Sex, Data and the Single Woman: Review of “Data, A Love Story”

Valentines image by Vickie Bates.“Where were the soul mates we were promised on all the websites and in the commercials now playing on TV?,” wondered Amy Webb after too many dates with men who high-fived her and lied about their jobs and marital status.

Returning home after the worst date of her life, Webb opened a bottle of wine, grabbed her computer and pulled an all-nighter, analyzing the algorithms of online dating sites and her own heart.

She wrote a list of traits she wanted in her ideal man that was 72 items long and vowed to “exhaustively” vet potential suitors before going on a date.

Her sister warned her against such a detailed approach: “Trying to find a husband who fits the exact list of what you want is going to be like looking for a needle in a haystack.”

Webb responded: “It’s dead easy to find the needle. You hack the haystack.”

But, her list was just the start. After designing Mr. Right, Webb realized she needed to understand her competition before she could win the guy. And that’s when lightning struck.

“It was a simple, obvious solution…I needed to outperform all of the possible profiles in JDate’s database. I had to know what kind of women were my competition, what they looked like, what they wrote, and how they interacted with [men]. In short, it was time to join JDate as a man.”

Webb’s just-published memoir, Data, A Love Story: How I Gamed Online Dating to Meet My Match, explains how her love of numbers and sticking to a system landed her the man of her dreams. The book also takes a humorous look at how men and women communicate and the best way to create a personal brand to “market” yourself to potential mates. As you can imagine, I was in communications-marketing-data geek heaven reading this.

A Method to Her Madness

Webb carefully charted everything the most popular women on dating sites were doing – from how often they used flattery to the length of their profiles, the amount of time they’d spend instant-messaging with potential dates, and the types of photos they used.

She even noted how the women described themselves and their lives. Here, for example, are the 10 words popular women used most often:

  • Fun
  • Love
  • Laid-back
  • Laugh
  • Optimistic
  • Adventure
  • Easy-going
  • Outgoing
  • Down-to-Earth
  • Pleasure

It turned out, the vaguer women were, the better. “I learned that leaving off potential unknowns at the beginning would eventually help me get further into the dating process,” Webb writes. Turns out, guys like a woman of mystery.

With data in hand, she created the ultimate profile and pictures for herself and got back in the dating game as a woman. She faithfully rated every potential match and – here’s the kicker – never went out on another bad date.

Data, A Love Story is a breezy, fascinating, non-math-intensive read for singletons who’ve found themselves at the whim of online dating algorithms. Math geeks may love it, too, but Webb kindly keeps the story of her love life moving through the main part of the memoir and saves the statistics for the appendices.

“What first lured me to online dating was the promise of using math to identify my perfect match,” Webb notes. “To me it made perfect sense that data and math could do a much better job of bringing together compatible people than hope, fate, and a few Friday night cocktails.”

It adds up, but Data, A Love Story primarily stands as a testimony to a woman who dared to declare what she really wanted and was fearless in calculating the answer that made her happy. High five, Amy Webb, high five.


If you’re in Los Angeles on Tuesday, Feb. 26, Social Media Club – LA presents a panel discussion with the heavy-hitters of online dating and social networking. They’ll be talking about going beyond creating websites and apps to generate long-term community engagement using social media and more. Copies of Data, A Love Story will be raffled to lucky winners at this event. Details here.

Read an excerpt of Data, A Love Story on Slate.

You’ll find more on Webb’s Tumblr: