Author Cheryl Strayed: on Dear Sugar, Keeping the Faith, and Palling around with Oprah

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Joni Kabana
Cheryl Strayed
By Byard Duncan

Last Valentine's Day, author Cheryl Strayed stood onstage at the Verdi Club in the Mission and told hundreds of strangers the biggest secret she's ever kept.

The revelation? For two years, Strayed has been the voice behind "Dear Sugar," an anonymous advice column that appears on the San Francisco-based literary web site The Rumpus. In her time as Sugar, Strayed produced almost 100 columns and amassed millions of page views. Her guidance -- part floral prose, part unvarnished emotionality -- routinely went viral, and created legions of quietly bawling cubicle jockeys across the nation (this reporter being no exception).

On July 10, Vintage released Tiny Beautiful Things, a collection of Sugar's best columns, along with a handful that were never published online. And on July 27, Strayed will return to the Verdi Club for a Rumpus-sponsored release party for the book.

SF Weekly spoke via telephone with Strayed, who has been touring in support of her recently-released memoir, Wild, since March. (Read our review of Wild here).

You revealed yourself as Sugar here in San Francisco five months ago. How has your experience writing the column changed since then?

I've written fewer columns than I thought I would. I knew I was going to have to take time off to go on my book tour, and my writer friends kept saying, "You're totally not going to be able to write the column while you're on your tour." They were right, and little did anybody know what would happen with Wild and how much more of a tour I would be doing than first anticipated.

What's fascinating is [writing the column] is exactly how I suspected it would be. I knew that I would continue writing it the way that I always do. The same sort of feeling I have when writing the column I've had writing the columns since then.

I still respect the parameters of "Sugar Land," if you will. I say "the city I live in." I don't say "Portland, Oregon." I don't say "Brian" (Lindstrom, Strayed's husband). I say "Mr. Sugar." Long before I revealed my identity, I was writing from Cheryl -- Cheryl as Sugar. And so I haven't experienced any shift whatsoever in my experience of how it feels to be the person writing the column. The columns that I have published since, people in the comments section have said the same thing. They're like, "Oh I was so afraid it would be different, but it's not different."

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There are a lot of common themes -- sexuality, loss, dependency, abuse -- running through both Tiny Beautiful Things and Wild. How have your two writing identities changed or merged over the past six months?

I've always felt like I was Cheryl writing. The Sugar persona was just that -- a little veneer. I was maybe slightly sassier, and also I could be, because of the direct address. Wild is a traditional memoir. What I mean by that is the voice is not speaking explicitly to the reader, even though of course I know the reader is there, and I am speaking to the reader. But I'm using that narrative voice, where there's this wall between the writer and the reader.

With Sugar, there isn't a wall. I'm talking directly to the reader, and I know that a bunch of people are listening in as I give that person advice. I think the Sugar persona comes more from differences in the form, not so much the differences in my style or voice or anything like that.

And I did write these two books -- both Wild and Tiny Beautiful Things -- sort of right on top of each other. I had finished the first solid, full, polished draft of Wild and sent it off to my editor, and the next week is when (Boston-based author and former Sugar) Steve Almond emailed me and said, "Do you want to write this Sugar column?"

It was while I was finishing up Wild and doing the last revisions that I was writing Tiny Beautiful Things, not knowing I was writing Tiny Beautiful Things -- just thinking I was writing this column. So inevitably, one blended into the other. There were even some times when I'd be revising Wild and realized that there was a certain scene that I didn't need in the book that I took out of the book and ended up in a Sugar column. The anecdote about my ex-husband and I, on Christmas day, cracking open our ceiling and finding those two kittens in this building in New York City - that was originally in Wild. In the course of my edits I realized it wasn't necessary to the story, and then a couple months later I was writing a Sugar column and realized it would be the perfect story.

There are Dear Sugar columns in Tiny Beautiful Things that never appeared online. How did you pick which ones would appear only in print?

The first thing I did was look at all of the columns I had written for The Rumpus and put them on my dining room table and try to break them down into topical piles, like "sex" and "romance" and "parenting" and "money" -- all of the different premises, all of the different things I've written about grief and loss.

What was really fascinating about that was so many of them blurred together. The question would very clearly be about grief, for example, but my answer was about grief and something else. They had a universal quality that was very hard to strictly break down into universal subject matter.

But I did that nonetheless. I wanted to have the book be really vast. I didn't want it to be too heavy in one direction. And so once I had those topical piles that were loosely enmeshed in each other, I chose the columns that I wanted to include in the book. That was kind of a brutal choice in some ways.

I wanted to have a range. I wanted to include the reader favorites there in the book of course -- "Write Like a Motherfucker" is in there, "Beauty and the Beast," "How You Get Unstuck" -- several of the big ones that were very viral online. But I also wanted a range of subjects and tone and stuff. So once I made those selections, I [asked], "What are the holes? What haven't I addressed in this so far?" I really chose the other letters with an eye to that.

Some examples of letters that are in the book but never in the column: One is from this woman with an elderly father who is moving into her house with her. She's going to be taking care of him in his old age. He's begun confessing to her all of his sexual exploits, including having cheated on her mother for many years. This woman is just beside herself, because she doesn't want to hear about her father's sexual exploits. So it's this sort of eldercare question: How do I set a boundary with my father about sex now that he's living with me?

Another one is another errant father -- a young woman whose father has left her mother for a much younger woman. She loves her father, but she's having a hard time essentially separating the ways her father wronged her mother from whether her father has wronged her or not; and how to have a relationship with him given what has happened to her parents' marriage.

Another one is a woman whose twenty-something son has moved back home, and she doesn't want him to live in her house. She wants to have her house to herself. She wants to walk around naked and do yoga and stuff. She doesn't want to have to have these boys around now that they're grownups.

Those type of questions, I chose them because I hadn't addressed them already.


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