Before Cheryl Strayed published Wild, her memoir-turned-movie recounting a solo trek along the Pacific Crest Trail, she was best known as Sugar. The longtime advice guru for the Rumpus online literary magazine’s Dear Sugar column, Strayed received scores of letters—at times, 100 per week—and replied with stories from her own life, penning answers just as personal as the questions. Strayed compiled her most poignant responses into a book called Tiny Beautiful Things: Advice on Love and Life from Dear Sugar, and the correspondences became a play adapted by Nia Vardalos (My Big Fat Greek Wedding) and co-conceived with Hamilton director Thomas Kail.

On September 12, Boulder Ensemble Theatre Company (BETC) will begin its season with the show’s Colorado premiere (tickets start at $23), which follows Sugar’s life as she responds to advice-seekers, portrayed by three actors who step in and out of her personal space. “It’s not a book or a play that dances around on the surface of things,” Strayed says. “It’s something you’re experiencing alone in the dark, but also together in the dark.” It’s also a strong opening statement for BETC, whose 14th season focuses on empathy: Tiny Beautiful Things closes on October 12, making way for The Realistic Joneses, a tale about neighbors discovering one another’s private pains.

Before you take your seats, we chatted with Strayed about the process of turning a book into a play and asked her for some advice.

5280: How did the play adaptation come about?
Cheryl Strayed: Tiny Beautiful Things was published four months after Wild. It was a very intense year that those books came out…. One day, on social media, I saw that Nia Vardalos had written on [one of my social media pages]. I DMed her. It was just when Wild the movie was being made, and I was in Los Angeles to see the first cut. We met for tea and talked about the idea. Several months later, the three of us [including Thomas Kail, director of In The Heights and Hamilton] all met up in New York City and began the conversation of how does this book become a play. It’s a challenging concept because usually plays have beginnings, middles, and ends and follow one story, where obviously Tiny Beautiful Things is so many stories and told in the form of letters.

How did you and Nia pick which columns would appear in the play?
That was Nia. One of the things I’ve learned about having your work adapted is you really do have to weigh in about the important things, but the person who’s doing the adaptation, it’s really their interpretation of your work. I trusted Nia. A lot of it was: How many columns can we fit into this play? She had to trim them, and she had to exclude some. She was going for some variety and some emotional response. We needed some humor in there, some that were kind of sweet, some that were devastating. You cry through the play just like the book, but you also laugh. Nia always says to me that adapting the play was the meanest thing she’s ever done because she had to read certain columns she loves and say, “You’re not going to be in the play, sorry.”

When and where did you first see the play?
I was very much a part of the whole process, so I saw it along the way. The first time I saw it as an audience member was in New York City at Public Theater when they did the dress rehearsal. It was very emotional for me. It still is. I’ve seen the play numerous times now in various cities, and I always have this sense of astonishment because I can’t believe that not only has my book been made into a play, but it’s also my life. Sugar is me. It’s really the surrealist experience…. I feel really grateful that my books have inspired other artists to also make art.

What do you hope audiences get out of the production? Is there a theme or a moral or a sense of the world you want them to walk away with?
I love that people who are big fans of the book go, and they feel like they got the same things from the play as they did from the book—that feeling of having an emotional experience and having an experience that is about being courageous in the direction of vulnerability and truth and compassion. It’s not a book or a play that dances around on the surface of things. New people who come to the whole thing first with the play, they get it; they go on that emotional journey too. They find themselves unexpectedly moved or unexpectedly feeling some things they haven’t felt in a long time. When everyone is having an emotional experience at once—I’ve been in several audiences where people are weeping together and you can hear it—it feels like something you’re experiencing alone in the dark but also together in the dark, which is powerful.

Advice columns seem so passé. Why do you think the Dear Sugar column still resonates with so many people?
I think that we always like to know what other people are struggling with. Advice columns offer up a front row seat in total privacy. The person who’s writing the letter is anonymous, but also the reader can find out about other people’s secrets or struggles or sorrows without actually having to sit across the table from that person. You get to just receive what’s often hidden information, things we don’t often talk about with each other openly. It’s always compelling. What problems are other people having? Sometimes we see ourselves in them and sometimes we think, I’m glad that’s not my problem. There’s always that hunger—a hunger for other people’s stories because they help us make sense of our own lives.

