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Missed Connections

The strangest questions Amy Webb has ever seen

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Amy Webb’s Facebook page shows that, over the last couple weeks, she has been interviewed by CNN, the Guardian, 20/20, Good Morning America, Marketplace, and a slew of other media outlets, all about her book Data, a Love Story (Dutton). In the book, Webb takes the Nate Silver approach to online dating and analyzes all the available data on JDate to find the perfect man. (JDate because her man must be “Jewish, but Jew-ish. Not religious!” If specifying the ethnicity of a spouse seems a bit particular, that’s only one requirement of her very specific dream man, including “No hairless balls!” which comes in at a surprising No. 5 on her initial list.)

Webb is a lover of lists, charts, and graphs. I don’t know if she collects data on the questions she is asked by interviewers, but she told my editor that mine were the strangest she has ever encountered.

When I first wrote Webb, I received no response. Then my editor, who went to J-School with Webb (disclosure), contacted her and eventually a woman named Cheryl, the director of operations at Webbmedia* (Webb’s consulting business), got back in touch with me. She kept writing to change the time of our interview—I assumed because better offers came around.

I suggested that I would simply write a book review.

“Amy would prefer some Q&A over e-mail. Wanna shoot for that? Totally doable.”

Figuring this might be a nice lesson in the difficulties of online communication, I sent a series of six questions, to which I received no response. But my editor did. Webb wrote about me, saying, “He’s said that he’s writing a story with or without my input, which seems really strange.” And later: “I’ll be honest, it was probably the strangest list of questions I’ve ever seen.”

So there we were, sunk in the wilds of online communication.

As we meet Webb in the introduction to her book, she is going through a breakup with a man who once seemed perfect. Then again, she had been desperate. Webb flashes back, telling us that she was working for Newsweek in Japan, “covering pop culture and tech trends.” But she “was growing lonely and increasingly skeptical of my ability to land a great husband while living overseas, so I’d made a tough decision to move back to the States.”

In her flurry of media appearances, Webb touts the book as one which empowers women to go after what they want, but this doesn’t seem to be a particularly empowering proposition—put aside your career and move back home so you can find a man.

This prompted one of those “strange” questions I asked Amy Webb: What would you say to feminists who would criticize this all-consuming desire to find a man?

As it happens, she does meet a man—the one she is leaving in the intro—and he sweeps her off her feet. She moves to Philadelphia and is miserable and finally leaves. Her mom and her sister prod her to try online dating. She’s getting older, after all. She has some terrible dates and starts sneaking off to the bathroom with her laptop to give real-time updates of their annoying qualities. Finally, one night, with red wine and cigarettes, she has a breakthrough.

That moment, the turning point of the book, resembles the crucial scene in the first season of Showtime’s Homeland where brilliant but bipolar CIA analyst Carrie Mathison goes off the deep end and color codes everything surrounding suspected American terrorist/war hero Brody—it seems crazy, but she figures it out.

It is a great moment because Webb’s narrative voice is the strongest thing in the book. “Fuck it, I thought. If I’m making a fucking list, I’m making a fucking list. I took another drink of wine out of my coffee mug and continued.”

As a narrative technique, this is quite clever, because the reader follows Webb on what is ultimately a philosophical journey of self-discovery.

This prompted another of my “strange” questions:

“I really liked the narrative voice, especially when it was vulnerable and gritty,” I wrote. “In writing the book, did you read a bunch of ‘popular,’ or ‘great’ books and collect data and create a narrator in a way similar to creating a profile? The ‘I’ in a piece of narrative nonfiction is always constructed in a certain sense. How much did your literary process mimic your profile-creating process?”

My assumption was that, even in a memoir, narrative voice is not natural, but created, and someone who spent weeks crafting an online dating profile would use at least an equal degree of craft to create a narrative voice. She assumed, it seems, that I was accusing her of being phony.

“He asked me if I borrowed my narrator’s voice from another popular book . . . which kind of doesn’t make sense. It’s my voice, and it’s memoir,” she wrote my editor.

Deeper into the pit of electronic misunderstanding! But, this is precisely the journey Webb makes in her book. On her first JDate profile, she simply cut and pasted her resume, and she was shocked when no one was particularly interested in her HTML skills. She goes on to create a number of false male profiles in order to judge her competition. Using these fake profiles, she tools her own profile based on what popular people on JDate do. And the realizations are actually pretty simple: Be fun and flirty so people want to know more.

Another of my questions:

“I feel like it often takes me a great deal of labor to arrive at a simple answer: How did it take you this whole process to arrive at what the ‘popular’ people already did?” I asked. “I mean, they didn’t have the data and came to the answer. So the big question I have is: Is it the data and data collection that is the important part of the book? Or the answer it provides about the kind of profile to create?”

Finally—and I’m not giving anything away here, because it is part of the marketing of the book—she meets her dream guy, a Jew-ish ophthalmologist in Baltimore and eventually moves here. We already experienced her disastrous move to Philadelphia, where she was not happy. This prompted perhaps the strangest question Amy Webb has ever been asked.

“You aren’t particularly charitable to Philadelphia and the weekly paper where you worked. Baltimore is definitely not as glitzy as New York or Tokyo. You found the right man through the formula. When you moved here, did you apply any formula to see if it was a compatible city? Have you been disappointed with the city? Your Facebook profile still says New York, after all.”

To this she responded (to my editor): “Hey there. So I just got questions from Baynard, and I’m pretty confounded. He’s mischaracterizing much of what I wrote, and there are some inaccuracies in his questions. Example: I’ve never said that I’m from NYC on Facebook, and that was even when I was using it just after Columbia. He posits that I’m embarrassed about living in Baltimore and therefore have NYC as the town listed, which it isn’t. He also sort of accuses of me not liking Baltimore, which totally isn’t true. I’m a Baltimore lifer, and I happen to love my adopted city.”

I didn’t think I was talking to Sarah Palin, for whom any actual question is “gotcha journalism,” but that is the kind of atmosphere softball interviews like Good Morning America create. And though she has since changed it, my editor dutifully cut and pasted where her Facebook profile said she lived in New York. Is it wrong to think the author of this book about creating an online profile might take her Facebook profile seriously? I wondered.

I never got to find out, because we were still trapped in the strange Twilight Zone of missed connections and miscommunication. Amy Webb and I only actually interacted one time, when she responded to my clarifying message to Cheryl:

“Hey Baynard. So thanks for the clarification and for your interest in my book. The biggest issue is your deadline. . . there’s just no way I can make it. I’m in Dallas as I type this and am rushing to get to the airport today ahead of some meetings. Then I’m booked again solid tomorrow, then all day Saturday and Sunday for Spark Camp meetings. . . . Sorry I’m not available. Meantime, I have no idea why FB says NYC, other than it must have auto located me a while back and I didn’t look to change it. It’s not a trick, just a weird geolocation quirk of FB.”

On the internet, Webb did not come across as a particularly likeable person—and, I daresay, neither did I—but this makes the book’s guidance all the more necessary—even if you’re not interested in finding a man.

*In an earlier version of this story we characterized Cheryl as the director of communications at Webb Media, rather than the director of operations at Webbmedia and mistakenly placed a colon in the book's title. City Paper regrets the errors.

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