Review: Data, a Love Story, Amy Webb

Dating, for most people, is a sport. For Amy Webb, dating is, or rather was, torture–until she collected sufficient data to game the system. (Yes, you read that correctly.) Webb tells her story in Data, a Love Story: How I Gamed Online Dating to Meet My Match.

Data, a Love Story, Amy Webb

Data, a Love Story, Amy Webb

Webb’s dating woes will be familiar to many readers. Fresh out of a long term relationship, Webb, circa 2005, was ready to “settle down.” The messy end of Webb’s relationship, coupled with her extreme Type A personality and her mother’s diagnosis with a terminal illness created a sense of desperation: She was 30,  starting her own business, and living in a city (Philly) without social support. Under duress from her mom and sister, Webb logged into Match, eHarmony, and JDate. And then her real misfortunes began.

Webb describes a series of disastrous dates, ultimately culminating in one so spectacularly disappointing that it inspired her breakthrough: Drawing on her experience as a journalist and digital consultant, Webb created a profile of the man she was seeking, and collected (lots of) data to improve her chances of finding him. It will not surprise readers to find out that Webb succeeded.

What is significant about Data, a Love Story is not the end result, but the lessons Webb (and the reader) learns along the way. In other words, it’s about the journey, not the destination. Yes, Webb meets her match, and she accomplishes it on her terms, but there is a sense of growth as the story proceeds. Webb is competitive and driven, and much of the first half, or even three quarters, of the book reads as if she has a lot to prove. By the end of the book, the reader has the definite impression that Webb has become more secure in herself. Or perhaps, mission accomplished, she mellowed out.

Webb’s tactics will seem intense to most readers. Driven to succeed, Webb creates a scoring system for her ideal mate; she will go on a date with no man who scores under 700. But Webb doesn’t stop there. Realizing that her profile is weak–she copied and pasted her resume into it–Webb sets about determining what might make her a stronger candidate. In particular, she needs to become one of the “popular” girls, one of those profiles that receive lots of clicks and are featured on the landing page. In order to “compete” with other female users, Webb must understand what makes them so desirable. She needs to study their profiles and the ways in which they interact with men. It’s here that things get dodgy: Webb creates 10 (10!!!) male profiles with which to interact with female users, ultimately creating a data set that tells her ideal profile length, how long she should wait before responding to a message, and how much skin to expose in her pictures.

I confess that I was troubled by Webb’s actions, as she cavalierly experimented with human subjects. Webb is quick to point out that she established from the outset certain rules to protect the women with whom she was interacting, such as a three message maximum exchange, never agreeing to meet, and so on. Webb’s goal was not to toy with people’s emotions, but to collect the data she needed to improve her search for “Mr. Right.” It appears that Webb’s safeguards worked; she doesn’t report any hurt feelings on the part of the women she studied. Still, there is something not quite wholesome about her actions here. Consider Webb’s description of women who write profiles that are too long: They are either too openly ambitious, or they have emotional problems. She provides an example of each (I assume that she wrote these herself, based on her research), but she describes the latter as “horrible.” That’s awfully judgmental for someone who approaches dating with spreadsheets and whiteboards.

If Webb’s methods are fascinating, and her description of them icky, the last two chapters of the book are vindication: Utilizing her research, Webb constructs her “super profile,” and following the rules she established at the outset, she finds her man. Webb, by this point of her story, has grown into herself, and is more genuinely likable than she was earlier in the book. (Admittedly, she was coming out of a failed relationship.) Readers put off by Webb’s “research methods” will find themselves cheering her on as she finally meets her dream man.

Data, a Love Story is one woman’s story of online dating. Webb is a talented writer and storyteller, and her descriptions of her first dates are quite funny. Some readers may find themselves put off by Webb’s sometimes self-important posturing (I am a successful business woman. I need to date a doctor or a lawyer. I cannot date anyone who is an “aspiring” anything.), but they should remember that this is her story. Webb gives herself permission to describe her perfect mate, a process that requires 75 bullet points: Good for her. Webb’s methods may not always have been the most savory, but, ultimately, no one was hurt, she found her man, and readers got a good story out of it. Recommended for readers who enjoy romantic comedies (this could definitely be a movie…) and those tenacious enough (like me) to consider the applications of data analysis to topics as odd as online dating.

For a more scientific, but still very readable, take on information and data, see Uncharted: Big Data as a Lens on Human Culture.


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