How many letters did you receive on average?
It’s hard to say an exact count. Over the span of those years [from the column on Rumpus to the podcast], I would certainly say like 100 a week and sometimes more. Even when I wasn’t actually writing the column. So, 5,000 to 7,000 a year times nine years. [Ed. note: That adds up to more than 45,000 letters.]

What is it about a letter that made you stop and think, I need to respond to this one?
Sometimes it’s just the subject. I didn’t want the columns to just be about love or sex or romance, so I’d look for topical range. Also, if a letter is really well written, it’s much more likely to make it because it’s very difficult to answer a poorly written letter. Often, it’s poorly written in a way that you don’t have all the information you need. If it lacked clarity or it was vague, it was hard to answer it. And the ones that speak to my heart. I trust my intuition. I had a feeling I needed to answer a particular letter, a sense that I had something to say about it.

Your responses are thoughtful and obviously take time. How do you create the space to think and think deeply?
I take my writing very seriously. I never thought of the advice column as this is just this silly thing I’m doing. I put as much into writing the “Dear Sugar” column as I put into anything I’ve ever written. Even in some ways, [I took it more seriously] because I did feel this sense of some of these people I’m answering are really in pain, they’re really struggling. I would make sure I’d thought it through before I hit send.

I wrote most of them, frankly, in the middle of the night after my kids went to bed. I’d stay up all night writing the column; the next day it’d be up on the website. It’s contrary to the way I usually work, which is to sit with the piece for a while before it’s done. I would think about people’s problems for a while and then begin to write the letter. I’d ponder, sometimes for days. There’s still all this discovery with the act of writing.

Why do you include so much of yourself in your responses to readers and listeners?
When I think about what is the most helpful and most consoling to me when I’m in some sort of trouble, I often turn to books, poems, and stories. I want to know what other people who have experienced something like that, how they’ve dealt with it. I’m simply using stories to illuminate the questions. It’s a powerful force, stories. In the writing we love most, we find ourselves even if that other is a completely different person, different age, different gender, different everything. When we see the truth of their existence, we feel less alone in ours. I tapped into that. That’s what I trusted, and that’s how the column was written.

What makes you well-suited to the role of Sugar, to answering the questions of such a diverse audience?
With nothing but doubt. Who the hell am I to give advice and write a column? There’s no such thing as somebody who’s qualified to give advice. We’re all qualified to give advice. We all get advice from a number of different sources: parents, strangers, therapists. None of us finds our way on one authority that has some sort of qualification to tell us how to live. We find it in books, we find it in songs. I embraced [that] I’m just one of those sources in the form of this column and I’m going to do my best. It’s not necessarily going to be the thing that unlocks anyone’s struggle, but what I hope it will do is make them feel less alone and help them find a new way forward.

What’s next for you?
I’m writing my next book. It’s another memoir.

Leave us with a piece of advice. What’s your truth today?
I tell my kids this all the time: “The closest thing you can get at any given moment to either telling the truth or living the truth—or both preferably—the happier you’re going to be.” None of us are ever happy when we’re covering up or denying. The way out of our anxieties and worries and struggles is to be as honest with each other and ourselves as we can bear to be. Once we tell the truth, we’re released from the tyranny of secrecy but also of pretending otherwise. When you say, You know what? I’m not happy in this relationship. Or, I don’t like this job. Or, I am in love with you. Or, I do want to be a painter instead of an attorney—the minute you acknowledge that to yourself and the world, you let all this possibility in, this possibility that’s going to take you in the direction of joy and satisfaction and real life.

This article was originally published in 5280 September 2019.
Daliah Singer
Daliah Singer
Daliah Singer is an award-winning writer and editor based in Denver. You can find more of her work at