What Amy Would Do

Should you tell your spouse about that fleeting infidelity fifteen years ago? Throw a baby shower for your pregnant-out-of-wedlock daughter? Amy Dickinson, the author of the syndicated advice column "Ask Amy," is the Chicago Tribune's successor to the great Ann Landers. And she can help—as our correspondent discovered

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."

Actually, even Ann Landers existed before Eppie Lederer. The first Ann Landers was a nurse named Ruth Crowley, who wrote the column for the Chicago Sun-Times until she died, in 1955. Her death led the paper to recruit twenty-seven writers to participate in a contest for a successor. In 1955 Lederer was new to Chicago, the daughter of Jewish Russian immigrants who had settled in Sioux City, Iowa. She had dropped out of college, married Jules Lederer, a hat salesman from Detroit, and spent her first years of married life in Eau Claire, Wisconsin, becoming active in Democratic Party politics at a time when Joseph McCarthy represented the state in the Senate. With a friend's help, Lederer—who had never published a word—became contestant No. 28 in the competition, which required answering mock questions about law and religion. Displaying the chutzpah that was to make her a legend, she decided to lend credibility to her answers by seeking input from some of the highest authorities around: Justice William O. Douglas, of the Supreme Court, whom she knew from her political work, and the Reverend Theodore M. Hesburgh, who had recently become president of Notre Dame. She got the job.

While her husband built his fortune at Budget Rent-a-Car, which he founded in 1960, Lederer became, through wide syndication, a staple of the American newspaper and led a colorful, eventful life. She feuded with her twin sister (and advice-columnist competitor) for years before they reconciled late in life; she advised presidents and CEOs and socialites. She addressed people who wrote to her as "Honey" or "Bub." She wrote compassionately about homosexuality when most of society deemed it a disease or worse, and helped launch a letter-writing campaign that led Richard Nixon to dedicate $100 million to cancer research by signing the National Cancer Act, in 1971. Working with a team of assistants, she answered even many letters that she never intended to print in her column. And as her marriage dissolved (she divorced Jules in 1975 after learning of his relationship with a redheaded British nurse twenty-eight years his junior), Lederer became a fixture in Chicago's elite. She lived in a fifteen-room apartment on Lake Shore Drive, where she worked every night from eleven to three-thirty or four in the morning, banging out responses to readers on an IBM typewriter. At a time when the city's columnists—Mike Royko, Bob Greene, Irv "Kup" Kupcinet—reveled in both their success and their eccentricities, Lederer fit right in: she was known for rising at noon, and for spending evenings on the town, usually heavily made up, wearing a St. John's suit and high heels, and attended by a male companion. The occasional faux pas (the worst being a discovery in 1982 that she had recycled letters from fifteen years earlier) were forgiven. After all, who could stay mad at Eppie?

When her contract at the Sun-Times was up in 1987, Lederer was lured over to the Tribune, which gave her a six-figure salary and a suite of offices in the Tribune Tower. She rarely spent any time there, though; her limousine driver would fetch the bundles of mail and take them back to her apartment. When she did stop in, former colleagues have said, she was sometimes volatile and intemperate to those around her.

But Lederer was deeply committed to her column, and she continued to work even in her last days. When she learned that she had multiple myeloma (a cancer of the bone marrow), in January of 2002, she refused chemotherapy, and wrote the column from her bed until the pain became too great. Very few knew about her illness, and she died quietly on the afternoon of June 22, 2002, with only a caregiver at her side. Her only child, Margo Howard, did not hold a large ceremony, choosing instead a quiet gathering of sixteen people, who watched as Lederer's ashes were scattered in Lake Michigan. Many of her society friends were not among them; neither was her niece, Jeanne Phillips. Most of her possessions—including letters to her from Winston Churchill and Eleanor Roosevelt—were sold at auction.

"There will never be another Ann Landers," Lederer told The New Yorker in the last years of her life. "When I go, the column goes with me."

Though her former syndicate offered newspapers a package of old Ann Landers columns plus a new column put out by her two assistants, called "Annie's Mailbox," and a syndicated version of Margo Howard's online column for Slate, called "Dear Prudence," insiders at the Tribune felt that the Ann Landers era was finished. The paper was still reeling from the deaths of its other signature columnists Mike Royko (in 1997) and Gene Siskel (in 1999), and some executives argued that the Tribune should no longer be in the advice-column business. But Jim Warren, the Tribune's deputy managing editor, and Ann Marie Lipinski, its editor, thought the end of the Ann Landers era presented an opportunity for the Tribune to create a star of its own and to do something even more ambitious: recalibrate the general advice column for the modern era. The advice column is read with prurient interest in many quarters today, but the fact is that it remains an especially powerful form of communication and consolation for countless readers around the country—that is, assuming the right person is behind it.

