Sugar predates Cheryl Strayed. In fact, Strayed’s future cohost of the Dear Sugars podcast, Steve Almond, became the first Sugar in 2009, when his friend Stephen Elliott founded The Rumpus, a largely volunteer-run online literary and culture magazine. At that time, Almond, who aimed to adopt the persona of “a woman with a troubled past and a slightly reckless tongue,” found that he failed in his endeavor as an advice columnist because he over-relied on wit “where [his] heart failed [him]” (3). However, after reading Strayed’s brutally honest essay on infidelity and mourning, he felt that he had found the real Sugar and asked her to take the unpaid job in early 2010. Strayed’s brand of advice soon distinguished itself from the correspondent-focused content of the typical columnist guru, which models itself on the dynamic of traditional therapy, where the therapist remains a featureless receptacle for the patient’s problems. Instead, Strayed sought to radically empathize with those asking for advice by telling them stories of her own experiences, with the hope that it would enable them to better understand their predicament.

Thus, while Strayed remained anonymous for her two-year term as The Rumpus’s Sugar, readers felt as though they got to know her personally over time.