‘Data, A Love Story’ and ‘Love in the Time of Algorithms’

“Have you tried online dating?”

It’s impossible to be a single woman of a certain age — or, perhaps these days, any age — and not to have received that unoriginal, if well-intentioned, advice. Even my cousin Minna, who is in her 80s, had a six-decade-long marriage, and barely uses e-mail, made the suggestion. (Et tu, Minna?) To be fair, her daughter had found her second husband online, so Minna was something of an expert.

So, too, are Dan Slater and Amy Webb, both members of a generation that is at home online. In their new books, they take readers behind the scenes of Internet matchmaking, illuminating both its lures and its limitations.

Webb’s “Data, A Love Story: How I Gamed Online Dating to Meet My Match’’ is the more personal and slighter book, a combination of memoir and “how-to” that provides a few hours of mild entertainment.

Webb is a mostly sympathetic, if somewhat offbeat protagonist. She works as a Japanese-speaking Asia correspondent for Newsweek before following an off-line love to Philadelphia. There she takes an unsatisfying job as a reporter for a city weekly. Soon enough, her relationship implodes (the guy cheats on her), and her job ends. Meanwhile, to up the ante, Webb’s mother, dying of cancer in Chicago, is fixated on her 30-year-old daughter’s finding a mate. Talk about pressure.

So Webb, now a digital strategy consultant, turns to online dating — trying out eHarmony, Match.com, and JDate, which caters to Jewish singles.

Her initial dates, undertaken with limited vetting, are “comically bad.” One guy insists on ordering expensive wine and sticks her with the bill; another seems enticing, until his wife calls. Online dating, she begins to think (as I do), “only made it easier to meet a whole bunch of wrong men, the kind who lied in their profiles or who had major character faults.”

Then, she decides to apply math. To aid in her quest, Webb thinks deeply about what she wants in a man — never a bad idea — and develops a detailed, multi-tiered rating system in which she awards points for each criterion that a prospective date fulfills.

Let’s establish that Webb is hardly a typical young woman. The ordeal of shopping for a decent outfit or two for her online photos proves so daunting that she ends up crumpled on the floor of a dressing room, in tears. She has to call her sister, whom she relies on obsessively, for long-distance help. The sister then phones the saleswomen at the store, who hasten to Webb’s rescue.

By contrast, inventing 10 distinct online male personas as a ploy to understand the “dos” and “don’ts” of JDate is a snap for her. It’s a bizarre and time-consuming experiment that seems at least vaguely unethical, even though she limits contact with the women she meets online to a few messages.

Most of what Webb learns from her testing turns out to be fairly obvious. No, you should not post your resume, listing your language and tech skills, as your profile. You should appear fun-loving and easy to please. And, yes, it’s a good idea to dress well, apply makeup, and show some cleavage.

What it ultimately takes for Webb to meet her true love online, along with getting to know herself and the system better, is to expand her search beyond Philly. Still, she almost ruins a promising encounter with a Baltimorean when she chooses, as their first date, a visit to the Franklin Institute’s “Body Worlds” show, with its anatomically correct plastic bodies. Her companion gets sick when he sees the split testicles. From there, the relationship can only improve — enough so that Webb gets her fairy tale, and her book.

Slater, a former Wall Street Journal reporter, begins the nicely titled “Love in the Time of Algorithms: What Technology Does to Meeting and Mating” with a personal anecdote — about taking an online date to an online dating conference.

But his agenda is more ambitious than Webb’s. He offers an account of the history and evolution of online dating, explores its permutations, and hazards some guesses about its impact on relationships in the 21st century.

Along the way, Slater manages to tell intriguing stories and to take us places we might not normally go — among them, a romance tour to Medellin, Columbia, sponsored by the online dating service Amo Latina. It’s fascinating to watch a group of exceedingly awkward American men pursue young, often impoverished Latin beauties who they inexplicably think will prove less mercenary than women back home.

When it comes to ventures like this, Slater makes it clear where he stands — above it all. Neither is he particularly kind to the pseudonymous Alexis, a benighted young woman whose dating roller-coaster he chronicles in detail. Alexis thinks at first that her ideal mate must love the rock band Phish and posts way too much information about her dates on a social-networking site called Phantasy Tour.

There’s a cynical edge to Slater’s book, along with considerable information: about the distinctions between free and paid sites, and searching (more like the old personal ads) vs. matching (an imperfect science at best, and probably a phony one). Slater covers niche sites (targeting demographics such as discreet, married cheaters and people with diseases and disabilities), aggregators looking to become the Kayak of Internet dating, and mobile technology’s contributions to dating on the fly. We learn about international romance scams, as well as how dating sites use inactive profiles, and even fake messaging, to attract subscribers.

Predicting the broader impacts of online dating is tougher. Slater argues that the availability of more choices via the Internet may undercut the urge to commit. By way of illustration, he gives us the case of Jacob, an average guy of no particular appeal, who is seeing five women and sleeping with three of them. It’s a strategy that, online or off, usually depends on deceit. When, in a fit of conscience, Jacob belatedly tells one woman he’s not ready for exclusivity, she angrily texts back: “Lose my number.”

Old gender divides persist. Although Alexis tends to hook up fairly quickly with men she meets online, she is still hurt when they bail, often with little explanation. An offline boyfriend criticizes Alexis for her past promiscuity even though, she notes, her numbers are no higher than his.

Back, once again, to math: Slater reports that fully one-third of America’s 90 million singles have created an online profile, and as many as one in five committed relationships may originate online.

On the other hand, data from OkCupid, a popular free site, reveal that a woman’s popularity peaks at 21, and that, at 48, men are nearly twice as sought after as women the same age. In that respect, the online romantic market resembles the offline one — an increasingly forbidding place for women in midlife seeking something beyond novelty and a few dates.

Sure, the panoply of options online can sound tempting — until you look more closely. So, sorry, Minna: For now, I’m still sitting this online dance out.

Julia M. Klein is a cultural reporter and critic and a contributing editor at Columbia Journalism Review.