Cheryl Strayed’s ‘Dear Sugars’ Podcast is Totally Addicting

A podcast for the "lost, lonely, heartsick," and everyone in between.

Cheryl Strayed is my therapist. Every morning without fail, while I’m brushing my teeth or waiting for the subway, she dispenses hard-earned wisdom straight into my ear. She is vulnerable, funny, judicious, and blunt with her advice. I’m at the point where I can’t start my day without checking in with her first.

Okay, so obviously the best-selling author of Wild, a memoir that was adapted into an Academy Award-nominated film where Strayed was played by none other than Reese frickin’ Witherspoon, is not actually my mental health professional. But her podcast, “Dear Sugars,” in which Strayed and her co-host Steve Almond answer letters from the “lost, lonely, and heartsick,” has become an essential and treasured part of my daily routine.

cheryl strayed justine goode dear sugars

Please note that Cheryl Strayed herself liked this tweet, so we are basically best friends.

I am not the first devotee or beneficiary of Strayed and Almond’s sage advice—far from it. “Dear Sugar” began as a column, penned anonymously by Almond on the literary site The Rumpus. Strayed took over in 2010 before “unmasking” herself in 2012, the same year Wild was released. Strayed then published Tiny Beautiful Things: Advice on Love and Life from Dear Sugar, a compilation of her columns, which Vulture heralded as “some of the most surprising, raw, and heartbreaking writing on the internet.” Like a literary Pokemon, the “Dear Sugar” column has evolved, strengthened, and shape-shifted over the years: the podcast is simply its most recent and vibrant iteration.

Since its pilot episode in December 2014, the Sugars have tackled dozens of thorny topics including addiction, abusive relationships, secret pasts, sexless marriages, and dating in the digital age. Unsurprisingly, Strayed and Almond handle their readers’ letters with immense empathy and thoughtfulness. Rarely is there even the tiniest tinge of judgment present as the co-hosts navigate the nuances of each letter with open minds and hearts. The only time I really heard a host come down on a letter writer was when a young man asked, in complete earnest, if it was bad that he had told his girlfriend that her recent weight gain “bothered” him. Strayed did not have time for that.

Cheryl Strayed Roxane Gay 2018 Best American Series Guest Editors

READ: CHERYL STRAYED, ROXANE GAY NAMED GUEST EDITORS FOR 2018 BEST AMERICAN SERIES

The entity of “Sugar,” in column, book, and/or podcast form, has been described as “all-knowing,” or even an “oracle” for the modern age. But one of the things I love most about the show is the fact that Strayed and Almond are very up-front about what they don’t know. Almost every episode features a guest who can shed more light on the topic at hand: for example, writers Ashley Ford and Lindy West both shared their experiences dealing with weight discrepancies in romantic relationships (“Body Weight and Romance” and “The Weight of Love”). Comedians Cameron Esposito and Rhea Butcher discussed queer relationships (“Making Love”), and in a particularly wonderful three-part series, preeminent sex therapist Esther Perel answered letters about betrayal and mismatched libidos (“The Infidelity Episodes” and “Sexless Relationships”).  And oh yeah, Oprah Winfrey and Hillary Clinton stopped by to talk about, respectively, the power of saying “No” and the double-bind of female ambition.

There is also the strong sense that, despite being characterized as modern-day sages, Strayed and Almond are very, very human. They are wildly honest when it comes to discussing their own lives, and are constantly diving headfirst into personal discussions—about sexual fantasies, drug use, depression—in order to destigmatize and diffuse the shame or guilt expressed by letter writers. Their candidness is refreshing and unapologetic, and even though I now know more about either of these strangers than I ever wanted to, I kind of love it.

For example, in an episode discussing the effects of pornography on young men, Almond came across as a world-weary veteran of the internet’s offerings, while Strayed was obviously less well-versed: she kept referring to “porn movies,” suggesting a Boogie Nights kind of production, and seemed genuinely shocked to find that 1 in 3 young women watch porn online. Their disconnect on the subject, and the charming awkwardness that arose, reinforced the show’s sense of authenticity and lack of ego.

It’s small, unpolished moments like these that keep me listening, because in addition to the intrigue and catharsis of hearing difficult personal problems being broken down on air, we get to actively witness the a dissolution of the mystique that often surrounds successful authors. Obviously, with the publication of Wild, Strayed made her life more or less an open book, but Dear Sugars gives us a glimpse into an even rawer, simpler, and sweeter side.

Dear Sugars is available on iTunes, Google Play, Stitcher, and any other podcast streaming platform. 

Justine Goode
the authorJustine Goode
Contributing Writer
LA-born reader. English major. Liberal with em-dashes.