Cheryl Strayed talks ‘Tiny Beautiful Things,’ advice columns, and radical empathy

St Louis Magazine interview with Cheryl Strayed, July 14, 2021

Max & Louie Productions returns to the stage July 29 with Tiny Beautiful Things, based on Cheryl Strayed’s popular and deeply revealing Dear Sugar advice column. Strayed, who at first wrote the column anonymously on, is also known for her memoir Wild and the movie adaptation starring Reese Witherspoon. Oscar nominee Nia Vardalos, who wrote and starred in My Big Fat Greek Wedding, adapted the columns for the stage from Strayed’s book Tiny Beautiful Things: Advice on Love and Life from Dear Sugar.

St. Louis Magazine caught up with Strayed to discuss the play, the column, and how the more things change the more they stay the same.

What’s it like seeing your columns performed onstage?

It’s so astonishing, really, because Dear Sugar isn’t just a regular old advice column. It’s sort of a memoir hybrid. I receive very often a very intimate letter from somebody seeking advice. That person is often telling a secret, confessing their deepest sorrows. I write them back with a very similar tone—I tell them stories from my life by way of illuminating the question they’re asking me. Both the adaptation of the play and the adaptation of Wild to the screen, it’s the most surreal experience of my life—very strange to watch an actor tell stories about some of the most painful things I’ve lived through and the most beautiful things I’ve lived through as well.

How involved were you with Vardalos’ process of adapting the book to the stage? Did you choose the letters?

I was involved in that process, I talked to her a ton, and I gave her feedback and thoughts, but, in the end, she chose the letters. There are letters that you’d think you’d put in the top five or 10 of the most well-known Sugar letters—they’re not in the play. Nia had this incredibly difficult job of trying to form a story arc. She had to consider, What is the shape of the performance? Because I had gone through the experience with Wild, I knew how to go through that and be the fairy godmother. I love that she chose a range of incredibly hard and powerful letters.

The letters are anonymous—how did you get permission to use them for the book?

The legal team was like, “Waaaait a minute, what about all these letters. You need permission!” I didn’t have most people’s email addresses—they’re writing to me through the Dear Sugar portal—it’s anonymous. I had to put a little notice up on the Rumpus website, and I sent it to a Sugar list, and I said, “Hey, if you’re one of the people who has written to me, would you please email this statement?” And what was funny was that every single person did. I was so touched by that—how much it meant to them that their letter would help someone else, this incredibly intimate epistolary exchange. It’s like therapy in the town square. It can be powerful and transformative simply to hear the letter of someone expressing what you feel or what you felt you couldn’t say.

How do you think concepts like radical empathy and earnestness have changed or come to the forefront during the pandemic?

I’ve been writing the Dear Sugar column in different forms—the column, the book, a couple of podcasts, a Substack newsletter—for more than 11 years. Every one of those years, it’s like, “Now more than ever, we need this!” I’ve never been interviewed by anybody who didn’t ask that. Absolutely more than ever, but I think it’s more important than ever to remember: Hard times come, they will keep coming, they will come again. The unexpected beauty of difficulty is that it gives us very often a deeper perspective about how important it is to honor friendships, honor love, honor connections. Honor that voice inside that says “What I feel matters.” We went through a collective reckoning with the pandemic—a lot of people turned inward.