Margo Howard’s first marriage, at age 22, to John Coleman—a financier, and her “starter husband”—lasted seven years and produced three children. Her second, to Jules Furth, a funeral director, ended three years in. Cause of death: “boredom.” (Howard says she takes comfort from the saying “Every woman should have a forgettable second husband.”) Her third, to “Mr. Right No. 3,” the actor Ken Howard, lasted longer, but ended similarly. “I don’t really know when trouble found us,” she writes in her new memoir, Eat, Drink & Remarry. “But my best recollection is that it was on one side or the other of our being together for ten years.” After the divorce, Howard kept Ken’s last name but ditched Los Angeles for Cambridge, Massachusetts.

One April evening, 22 years later, I am having dinner with Howard in a corner booth of a swank restaurant in the Cambridge hotel where she has owned an apartment since 1987. Her fourth husband, Ron Weintraub, a cardiothoracic surgeon, has forgone dinner to see the Boston Symphony Orchestra perform Mahler’s Symphony No. 5. Howard and Weintraub have recently returned from their annual winter migration to Florida, and the hotel’s entire staff seems pleased to see her. “Ron and I often joke about this being our dining room and that being our coffee shop,” Howard says, gesturing across the way to the hotel’s other restaurant. “I guess that makes me an elderly Eloise,” she adds, referring to the children’s-book character who lives at the Plaza Hotel and enjoys a life marked by carefree misadventure.

Howard, who is 74, has flame-red hair, enormous round glasses, and paper-white skin. (When he met her, in 1997, Weintraub thought she looked like a Kabuki dancer.) Her speech is sprinkled liberally with honeys, as in: “Oh, honey, we are so not sporty” and “Well, honey, I was ancient then; I was 57.” She does not shy away from confessing her mistakes, whether marital or otherwise—in a sense, her new book is a chronicle of them. More generally, she has a healthy supply of what she would call chutzpah. See, for example, her decision, back in 1998, to hang her shingle as an advice columnist, despite having failed three times at marriage, and despite her minimal acquaintance with the average person’s practical and financial difficulties. (Howard has employed domestic help, in the form of housekeepers, butlers, drivers, baby nurses, and nannies, for all of her adult life.) Over a Kir (her drink of choice), she tells the story of how, at age 8, her son looked in his baby book and deduced that the family had been celebrating his birthday on the wrong day. “I don’t want you to feel bad,” he told her, “but this isn’t my birthday.” “I’m not going to win Mother of the Year,” she says, pausing to greet the chef, who has just stopped by to chat.

Based on her personal circumstances––the cosseted lifestyle, the failed marriages—Howard might seem an unlikely figure to be advising others. And yet her foray into advice writing was not as unlikely as it appears. She descends from advice royalty: Her mother, Esther “Eppie” Lederer, who died in 2002, was better known to the public as Ann Landers. Her late aunt, Pauline “Popo” Phillips, started the Dear Abby column (which today is written by Howard’s cousin Jeanne Phillips). Howard for many years resisted getting into the family trade, despite her mother’s insistence that she had “the advice gene.”

For one thing, she regarded advice as “the ole lady’s deal.” For another, she saw herself as a “straight newspaperwoman,” having been given her own column at the Chicago Tribune at age 29, in which she wrote about everything from the Playboy Club to the feminist movement. From there, she went on to write commentary and celebrity profiles for publications ranging from The Nation to People. All the while, she was busy marrying, and unmarrying, prompting the longtime Chicago Sun-Times editor Jim Hoge to quip that “writing is what Margo does between husbands.”

Finally, in 1998, Howard’s friend Michael Kinsley, who was then the editor of Slate, convinced her to take over the site’s Dear Prudence column. From the beginning, Howard knew that she wanted to approach advice a bit differently than her mother had. Writing as Ann Landers, Howard’s mother had famously fetishized experts. “I didn’t want to do that,” Howard told me. “I was thrice divorced, analyzed, bordering on elderly, and I thought, My answers are going to come from my experiences.” To that end, she did not hesitate to recommend divorce or estrangement, from family members and friends alike.

Advice columnists are not, as a group, known for living perfect lives. To the contrary, this is the rare field in which personal problems appear to give an expert a leg up. Cary Tennis, who was until recently the advice columnist at Salon, is a recovering alcoholic, a fact that seems to have profoundly informed his work, leading him to counsel advice seekers to be more accepting and forgiving. Cheryl Strayed, of Dear Sugar fame, has wrestled with infidelity and drug addiction, facts she uses to reassure readers crippled by perfectionism. Dan Savage, of the Savage Love column, draws on his own complicated sexual and romantic history, to sometimes crude but great effect. Carolyn Hax, whose Washington Post column is syndicated in more than 200 newspapers, got divorced and then quickly became pregnant with twins before marrying her second husband, a turn of events that she addressed forthrightly and that appears to have inflected her work with a striking humanity. Howard’s own mother and aunt famously feuded for years. All in all, Howard says, advice columns are “the prime example of ‘Do as I say, not as I do.’ ”

Howard got out of the advice business last year. After eight years writing for Slate as Dear Prudence and another seven writing a syndicated column under her own name, the time had come. “I had said everything that I needed to say,” she tells me. Besides, the troubles of post-recession America—“People have lost their homes, they have lost their jobs”—struck her as beyond any advice column’s capacity to mend.

There’s no doubt that the genre has changed dramatically in recent years. Landers doled out advice in an analog world; Howard helped retool her mother’s conventions for the Internet. In turn, over the past 20 years, freed from the space and other constraints of the women’s pages, advice columns have proliferated, many with exceedingly specific angles on the world. “There developed a whole bunch of niche advice columns,” Howard says. “For teenagers, for old people—I can’t even think of them all now. For pets!” The format has never been more vibrant or—judging from the Internet traffic generated by columns like Dear Prudence—more popular.

But even as the genre has transitioned away from expert-driven advice and toward the more confessional mode of Strayed and others, the Lederer family’s influence continues. Take Dan Savage, who grew up reading Landers and says that her columns helped him get through his years as a closeted gay teen. Savage sees himself as following in Landers’s footsteps in some regards. He has cultivated a friendship with Howard, asking her blessing to buy Landers’s desk after her death.

I find myself wondering what Howard must make of Savage’s raunchy, wickedly funny brand of advice. “Dan has a saying he abbreviates to DTMFA—Dump the Motherfucker Already,” I volunteer, thinking the idea might resonate with Howard. “It has a Jewish tang to it—already,” she replies appreciatively. “People would write in and say, ‘You and Dan Savage are my favorites.’ Well, I thought, that’s pretty strange. Had my mother read what he was writing, she would have needed smelling salts.” She pauses. “I said to Dan, in an e-mail, ‘This makes no sense. How could people like you and like me?’ He said, ‘Because we’re both straight—pardon the expression! You know: we’re honest.’ ”