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Advice for Advice Columnists

This month the nation mourned the death of Pauline Friedman Phillips, the author of Dear Abby. For 40 years, Phillips dispensed thoughtful, compassionate, and occasionally wry advice in more than 1,400 newspapers. She received up to 10,000 letters per week.

I’ve always been in awe of advice columnists. They’re astoundingly astute, a rare species of human able to inhale chaos and exhale clarity. Nothing jiggles on them. Nothing flaps. They’re so smart. So sure. So shiny.

I once interviewed Washington Post advice columnist Carolyn Hax, who is perhaps the most shockingly sensible person ever to peck at a keyboard. Star-struck, I giggled nervously and guffawed embarrassingly throughout our chat. She was like the Dalai Lama, and I hoped she would bless me with a sprinkling of her uncanny-sanity dust.

But she didn’t. So let’s call it “her fault” that when I recently began writing my own advice column — Tough Love on — I found the task thrilling and stimulating and fun … but chest-squeezingly, brain-painingly, teeth-grindingly hard. So far, I’ve been hit up for help by a woman with herpes, a man whose wife dresses him funny, and a mom who caught her teen smoking pot.

The writing itself is a challenge: How do you craft a response that both entertains readers and satisfies the question-asker — and how do you decide which is more important? The responsibility is exacting, too: What if your advice is lousy and readers take it to heart, then write back saying you’ve made their already awful life worse?

Surely Abby and Hax never struggled with such uncertainty … right?

Cheryl Strayed, who writes the beloved Dear Sugar advice column on, came to town recently to speak at UCSB Arts & Lectures. I grabbed a few minutes with her to ask how she does what she does — and to find out if I’m the only advice columnist ever to need, er, advice on how to do the job.

It was wonderful. We commiserated over the fact that snarky responses are terribly tempting but totally inappropriate, and that we feel obliged to imagine and address every possible outcome of each writer’s situation.

Strayed, who also wrote the best-selling memoir Wild, took over Dear Sugar from a friend when it had no following and paid nothing.

“I thought it would be interesting — real people telling me their secrets,” she said. But as soon as she began reading their gripping questions, “I realized it wasn’t going to be this funny little thing. I was going to put everything into that column.”

And she did. Her responses are long, compassionate literary essays full of her own intimate life stories. A father grieving the death of his only son once wrote this to her: “Your column has helped me go on … Your words feel sacred to me. They hold me up.” (Did I mention how one reader responded to my advice? “Dear Abby this is not.”)

Strayed told me that after almost three years of writing Dear Sugar, it still hurts her feelings when strangers say they don’t like her. She’s had to accept that she can’t respond to every desperate query, and to decide which ones she’s capable of answering (drug addiction, cross-dressing, marital affairs) and which she isn’t (should I give my baby up for adoption?).

Finally, I asked her this: As a proven expert on getting unstuck, does she ever get … stuck?

Of course, she replied easily. “I’m down in the muck with everyone else, trying to be the great mother and failing at that sometimes, trying to make a marriage last.”

I hope the next time she’s unsure about such things, she’ll write in for my advice. Honestly? I think I could help.

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