So how did Amy Dickinson become the right person? It's an unlikely story. After all, here was a woman whose first job out of college was as a lounge singer, and who one day was a housewife in London and the next was divorced and living with a two-year-old daughter in Washington, D.C. She and her daughter had moved to Washington in 1991, after her husband, Anthony Mason, a correspondent for CBS, abruptly retreated from their lives.

Dickinson knew few people in Washington, and had little in the way of career prospects. Her job, she said, was to raise her little girl, Emily Mason, to womanhood. Anything else she did was extra. "I took a writing class at Georgetown at night before I had any friends," Dickinson told me, "because I wanted to show Emily I did stuff outside the home. The class was stupid—it was mostly for elderly people. So I stopped going."

But once Emily began nursery school, Dickinson started to form a life for herself. She worked occasionally as a substitute teacher. She taught Sunday school. She freelanced for The Washington Post, Esquire, and Allure. (Before her marriage she was a producer at NBC.) She started doing commentaries for All Things Considered. She wrote a column for Time on family living, which ran from 1999 to 2001. In one memorable piece, in May of 2001, she lashed out at pundits who—pointing to newly released census data showing a rise in the number of single mothers raising children—claimed that the trend was yet another sign that the falcon could no longer hear the falconer, that things in America had finally fallen apart. Describing herself and her daughter, Dickinson wrote, "This family feels whole. It feels as if it works."

After Lederer's death Ann Marie Lipinski and Jim Warren received hundreds of unsolicited applications from all over the world—from suburban housewives, shrinks, already published columnists—saying that they were what the Tribune really needed, the next Eppie. One woman wrote demanding a contract, quoting her starting salary, and giving the address where her computer and fax machine should be sent. When her request wasn't met, she sent a virulent note demanding to know what the holdup was.

Warren, who had been a neighbor and confidant of Dickinson's in Washington when he was serving as the Tribune's Washington bureau chief (twice, by different people, they were set up on a blind date), scoured the country in search of a replacement for Lederer. When Dickinson said she would be interested in the job, Warren was intrigued. He had helped Dickinson land her job at Time, and he knew her to be smart and funny, a person with broad life experience, someone who knew the perils of being a working single mother. He also knew she was hungry; her column had been phased out at Time.

Warren sent her the sample questions he was sending to the other leading candidates. He had told candidates they had a week to get back to him; Dickinson's responses came that same day. Dickinson advised a man who had fallen in love with a second cousin, who was reluctant to admit their love to her family, that although a Cornell geneticist told her there would be no adverse repercussions if second or even first cousins conceived children, the fact that the woman wanted to keep the relationship a secret might very well mean she wasn't that attached to him. She gave a stern thrashing to some people who were fighting over the possessions of a terminally ill but not yet dead relative. And to a person who had spent a lot of money to attend the destination wedding of a rich couple and didn't want to have to buy a gift, Dickinson suggested an inexpensive but thoughtful offering, such as a scrapbook of pictures from the wedding.

Warren took the answers from six final candidates on vacation to upper Michigan. He convened several members of his wife's family as a focus group, and had them judge the sample columns blind. The judgment was unanimous: they all liked "No. 2"—Dickinson—the best. The Tribune subsequently held other, more formal focus groups in the Chicago suburbs, but by the time Dickinson arrived in the city for her job interview, on October 17, 2002, she was already a clear front-runner. After several months of deliberation at the Tribune, she was offered the job, and her column debuted on July 20, 2003. The intent was clear: by putting her in Ann Landers's old space, the Tribune was using the Landers franchise to launch Dickinson to readers.

Her arrival was not without controversy. After an interview on CNN in which Dickinson promised readers a "funnier" and "more entertaining" read, Margo Howard (whose syndicated column the Tribune canceled when "Ask Amy" debuted) told Newsday, "Nobody compares her favorably to my mother except herself."

