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Baffled In Boston


--Excerpted from Gary’s articles, including:
“The Man Who Would Be Ann” (published in Writer’s Digest magazine)

I have this theory that I should always have ten writing projects started because nine of them are going to be disasters. So last March when I applied to replace Ann Landers at the Chicago Sun-Times, it wasn’t because I was ready to flush the rest of my life down the toilet. Applying for the advice columnist job, to use a more pleasant analogy, was just planting one more seed in my garden. . . .

When I saw the newspaper’s ad, in which the Sun-Times confessed that Ann was abandoning them and they wanted to replace her with someone who had “Guts, Guidance, and Good Advice,” I didn’t trouble myself with nitpicking questions like, “Do you really want this job, Gary?” . . .

Of course, I was not the only applicant. Twelve thousand hair stylists, taxi drivers, manicurists, bakers, candlestick makers … along with half the sex counselors and writers in America, joined the party. Though I was in the middle of writing two books with imminent deadlines, and preparing for a workshop, I stole the time to write a letter extolling my virtues to the Sun-Times. . . .

Mostly I promoted myself as a communicator. . . . I had written 20 books, 14 of which were good enough to be published. And the six dreadfully written unpublished ones piled in my closet only proved that I was familiar with rejection, failure, frustration and anguish, the very tragedies advice-seekers would write to me about.

I had also written a thousand articles, many of which took the form of advice to writers right here in Writer’s Digest. I reasoned that if I could inspire writers to persevere in the face of grim publishing realities, helping people deal with alcoholism, family feuds and broken hearts would be as easy as typing.

A week after I mailed my resume, I got a letter from the Sun-Times. I thought it would be some variation on a rejection slip. Instead, I learned that I had made the first cut. A hundred and seven other people had also made the first cut, so it seemed a little early to invite the gang over for a celebration party.

The Sun-Times also sent along four sample letters addressed to “Dear So-and-So.” I was to answer them before sundown the next day, a deadline which was particularly disheartening considering that I was near death with the flu.

One letter concerned AIDS and it left no room for humor. I saw it as a test. Would I know enough to scrap the jokes and also gather such sensitive information from reliable sources? I called the National Health Center and wrote a straightforward letter.

The other letters seemed to invite levity. One man said he had a gut feeling that his wife was having an affair with his brother on those nights when she was allegedly at “business-related dinners.” He ended by saying he didn’t want to be the last to know.

I wrote back, “The simple solution would be to invite your brother over for a game of pinochle every time your wife has one of those business-related dinners. If he continually declines with curious excuses like, “Gee, I’d love to, but tonight I have to wash my parakeet,” then perhaps there is some basis for your fears.”

My letters were good enough to get me into the final 22, and when I answered another set of four letters, I got a call from the Sun-Times.

“Welcome to the final seven,” a woman said.

Now it was serious. Channel Seven came on Thursday, Channel Five on Friday . . . I spent entire days with the press. . . . The “Oprah Winfrey” show flew me to Chicago to do a program with the other finalists. . . . There were six of us, three women, three men. Number seven, “the mystery woman,” had declined publicity. Poor her, we thought, she doesn’t have a chance. After all, publicity was what this was all about. We became close quickly, the six of us. And why not? We were peering out at the world from the same goldfish bowl.

A week later I was in Chicago again. This time for “The Interview.” Four editors surrounded me. . . . What do you think about abortion, they asked. What about divorce? What about this . . . about that? You wouldn’t cut in line at an airport and embarrass us, the way Ann once did, would you? And by the way, you have to move to Chicago for this job, and we want you to know we’re thinking of picking a man and a woman.

I told the Sun-Times I would move or share the job, but not both. If they decided on a man and a woman they could count me out. I didn’t want to relocate just to become half of the new Ann Landers.

We’ll let you know on May 18, they said.

When I got home the phone was ringing and it never really stopped. Have you heard anything, Gary? It wasn’t just reporters and friends. It was friends of friends. It was men who had sat beside me on a bus one time, women who had the same optometrist as me. I enjoyed the attention but I was getting bored with hearing me report the same lack of news over and over.

The 18th of May came. The 18th went. And as that deadline receded farther and farther into the past, without explanation, I and the others took a turn for the worse. . . .A telephone network of Ann Landers finalists began communicating across the country. . . . We had a dozen theories a day. . . . “Any day now” turned into “any week now.”

When the Sun-Times finally called, it was to tell me they had picked two people, neither of whom was me. The paper had selected the mystery woman, Diane Crowley, also from Massachusetts, and daughter of the original Ann Landers. Her partner was to be Jeffry Zaslow, a writer for the Wall Street Journal.

Though the contest was over, the adventure continued. I and two other finalists—Linda Stasi and Linda Moore—created “Almost Ann,” a parody of advice columns, which was picked up by a major syndicate. . . . National Public Radio asked me to give occasional on-air advice for “All Things Considered”. . . and a local radio station asked me to be its funny advice columnist.

And best of all, I’ve started writing a novel called Dear So-and-So [later published as Baffled In Boston]. It’s a comedy about a guy who enters a contest to replace a famous advice columnist. It’s one of the books I really want to write.

So that’s four projects I’ve started as a result of not being the next Ann Landers. If I can get six more, perhaps one of them will work out for the best.