviously being active was important to her, and any partner would have to be fit too. But the detail and breadth to which she described everything had to have been off-putting to anyone who wasn't some kind of Olympic athlete.

Another woman kept her profile very succinct: I'm single. I'm not a weirdo. I have a steady job. I'm looking for someone I won't be embarrassed to introduce to my friends.

Saying that she wants a man who won't embarrass her sounded really aggressive and negative to me. And the very fact that she said she wasn't a weirdo made her sound like... kind of a weirdo.
I could see that vast majority of online daters don't agonize over building their profiles as much as they should. I certainly didn't. I hastily copied and pasted content from my résumé, assuming that what really mattered was not some digital profile, but the first few interactions.

While I'd included way too much specific, sterile information, others had written the minimum number of characters just to fill space and had relied instead on what they thought were great photos.

But even for really attractive women, photos were problematic. Many women uploaded photos with a phantom shoulder in view. Whose shoulder was it? A recent ex? A current boyfriend? It was rarely someone's brother or best friend. Some photos were grainy and dark, so it was difficult to see what the woman really looked like. There were disasters too: photos that were obviously really old, drunk photos, and photos that looked like they were bad outtakes from a Maxim shoot.

That said, at least slutty, cheesy Maxim photo women seemed like they were ready for fun.

I looked at HottieDC's profile again. She had uploaded five uniform photos. In each, she was standing at a slight angle and looking straight at the lens. She wasn't drunk. There were no furry animals or other people's body parts in the frame. Her smile didn't seem forced. In fact, I got the feeling that she'd been laughing just before the photo was taken. Her hair and makeup didn't look overdone, but she had definitely spent time on both. She was showing skin -- her décolletage and shoulders -- and each photo was cropped such that I could see just enough of her arms to assume that she also had beautiful hands and well-manicured nails. Really, the only difference in HottieDC's photos was the color of camisole she was wearing in each. She could have been a catalogue model, but one that seemed friendly and approachable enough to ask out to dinner.

I compared my photos to HottieDC's, EaglesFan32B's, and some of the other photos I saw on JDate.

There was absolutely no competition. I'd been bested by HottieDC and all the others right and good. I'd thrown my JDate profile together quickly in between work meetings because I wanted to see the men on the site. I hadn't planned a strategy for my profile. Forget strategy -- I was irritated by the whole profile-building process, seeing it as an obstacle to just meeting the men that I'd want to date.

It seemed strange now, that I'd just slap together my online dating profile, when I'd spent days agonizing over my résumé, tweaking and massaging it to land the perfect job. Sometimes I could read, edit, and reread email messages for an hour before sending them. Yet here I was, husband hunting and armed with only a handful of half-assed bullet points and what was one of the stranger assortments of photos on JDate. I hadn't stopped to consider how badly I was representing myself during that critically important first-impression stage. If JewishDoc1000 saw what I'd written, he wouldn't want to date me. For that matter, neither would the real JewishDoc57.

HottieDC's profile may have seemed insincere and shallow to me, but then I thought about all the other popular profiles I'd viewed. Were these women really that shallow, or did they instead reveal just enough information to pique interest? Maybe HottieDC was smarter than I was giving her credit for. Online, she was definitely more enticing than me. She was open, less competitive, and more eager to date.

© Amy Webb 2013, reprinted with permission of Dutton, member of Penguin Group U.S.A.

AMY WEBB is an award-winning journalist who wrote for Newsweek, The Wall Street Journal, and other publications before founding Webbmedia Group, a digital-strategy consultancy that works with Fortune 500 companies, major media companies and foundations, the government, and others. She lives with her family in Baltimore, Maryland.