"I think what stuck in her craw was the use of the Ann Landers name," Dickinson told me. "The Tribune used the phrase 'the new Ann Landers' to market this column. And she didn't like that at all, and I don't blame her. Strictly speaking, they were correct. The paper was replacing the Ann Landers column. That doesn't mean that I am any replacement for Ann Landers. But they were making this association for the readers. And you know what? It worked. It got a lot of attention. But Margo, they also canceled her column, and she hates that, and one day I expect that to happen to me, and I'll hate that."

Dickinson never knows what she'll find when she walks into her small office on the fifth floor of the Tribune building each morning. (Unlike Lederer, she is without assistants or a wing to herself.) Hanging on a bulletin board are columns sent back to her by readers. One has "HORSESHIT" stamped in red across it. Another has "B.S.!" scrawled in black pen across her words. Alongside these columns is a postcard that says,

Hey Amy—how come you can be an "advice columnist" and dispense all kinds of wise stuff to people about their love life ... and we understand you are listed as a single parent!!! ... How come you don't have a husband? How come you can't hold on to a man? Why don't you take some of your own "advice" and keep a stable home life for your kids? How come you don't address this in your column?

"I think putting up the 'Horseshit' and 'B.S.' stuff has been good for me," Dickinson says, "because it's a reminder there's a guy out there with a 'Horseshit' stamp, and he's prepared to use it. And I don't want to be afraid of the 'Horseshit' stamp, because then I'm a lost man. All I've got is my own point of view. It's just a reminder that it's going to be okay; it's something I have to go through."

It's fair to say that Dickinson has a job quite unlike any other. The task of most beat reporters is to work sources, sometimes by promising them anonymity, to get them to reveal information they normally wouldn't share. Over time that stress can wear you down, or drive you to drink. Dickinson's stress is different: her stories come to her in an overwhelming flood. She opens all her own mail, reads all her own letters.

The flood of input is not limited to the mail. One day, as we sat talking in her office, Dickinson answered the phone to discover an angry reader named Florence on the other end of the line. Florence was upset that Dickinson had used the words "safe sex" in a recent column.

"So you don't think there's any such thing as safe sex—is that what you're saying?" Dickinson said. "Okay. Okay. I can't change it, because it's already been written, but I really appreciate your point of view. Do I believe in it? Well, when I say 'safe sex,' it's just kind of terminology. The only safe sex is no sex—is that what you mean? I understand. Okay, thanks for calling."

Dickinson's column schedule works on a model that is the reverse of the New York Times crossword puzzle's: she begins with hard issues on Monday and gets lighter as the week goes on. Sundays are reserved for spiritual matters. Unlike Lederer, Dickinson rarely answers letters that won't be published, which explains why she gets e-mails like this one:

I sent you a letter and have not heard a response from you as of yet. It was regarding a relationship I have been having with a married man for seven years now. I wanted your advice on that. AND I WOULD APPRECIATE YOUR ANSWER AS SOON AS POSSIBLE.

She does not change the wording of a question, and she does not try to respond with pointed, one-paragraph responses, as Lederer did. Indeed, her answer is sometimes twice as long as the letter.

Love connection but with a catch
Dear Amy: I am getting tired of hearing about the women who can't find nice men. You tell them that looking in a bar is the wrong place.
     I have an alternative place to go to find a guy: the local comic-book shop. I don't mean the single spinner rack at the local chain bookstore but a real comics shop. I know it sounds strange, but comics are not just for kids. They're great storytelling devices.
     Men who go to comic-book shops have good values, are of all sizes and ethnicities, and the time they spend in the shop and reading is time they are not cheating on someone or getting sloppy drunk.
     Go on a Wednesday, because that's when the new issues get delivered.
     —Comic Genius

Dear Genius: First, let me clear this up—I don't tell people not to go to bars to meet one another. I tell people that there is a good chance that the people you meet in bars will be the sort of people who like to go to bars. Does that make sense?
     I love your suggestion, so I field tested it at a comic-book store in downtown Chicago—on a Wednesday.
     You're right! There were lots of guys there!
     However, here's the thing about comic-book stores—the guys who go there really like comic books. I spoke with a female employee who said that the ratio of men to women is very favorable (to women), at about 20-1, and that they all have something in common: They really like comic books.
     What I like about your idea is that it is a great reminder that it is good for all of us to leave our comfort zone. Trying new things makes people more interesting. Interesting people are more attractive.
     The problem with your idea is that comic-book stores are full of people who really like comic books. Which brings us back to my bar theory: When you choose to meet people at a place that has a very specific focus, it helps if you share that focus.
     Comic-book collecting is a hobby, which—as absorbing as it is—isn't everyone's cup of tea, though I did pick up a couple of "storytelling devices" myself.

