Ask Anything, Tell All

Image Gallery Linda Zacks / www.lindazacks.com

Five months after the death of Esther “Eppie” Lederer in 2002, the bulk of her estate—a sprawling Chicago apartment’s worth of furniture, photographs, papers, and memorabilia—went up for public auction with some fanfare.

Lederer, who was better known by the pen name Ann Landers, had for almost 50 years written America’s foremost newspaper advice column. With an estimated 90 million readers, the self-described “nice Jewish girl from Sioux City, Iowa,” was often counted among the most influential women in the United States. What was most remarkable about that influence was its breadth: She advised teenagers about pimples and presidents about missile defense—and the presidents often wrote her back.

Before her death, Lederer made clear that the Ann Landers pseudonym, which she had inherited in 1955, would die with her. But that did not prevent would-be successors from seeking to assume her mantle in more symbolic ways. On the auction block that November were Lederer’s writing desk and typewriter, on which she had composed responses to correspondents like “Desperate in Denver.” When the bidding was over, an advice columnist named Dan Savage happily walked away with them. Today, the desk sits in Savage’s office in Seattle, where he serves as editorial director of the city’s alternative weekly The Stranger and writes his own hugely successful weekly sex advice column, Savage Love. His correspondents have included a woman signing off as “Fucking Asshole Idiot Losers” (FAIL), who faced a very modern problem. “My husband and I have a ‘don’t ask, don’t tell’ policy when we’re apart,” she began.

“A few months ago, I hooked up with a guy on a business trip who said he and his wife have the same arrangement. He was lying. His wife found out and started harassing me on Facebook. I truly feel horrible. How can I know if someone is really in an open relationship when they say they are?”

Savage pointed out that “the only way to verify that someone is in an open relationship is to speak to that person’s partner—and as that would constitute ‘telling,’ FAIL, it would be a violation of a ‘don’t ask, don’t tell’ policy.

“But even a couple with a ‘please ask, do tell’ policy probably has a rule against 2:00 a.m. calls from drunken hotel-bar pickups. So you’ll have to trust your gut, FAIL, which failed you here. Just remember this on your next business trip: The further a married person is from home and the drunker that married person is, the likelier it is that that married person is lying to you.”

Suffice it to say, Savage is not the most obvious heir to Landers’ ultra-mainstream legacy. His columns answer a Chaucerian panorama of correspondents: gay Mormons, incestuous siblings, weight-gain fetishists, men yearning to be cuckolded, and otherwise ordinary Americans grappling with an extraordinary range of problems and proclivities. By the standards of a family newspaper, his advice is not only explicit but broad-minded to the point of being radical, encouraging people to embrace or at least tolerate previously unmentionable sexual inclinations in their partners, praising open relationships, and celebrating behaviors that might cause even the most intrepid reader to balk.