When I first met her, there were no questions for Amy Dickinson. No "I slept with my ex-boyfriend two days before his wedding—what should I do?" No "Should I leave my wife for my high school sweetheart?" Not even an inquiry about whether it's appropriate to breast-feed during a cocktail party. But that's only because she hadn't made it to her office yet. It was still early in the morning—a few minutes before 8:00 A.M. on a bright, temperate day in late October. Dickinson, an attractive forty-five-year-old woman—she somehow looks like a combination of Mary Tyler Moore and Pat Benatar—was sitting on the top step of Chicago's Field Museum, reading the paper, her paper, the Chicago Tribune.
Late the night before, reporters at the rival Chicago Sun-Times had come to terms with management just in time to avert an expected strike. A few days later Northwestern would upset Purdue in Evanston at homecoming. Both were good things. But the pleasant feelings they induced would not last. Soon the city's harsh winds and early sunsets would drive everyone indoors, away from dinner parties and scheduled drinks—away from one another, really, and into near hibernation. And this would be the time when Chicago—and other places all across the country—would really need Amy Dickinson. Because inside their too small apartments or too large colonials people would begin to question their motivations for staying with one another, or to suspect that their adoptive fathers never gave a damn, or to yearn for reunion with their estranged children, long-lost lovers, alienated friends. They would wonder if they should tell their spouses about that fleeting infidelity at a motel near the Minneapolis airport fifteen years before.
It may have been too early in the day for Dickinson to be sifting through her readers' questions, but it was not too early to check out her competition. Dickinson became the author of the column "Ask Amy" in July of 2003, when the Tribune gave her the newsprint real estate that had long belonged to Eppie Lederer, known to Western civilization as Ann Landers. Today she read her own column first ("just to make sure we're still in business, if you know what I mean"), and then flipped to the back of the Tribune to read "Dear Abby," the column of her nearest rival (which is written by Jeanne Phillips, who happens to be the daughter of Eppie Lederer's twin sister, Popo Phillips, its original author).
For two columnists plying the same trade, Dickinson and Phillips could hardly be more different. On this day Dickinson told a middle-aged married woman that it's okay to have crushes on other men—"enjoy but don't indulge"—and admitted to having had a dream ("it wasn't a sex dream") about Dr. Phil. She consoled the mother of an unwed pregnant eighteen-year-old, telling her it was all right to throw the girl a baby shower. Hell, Dickinson wrote, "that horse has left the barn." In response to "Perfect Wedding in Arizona," who was not on speaking terms with most of her family, Dickinson sidestepped an etiquette question about whether Perfect should be forced to invite people she didn't want to and pointed out bluntly that not speaking to whole groups of her kin was a sign that she didn't "'do' family well." Phillips, meanwhile, fielded a question about how many days' notice a family member should give before a visit, and let a reader from Georgia share a random act of kindness she had benefited from.
After concluding that she had bested Phillips that morning, Dickinson and I wandered into the main hall of the Field Museum. The CNN anchors Bill Hemmer and Soledad O'Brien were there taping their show, American Morning, which on this morning would feature an interview with the author of "Ask Amy." Dickinson tracked down a producer, who ushered her to makeup. Her eyes firmly shut, and clutching the edges of the makeup chair like an astronaut re-entering the atmosphere, she asked the makeup artist to teach her how to apply eyeliner—something that, she admitted, was among many things she should have learned when she was fifteen. Of course, when she was fifteen she was busy with field hockey and cheerleading and plays—not to mention with trying to hold her family together; three years earlier her father had walked out into the night, never to return. Someone asked her what she was going to be speaking about on the show. "Well, I write the advice column for the Trib," Dickinson said. "So, hopefully, I'll just straighten them out and send them on their way."
Trying to straighten out people's lives while making a name for herself in the shadow of the woman who defined the form—this is the task Dickinson has taken on in her brief tenure as the newest member of the oddest species in American journalism. Unlike Eppie Lederer, however, she does not have the benefit of a stable newspaper-reading audience; instead she has the daunting task of developing a new readership—she currently reaches several million readers—in a little over a hundred papers, including the Los Angeles Times, The Washington Post, and Newsday.
For most of the past half century Eppie Lederer's Ann Landers was recognized as the unquestioned doyenne of the field, but the advice-column format existed long before Lederer became, as her last Tribune editor, Rick Kogan, put it in the title of his biography of her, America's Mom. Writing as Dorothy Dix, Elizabeth Meriwether Gilmer counseled American newspaper readers through the Great Depression, two world wars, and the dawn of the Cold War in a column that ran from 1895 until shortly before her death, in 1951. Writing as Beatrice Fairfax, Marie Manning doled out advice to millions of regular readers—and was immortalized by a line in the 1930 George and Ira Gershwin musical Girl Crazy: "Beatrice Fairfax—don't you dare / Ever tell me he will care."