Dear Amy: I am a recovering alcoholic. My side of the family are all alcoholics. On my husband's side, they are not.
     Some time ago I had a relapse, and nothing has been the same since. My husband says I should have nothing to do with my mother (the source of the problem), and there is nothing I can do to assure him there is nothing going on with me as far as alcohol.
     My mother is 80-plus years old, and I am worried about her health. I have a sister who lives close by, but she can do only so much.
     My husband gave me an ultimatum today, saying not to go to my mom's again. He totally does not trust me. What do I do, and where do I turn?
     —Upset but Sober

Dear Upset: Ultimatums often come at the end of a long road of broken trust. Spouses don't generally jump to ultimatums without first suffering some betrayal. I'm going to assume that your drinking has taken its toll on your husband.
     You may be able to negotiate a settlement of sorts with the help of a third party. If you are members of a faith community, your clergy could sit down with the two of you and hear you out. If you can find a therapist with some experience in dealing with addiction and recovery, counseling could help both of you breach this impasse.
     I also must suggest AA and Al-Anon; you both need the continuing support of a community of people who understand your lives and experiences—from the inside.

A day spent reading Dickinson's letters is both a reminder of the universality of human experience and a barometer of cultural trends. There are timeless letters from the brokenhearted, who cannot sleep, who cannot trust; from a woman with a sexless marriage whose husband seems always to be hanging out with a certain female co-worker; from the twenty-nine-year-old girlfriend of a divorced man who cannot stand the affection his ex-wife shows him. But there are also angry letters from grandmothers upset at the belly-shirts their granddaughters wear. There are e-mails from affluent and middle-income people tired of being hit up for every benefit or walk for diabetes or breast cancer. And there are truculent responses from animal owners, to whom Dickinson has tried to explain that their pets are not human beings.

And, of course, there are the crush letters. Following an appearance on CBS Sunday Morning, she received two e-mails. One was from a man in Florida, who told her she looked great and that they should meet for coffee and do some "mutual pleasuring." Another came from a lesbian who wanted to get together and have lunch at the Four Seasons. It was signed, "Very Gaily Yours."

"I think that I have this 'hapless' thing going for me," she told me. "In my present column I'm very open about being this hapless, middle-aged, single woman. When people write about dating, I kind of laugh along with them, because I've had my share of blind dates. So I think I come off as this quirky single woman. I don't, quite frankly, think of myself as a single mom, but it's an important part of my public persona." Throwing her head back, Dickinson joked, "So now it's like I can't ever be hooked up with a man, because it works for me professionally, being single."

One afternoon, as Dickinson and I watched Dr. Phil and ploughed through a box full of clipped, mutilated "Ask Amy" and "Dear Abby" columns, sent by a clearly troubled reader, there was a knock on the door. A Tribune writer—who wishes to remain nameless—had come up with the solution for a problem of her own, but wanted to run it by Dickinson, whom she referred to as "Ask." The previous year, through Match.com, she had met a man who spent ten years on Wall Street and then returned home to Nebraska, where he owned a 30,000-acre ranch. He had flown to Chicago for a date. That had gone well, so she had traveled to Nebraska for three or four days. That hadn't gone as well.

"It was too much time," the nameless writer said. "Too much of him. You just can't go from not knowing somebody at all to being around each other constantly."

But in recent months, she said, she hadn't been able to stop thinking about this guy, and in recent weeks the two had gotten back in touch. She wanted to invite him to an event at the opera, but she didn't want him to stay at her place. It wasn't that she didn't want to sleep with him—she didn't know yet whether or not she did. But she had a small apartment, and the weekend could be choked with tension. Would he be insulted, she asked "Ask," if she offered to put him up at the W Hotel?

"Wouldn't a guy be insulted if a girl did that?" the woman asked, turning to me.

"I'd be a little disappointed," I said.

At this point Dickinson, having turned down the volume on Dr. Phil, began to establish how things should be. Yes, the writer should invite the man to town, but she should say, "Please let me put you up at the W. It's the coolest hotel in town. It's got the greatest, best bar, my place is super-tiny, and I'm really excited to see you." Dickinson said, "I just think that's really proper but it's also polite. It's a really lovely gesture to make."

