From Advice to the Screen and Everything in Between March 20, 2026
When Cheryl Strayed was asked to take over the “Dear Sugar” advice column, little did she know that her “yes” would change her life. Her vulnerable and empathetic essays, based on her personal experiences, guided letter writers through the darkest moments of their lives. Strayed’s intimate anecdotes captivated audiences and were collected into the book Tiny Beautiful Things, which, in turn, was adapted into a television series and this play.
From an Advice Column…
“Dear Sugar” was an anonymous advice column (originally written by Steve Almond) published on The Rumpus website from 2008-2012. Strayed wrote a congratulatory note to the columnist, and in 2010, Almond asked her to voluntarily assume the role of “Sugar.” She accepted the offer after a momentary hesitation. Over the course of two years, Strayed wrote over 70 heartfelt letters to advice-seekers across the country, attracting tens of thousands of fans who resonated with her writings. She eventually revealed her identity to the public in 2012, shortly before releasing her best-selling memoir Wild.
To Best-Selling Novel…
Soon after “Sugar” was known as Cheryl Strayed, she released a collection of 61 “Dear Sugar”
letters in the book Tiny Beautiful Things. Most of the book’s letters were originally published in The Rumpus, along with a few never-before-seen entries. Tiny Beautiful Things debuted at No. 5 on the New York Times Bestseller List in the advice and self-help category and sold over 100,000 copies by 2014. Within this readership was writer Marshall Heyman, who shared the book with director Thomas Kail, who passed it along to actor and writer Nia Vardalos. These three artists felt that Strayed’s words had the potential to be brought to the stage.
To Globally Produced Play…
Heyman, Kail, and Vardalos connected with Strayed through social media, met for tea, and created an agreement to produce Tiny Beautiful Things for live theater. Each of them came with their own accolades: Heyman had written scripts for Netflix and HBO, Kail directed the original productions of Hamilton and In the Heights, and Vardalos starred in and wrote My Big Fat Greek Wedding. The theatrical production of Tiny Beautiful Things (adapted by Vardalos and co-conceived by this all-star group) premiered in 2016 at The Public Theater with a sold-out run and an encore production the following season.
Vardalos masterfully condensed two years of Strayed’s writings as “Sugar” into one evening while preserving the integrity of the original work. The play includes back-and-forth exchanges between the author and letter writers, an element not explored in the previous advice column formats. Additionally, bringing live audiences together to experience these real stories creates another layer of intimacy to this already emotional journey. This production has clearly struck a nerve with viewers as it is frequently performed across the globe, leading to its adaptation for the screen by Cheryl Strayed and television producer Liz Tigelaar.
To Emmy-Nominated Hulu Series…
In 2023, eight episodes of Tiny Beautiful Things premiered on Hulu featuring a protagonist named Clare whose life is falling apart. This fictionalized depiction of Strayed’s life explored real aspects of her younger self (played by Sarah Pidgeon) and an alternative reality of her present self (played by Kathryn Hahn). The show blatantly highlights the irony of an imperfect person offering advice and exposes the collective need for connection. Kathryn Hahn and Merritt Wever’s raw performances as daughter and mother resulted in their respective Emmy nominations as Outstanding Actress in a Limited Series.
Tiny Beautiful Things is a mosaic, collectively written by scores of advice seekers and artists
While Tiny Beautiful Things has taken many artistic forms, the power of Strayed’s words and experiences remain the same. Her advice comes from a lifetime of adversity. Strayed had the courage to overcome and reveal the deepest parts of herself to show others that they are not alone. Her life-changing “yes” reminds audiences that everyone has something to offer, no matter how tiny, and it is oftentimes beautiful.