Amy Webb (1) (1974–)

A few months ago out of a sense of boredom I hopped onto some of dating apps after a decade in a relationship. At first it went pretty well: the women I was seeing were genuine babes, and when I switched to guys to scope out the competition, well, heterosexual men are not sending their best. I'm not exactly 90s Nicolas Cage in real-life, but I'm better than those mopes. But I got about two connections for all my swiping, and the quality of the matches started going downhill. If computerized show more dating has always been a bit of a scam, even back to the Harvard-based mainframe era Operation Match, modern monetization apps are a quagmire of dark patterns. If I were a data scientist with questionable ethics (oh dang, I am), and I controlled the horizontal and vertical via the recommender system, I could do some messed up things to get desperate people to buy-in in the hopes of finding true love, never letting them find it, while providing just enough of a drip of hope to keep them swiping and spending.

Getting laid these days requires not just good l0oks, charm, and a little luck. It takes hacking your way through a hostile platform. Webb is writing about the ancient days of 2005, but the fundamentals are pretty similar. Having skimmed the reviews, a lot of the variance comes down to how much you like Webb herself, and frankly, she is just my type: an intelligent type-A neurotic Jewish woman with wide ranging interests and a few obsessions.

Saint Motel - My Type

Webb is also nuttier than my grandma's ruggelach. She's the kind of person who when starting therapy creates a dossier of all the psychological trauma she's experienced, color coded by theme, charted by year and severity, and cross-referenced. A professional futurist and spreadsheet fanatic, she doesn't do things by halves, and after a series of absolutely awful dates, she decided to tackle this problem in a data-driven way.

Step one was to envision her ideal man, brainstorming a 70 item list of the things she wanted, and then distilling those down to 10 major and 25 minor area, along with a set of dealbreakers, all of which were given numerical point values, along with a personal promise not to go out with anyone who scored too low.

Step two was to get inside the user-experience of her ideal man via what we now call catfishing. She made 10 Jdate profiles of different versions of her tall, handsome, professional match, a variety of doctors, lawyers, stockbrokers, and other professionals, and saw what kind of women messaged them. For ethical reasons and time, her interactions were minimal

Basically, the competition was a bunch of blond shiksas lying about their height; every single one of the roughly 100 women who bite her hooks was less than the American average height of 5' 4". The general vibe was a kind of Cameron Diaz girl next door, being fun and approachable without being too ambitious. Webb's current profile, with bad pictures and her insanely ambitious resume copied-pasted verbatim, looked both sad and crazy.

So, smash cut, Webb starts working out six days a week, gets a very expensive haircut, buys a whole new wardrobe, takes new photos, rewrites her profile to fit in 150 non-threatening words, and does the geek-to-glam transformation. Then she waits, chats, and meets her perfect doctor husband, and they get married and have kids and move to New York, where she runs a futurist consulting agency.

Now, Webb had a lot of advantages. She was 31, had enough spare time and cash to do a makeover, and is definitely in the top half for brains, personality, and looks (likely higher, but I'm going to draw some generous lines that more of us might fit into). And the relatively open data policies of dating websites circa 2005 made it easier for her to do her research. 18 years later, the whole field has changed, but it can still be hacked.

The biggest change is swipe-based matching. While online dating was never exactly about thoughtful analysis, these days it's entirely instinctual, decisions made in seconds. And in that very old mammalian part of our brain, guys go for looks and girls go for status. So you have to hack the other gender's swipe behavior with a visual story that communicates the right things.

And good swipes matter, because according to some reliable sources, Hinge, Tinder, and so on use a kind of collaborative filtering recommender system. Basically, you get shown people who are like the people who swiped on you, so if your profile is bad you slide down the slope from perfectly tanned people who divide their time between high profile professional life and extreme sports towards people with regrettable facial tattoos who can absolutely explain those parole violations and why their last three relationships ended in literal flames.

I really enjoyed this book, and it provided some solid background to what the other side saw. If your tastes diverge strongly from Webb's, you probably won't like it nearly as much. show less

Yep. I read it. The whole thing. In a night. Actually, I didn't read quite the whole thing. I skipped the chapter where she describes how she met her husband (but I'll read it this weekend, promise).

I came to this book after a bunch of people forwarded me her TED talk. I guess folks think this is something I should be doing. Online dating, I think, has created this idea that anyone could be unsingle if they wanted to, so if you're single, it's got to be your fault in some way. And yes, I do show more know that if I hung out on online dating sites a lot I could be unsingle pretty damned quick, but the trick is to be unsingle with someone who's good for you. And that's a lot harder.