"I am so excited for you," she continued. "And your hair looks great. I'm really, really excited for you. Somebody might be getting some. God willing."

"God willing," the writer said.

Perhaps Dickinson's greatest natural asset is the ability to draw people's problems out of them, even in real life—not feeding on these people as if she were drawing strength from their misery but, rather, responding to them with empathy and warmth and understanding.

Naturally, over the days I spent with Dickinson I found myself starting to tell her things—especially about the previous twelve months, a year I've officially categorized as the worst of my life. I told her how I'd left a good job and the graces of an editor I hold in my heart second only to my father in order to work for more money at a multinational corporation from which, each day, I would come home feeling battered and intellectually unchallenged and devoid of hope. Over dinner (and two glasses of bourbon) one night I told her about how I'd fallen in love, real love, for the first time in my adult life, with the woman I thought would be the mother of my children—only to have my heart shattered. I told her about a friendship that had effectively ended alongside the breakup, and about … well, you know. Dickinson listened and related her own work and love experiences, making me feel better. Which I suppose is what a good advice columnist does: she shows you that you are not alone in the world, shows you that someone understands, lets you know that everyone goes batshit sometimes, and that recovering from it can lead you to expectations and views that translate to a new life, a better life.

In Dickinson's home town for Halloween weekend, I began to understand where this ability comes from. Freeville, New York, where her ancestors settled in the years after the Revolutionary War, is the kind of place Garrison Keillor deadpans about, but whose complexities Thornton Wilder truly understood. Here she was raised, the youngest of four, on the dairy farm at the edge of the village that her father, Charles "Buck" Dickinson, tried to manage until it simply overwhelmed him. He left it and his family when Amy was twelve. Making the best of it, Dickinson's mother, Jane, sold the livestock and equipment at auction and at forty-eight became a typist at Cornell. Two deans encouraged her to enroll in the school full time and earn an undergraduate degree. An MFA followed, as did a real career—a fifteen-year stint teaching at Ithaca College.

"It informs me," Dickinson says of her hard early-life experience. "I feel like I know what loss is, and also when I hear from people with family rifts, these issues and problems that go back for decades, I get it. So I just don't say 'Get a life.' When people say 'Just get it together,' if any of us could, we would. Wouldn't that be my first choice? But I feel like I know what it means to get a life—it's a combination of bootstraps and real emotional resilience and temperament."

Given what has happened to her in life, one can understand how Dickinson, a popular, stay-out-of-trouble, participate-in-everything girl in high school, might have turned into Miss Lonelyhearts, the forlorn, dispirited, and ultimately hateful advice-columnist character in the bleak novella by Nathanael West. After meeting Anthony Mason her junior year at Georgetown, Dickinson spent most of her twenties in his shadow as he grew prominent in TV news. Dickinson followed him, first to New York and then to London, settling into life as a housewife and a mother. Though based in London, Mason was rarely around his wife and infant daughter. By his own estimate, he told me recently, he spent 260 days away from home one year.

In 1990 Mason ended the marriage. The divorce is something that Dickinson is "still dealing with," according to her closest friend, Kirk Read, a professor at Bates College, in Maine. "I think she's still coming to grips with what that all meant," he says. If anything, Dickinson told me, her being divorced helps the column. "I can still sit on the bus and sob over my divorce," she said. "You know, it's easier for me to write about divorce than it is to write about marriage. When I write about marriage, it's an abstract concept to me. It truly is at this point. I'm much more comfortable and much more intimate with divorce. Some of the marriage questions really take much more work and thought for me, because I have to imagine what these long, long marriages are like."

"Somebody who knows me pretty well said, 'Wow, you really take this seriously,' and I was shocked," Dickinson said of one person's response to how she approaches her work. "I think I have this reputation for having this caustic sense of humor. If I didn't think that people could change and feel better, then I wouldn't do it. Every single morning I get up and go running along Lake Michigan and tell myself I'm going to be better. I have to think that. We have this desire to improve ourselves. And I feel like I'm a part of that."

One afternoon, a few days before Halloween, Dickinson and I visited an after-school program, set amid the ill-begotten high-rises of the Cabrini-Green public-housing project. It looked like any other after-school program for the disadvantaged: there were games and a few computers, a few eager volunteers. After telling the kids what she does for a living, Dickinson began to field questions from them. She took a few easy ones, and then one girl raised her hand and said, "Some of the kids in my class don't like me, so they threaten me—they threaten to hit me and stuff. What do I do?"

