• 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."

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.

How has baring yourself in a memoir affected your motivation to continue writing an advice column? Does it feel less pressing these days?

I wrote Wild before I became Dear Sugar. I was always working in that vein of being really honest and self-revealing. When I was about to reveal myself as Sugar, one of the pleas from people who didn't want me to reveal myself was, "You won't be as open with your column once we know who you are." I always said no, no, no, you're mistaken about that." Because as Cheryl Strayed I am every bit as open as I am as Sugar, and I always wrote the Sugar column, in my own heart, as Cheryl Strayed.

I knew someday my name would be on those columns. I never thought the anonymity was a way of protecting myself, so I didn't use it as such. I just think that to write this work is to be revelatory and to be open and honest.

Even in my [first] novel, Torch, I was always seeking the deepest truth. Sometimes that's literal and sometimes that's figurative, you know? That big Truth with a capital "T."

They're very different forms, those two books, Wild and Tiny Beautiful Things. I felt like it was really fun for me actually, after having been so deeply enmeshed in this traditional memoir form, to try something new -- to cross the boundaries of non-fiction via an advice column.

Do most Dear Sugar readers address you as Cheryl or Sugar now?

Most people respect that Sugar persona and they write to Sugar. Sometimes I've gotten some -- not to my email address, but to the Dear Sugar email address -- that say, "Dear Sugar/Cheryl." But if I chose one of those to go up on The Rumpus, I would edit out "Cheryl."

"Cheryl" will never appear in the column, or "Brian," or "Portland." I will always maintain, like I said, that language of "Sugar Land." I love that I created this narrative -- non-fiction, because it is about my life -- but I don't mention specifics when it comes to the place, or the name of the person. I write about it in more general terms.

You've mentioned before that you didn't read advice columns before starting this one. Do you read them now?

Frankly, I've been so busy. All I'm reading right now is the seven hundred books I've been asked to blurb. I don't read any advice columns regularly -- even still. When I do read an advice column, it's Cary Tennis (of Salon), who I just think is lovely and wonderful. Or (SF Weekly editor) Anna Pulley, who also is lovely and wonderful. And Dan Savage (The Stranger), who is always good for a great laugh. The advice he gives about sex is always so fun to read.

Those three are the ones that I most commonly read, but to be honest with you I can't remember the last time I read any of their columns. It's been a few months. I can't even manage to read my own email these days, let alone go online and tool around and have fun. 

• Strayed with Oprah

Your memoir, Wild, recently revitalized Oprah's Book club. No small feat. 

She just called me up one day out of the blue on my cell phone. She says, "This is Oprah." My publisher didn't know she was going to call me. She called me first. We just had this great conversation. She loved Wild.

I have so much admiration for Oprah for so many reasons -- I mean she's such a self-made woman and she's worked so hard. But what I admire most, I think, is that she's always worked really hard out of her passion. She does things because she loves them.

I went to stay with her at her place in Santa Barbara. I could just see in her eyes that she chose Wild because she just really liked Wild, you know? It wasn't some committee that pressed it on her or something. I just thought that was incredibly cool, and for me as a writer that was terribly flattering. To see that she connected with the book and decided to restart her club because of it -- it's been an amazing time.

It was really something. I'll never forget it. I kept saying to her when she was talking to me -- I kept shrieking, "Are you kidding me?! Is this a joke?! Is this candid camera or something?!"

You're 43 now. I think one thing that's endeared you to so many readers -- and writers -- is the fact that your career took off kind of late. Talk about how you value the accumulation of life experience when it comes to writing. 

It's fascinating to me -- this experience of having Wild be met with such success in the marketplace. Torch was published when I was 37, and it received wonderful reviews and critical acclaim, and it sold well for a novel by a first-time writer. It wasn't a national bestseller or any sort of sensation. I felt incredibly pleased with what happened with Torch, but I was still in this rather small pond, and comfortable there.

If you had gone back in time and said to me "If you choose this flower, you could have the sort of success with Torch that you'll have with your second book," I would have said "I want it to happen with my first book." Because we all want that, right? We're all looking for that kind of external affirmation.

But I'm so glad. I think that success too early never turns out well. Part of it is that you start focusing on the wrong things. I've been a serious writer now for 23 years, and once I got over those grandiose feelings of "I want to be famous," and "I want to be rich" -- once I got over that, which I got over pretty quickly, what I really settled on was that the work was the reward. That the work experience of writing, of having that feeling, what it feels like to finish a book that you've toiled away on for years, to feel that is a success. To have that achievement, I think that is what has sort of grounded me through all of this craziness that happened with Wild.

I'm really excited about what's happened with Wild, and it's beyond anything that I ever really dreamed. It's not that I made my dream small, but I realized pretty early on that that can't be the measure of success for artists. Outside stuff happens sometimes, and it doesn't happen sometimes, and it doesn't really have a direct relationship to the quality of the work.

I guess I just keep faith with the work. That's something I say as Sugar a lot: Keep faith with the work. Keep faith with the work. And I do. I only could have done that after writing by myself for all of those years and having to constantly seek that assurance from within, instead of getting it from an external source.

Now that I am getting it externally, I'm not taking it too terribly seriously. I'm just going to keep doing what I've done. I'm just going to write another book.

That book could be just totally ignored, but I'm going to write it anyway.