The way Webb's mind works is fascinating. She has a deep and holy passion for spreadsheets and charts that far surpasses that of anyone I've ever met in my life. Anal does not quite describe it. You would have to be a numbers geek of the first order to spend a month drinking alcohol and smoking cigarettes while reverse-engineering the perfect profile by creating ten Perfect Partner male-profiles and interacting with the women who like them. My good fucking god. Don't get me wrong, unlike some reviewers I found it mostly endearing--she's mastered the knack of the self-deprecating semi-putdown--but am still gobsmacked that anyone put that kind of time and effort into "how to create the perfect three-sentence profile." (Says the woman who spends thirty hours sewing herself a dress.)

She bought office supplies!

I love buying office supplies, it is true, but I have never been tempted to buy colour-coded office supplies for my online dating adventures. It seems I've overlooked a fantastic excuse. Do you suppose I could justify my own fancy-pants colour-coded pens if I wrote up a 72-point list describing the perfect guy?

There were some genuine gems uncovered in her research project that you're not likely to find in the self-help genre, like "use aspirational language" and "refer to yourself as a girl," but given where she started from, I felt like she could have saved herself an awful lot of trouble by spending one of her units (term she uses to refer to 20-minute blocks of productive time) googling "dating profile" before she decided to uplaod her resume and a crappy old photo onto Match and JDate. If this is the "before," then even a minimal investment will create a much better "after" and the month-long research-binge might have been avoidable. Then again, she seems to have really enjoyed it and she got a book deal out of it, so why not?

However, it seems to me that the book differed from the TED talk in some troubling respects. The overall message was identical, but the description of the outcome was--so far as I can remember--not. In the TED talk, if I recall correctly, she talked about getting way more than 14 messages as a result of her revamped profile. Fourteen's not too shabby, but I'm sure I received more than 14 messages in a day when I was a 33-year-old single mom. Maybe JDate doesn't get the same traffic? She talks about how she was stiffed by a date who left her with a dinner bill equivalent to one month's rent, but in the book it was a $160 bill equivalent to 25% of her rent and the guy didn't leave, he just refused to pay (and then got high on a bench outside the restaurant). She said she became the most popular profile on JDate, but--unless my math brain is simply not computing the obvious in the book--how she knows this is beyond me. It's not described.

She certainly increased her own profile's visibility and popularity, which is what she was after, and she Got The Guy, so hurray! But it feels like she oversold her success. And that her success would not have been so impressive had she not started out with bullet points about her job and a bad photograph for her profile. So for those of us starting out with a good photograph and a profile about our hobbies, as the diet industry magazine ads say, Results May Not Be As Advertised.

I did like it. It was madcap and utterly unique and I do like an intelligent, ambitious, successful woman who refuses to settle. I mean, we've got western newspapers peddling editorials about how awful the Chinese government is for pressuring young women to get married by labelling them "leftovers" and telling them that if they're not married by 25 they'll be unwanted and alone their whole life, which seems unlikely given China's gender imbalance. Yet here in good old North America, we've got relationship experts telling young, educated, successful women essentially the same thing, but five years later: Not married by 30? OH MY GOD YOU'RE OVER THE HILL NO ONE WILL EVER WANT YOU YOUR EGGS HAVE SHRIVELLED UP INTO LITTLE EGG-RAISINS AND YOU WILL CRY ALONE OVER YOUR UNBORN GRANDCHILDREN YOU SELFISH STUCK-UP HARRIDAN JUST SETTLE FOR THE FIRST 'NICE' GUY WHO DOESN'T EXPECT YOU TO PUT OUT ON DATE ONE!!!!!!!!!

If you are single and female, you know what I mean.

Plus, she hated eHarmony. Hey, me too!

So it was good, it was fun, I am impressed by her math skills and I like Amy a bunch. However, I am not expecting this to revolutionize my dating life. If it does, I'll change my rating. show less

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.

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 show more 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. show less

Feeling disheartened about her lack of success in finding in the dating pool the type of man she'd want to settle down with, Amy Webb resolves to game the system, performing meticulous and intense amounts of research into the online dating world. What makes user profiles irresistible? How long should one wait before responding to a message? What types of photos are most appealing? What are the 72(!) things she's looking for in a potential husband?

I took issue with the instances where she show more deducted "points" from dates for isolated examples of poor grammar, which kind of felt like cheap shots. Some of the examples were not necessarily even incorrect: 1) 'anesthetist' is a real occupation, and 2) 'myriad of' is an acceptable use as it is both a noun and an adjective. If you are going to point out grammar flaws in others, you had better make certain your own is impeccable (spoiler: it isn't). Having said all that, as a fan of information wrangling myself I was wowed by her intense enthusiasm and intrigued and entertained by her methods and manipulation of data toward her ultimately successful end. show less