credit Holly Andres

Horizontal Advice with Cheryl Strayed

By Constance Roisin

Constance Roisin talks to Cheryl Strayed about love, sense of self and agony aunts.

Tiny Beautiful Things, which aired earlier this year on Hulu, has a unique premise. Clare, an anonymous agony aunt (played brilliantly by Kathryn Hahn), shares the same past with real-life Dear Sugar author Cheryl Strayed. Her present, on the other hand, is entirely fictional. The separation between the two women rests on the idea that, unlike Strayed, Clare never hiked the Pacific Crest Trail and never wrote the bestselling memoir Wild. “The hike was in so many ways this moment in my life where I really had a final reckoning,” says Strayed. Clare, however, “never did follow through on her deepest intention, to be a writer. I think so much of the show is about that. Like, well, what happens when we don’t listen to the inner call.” Whilst watching flashbacks – scenes lifted from Strayed’s own experience of losing her mother young – was “very surreal”, in the case of the Kathryn Hahn scenes “I could just sit back and relax. That’s not me.”

Strayed’s Dear Sugar column (published monthly on Substack) isn’t just advice, “It’s literature, I’m writing an essay, and so I’m crafting a piece of art.” The essays are often deeply personal, counter to the conventions of a typical agony aunt. Take, for example, this letter to a person who had written simply “WTF, WTF, WTF? I’m asking this question as it applies to everything every day.” Strayed’s response begins, “My father’s father made me jack him off when I was three and four and five. I wasn’t any good at it.” And it concludes, “Ask better questions, sweet pea. The fuck is your life. Answer it.” Is this how she gives advice to her own friends? With the column, “there are consequences for me if I give terrible advice”, Strayed laughs, “and they write to me later and say you ruined my life (which has never happened), but it’s not like it’s had an impact on our friendship.” For example, one of the most common questions asked is: should I stay or should I go? “Seldom would I say with real clarity absolutely you should leave, whereas I might do that in my column. But then you’re friends with someone who says to their husband: Cheryl says I should leave you. Well, you’re never having dinner with that couple again.”

Strayed is often direct, famously so in her column Write Like a Motherfucker: “The most fascinating thing to me about your letter is that buried beneath all the anxiety and sorrow and fear and self-loathing, there’s arrogance at its core.” This is quintessential Sugar. “The value that I hold really very seriously at the centre of my work as Sugar is that I don’t think that honesty is in opposition to kindness and love. And I think that there is a way to say to somebody that you are not seeing this accurately, you’re not seeing this clearly, you’re creating barriers that don’t exist. Whenever I’ve pointed out anything to anyone like, you’re being arrogant, it’s because I have identified that in myself as well.”

There is nothing an agoniser can say that will shock Sugar. “So much advice is framed as the advice-giver is up on this side of the fence: the one who knows, the one who has achieved the highest version of the self, the best version of the self, and then here she is from that elevated position saying here’s what all the rest of you should do.” In contrast, “I’m always down there in the mud with the person asking the question. I think of it as horizontal advice. I also struggle, and I’ve also failed, and I’ve also made mistakes. I’ve also been arrogant and stupid and misinformed and confused and fill in the blank. And I will be all those things again.”

Sugar has golden rules that are the bedrock of her advice: You can’t make someone love you, Self-pity is a dead-end road, No is the kind of power the good witch wields. Is there something that unites her advice with Wild and her novel Torch? “I think a thread through so much of my work is that kind of affirmation, if you will, that life is hard, and life is struggle, and life is suffering, and life is also beauty and love and resilience and redemption and that I do believe that we can walk the hardest paths and make our way eventually to the bridge or the mountaintop. Or maybe just a more solid sense of self.”


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