"Part of it is being strong," Dickinson replied. "Part of it is not being scared or acting scared. I know it's just hard to do, but if you can just keep your back straight and show somebody that it doesn't bother you, they will leave you alone. It doesn't mean you need to threaten them or give them a hard time. It just means you need to straighten up and walk away."

One person who requires Dickinson to keep her back straight is Margo Howard, who lives with her fourth husband, a heart surgeon named Ron Weintraub, in Cambridge, Massachusetts. Having recently broken her ribs falling down the stairs, Howard told me on the dark November day when I came calling, "If you're ever going to be in the emergency room, make sure your husband is the chief of surgery."

Howard is a polished woman. After making some coffee she said, "Come, my boy," and ushered me into a living room where, among other ornate objects, sits a bench once owned by Somerset Maugham.

Howard was straightforward about the controversy surrounding the aftermath of her mother's death: Lederer didn't want a large funeral, and there was no reason to include Jeanne Phillips—whom, Howard said, her mother rarely saw—at whatever service was held. As for the sale of Lederer's possessions, Howard said that her mother hadn't been concerned about the fate of her material things, and had told her in writing to do whatever she wanted with them after her death. Some had gone to the Chicago Historical Society, and Howard planned to donate other items to the Radcliffe library.

"I was sixty-two when she died," Howard said. "I've had four husbands. I have a nice bank account. I have furniture. What did they want me to do with things from a fifteen-room apartment? What is wrong with them? I just took what I loved. I don't know what's up with these people who say, 'How could she?' It made no sense. It was a way to come at me. I became the target. Do not ask me why. There I was with a sign on my forehead: 'Let's say something nasty about Margo.'"

Howard, who answers four letters a week in her online Slate column, is frank about her feelings toward Dickinson, whom she describes as "no great shakes." "She's not the new Ann Landers," Howard told me. "She's the new advice columnist. That's what the Tribune should have done, said 'Here's our new advice columnist.' All she can do is look tarnished by reflection. I resent this attempt to slide in on my mother's reputation and her name."

Howard and I spoke about how many people her mother had touched during her tenure, and about how much she loved her. She told me that with her mother's passing, the great power of the general-interest column had officially come to an end. As I got up to leave, she asked me, "Honey, do you have a real life?"

"A real life?" I asked.

"A partner," she said. "Somebody you like."

"I had a girlfriend," I said. "I don't have her anymore."

"A gone girlfriend," Howard said, and then asked, "Are your folks in this country? Do they care if you settle down with an Indian girl?"

"They used to," I said. "They don't care anymore."

"Like the old Jews," Howard said. "They gave it up. This is funny—imagine what my mother did for a living, and having a kid with three divorces. She was terrific about that. Actually, she said it would be good if I only dated Jewish boys. Marriage is tough enough without introducing religious differences. I got two dispensations: one was for an Indian kid who was at MIT and whose father was on the supreme court of India. The other one was an exchange student at Harvard. He was the Aga Khan. I didn't want to cross Mother, but neither did I want to pass that up. So I sidestepped it with the old lady, and told her, 'Listen, there's an exchange student at Harvard named Khan—what do you think?' That's often a Jewish name, so she said okay. And I don't know if she was right or not: the current, wonderful, last husband happens to be Jewish—but my other good marriage was to a Christian."

"Do you find yourself drawn to Caucasian girls?" she asked.

"I guess," I said. "I date them."

"You go for it," she said. "I'll protect you, because I'm an advice lady."

But I already had an advice lady. And on a cold, rainy day the following week I found myself in my office in midtown Manhattan, unable to work. I'd grown used to Dickinson, and had come to rely on both her counsel and her comforting physical presence. Hell, I'll say it: I missed her, and I told her so in an e-mail.

Dear Amy: I'm a reporter working on a piece about an advice columnist and I've become addicted to the advice/support she's giving me. Is this a common occurrence? What should I do?
     Best,
     Advice Junkie

A few minutes later a response came.

Dear Junkie: Ideally, an advice columnist is just an efficient delivery system for common sense. I can see how a person would become reliant on that. But the whole idea here is for you to develop your own boundaries, your own radar, and your own voice. Remember—the Great and Powerful Oz was really just a guy behind a curtain.
     The next time you find yourself jonesing for another advice fix, I want you to look in the mirror and ask yourself, "What would Amy tell me to do?"
     Then I want you to go ahead and do it.