67 pages 2 hours read

Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

Nonfiction | Essay Collection | Adult

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Background

Literary Context: The Dear Sugar Column and Its Impact

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. This is evident, for example, in Living Dead Dad’s pronouncement that he is writing to Sugar “because the way [she’s] written about [her] grief over [her] mother dying so young has been meaningful to [him]” and even his conviction that “if anyone can shed light into [his] dark hell, it will be [Sugar]” (279). Here, Living Dead Dad feels that Sugar is uniquely placed to help him, owing to her combination of distance from his life and her ability to voice aspects of the grieving experience that are painfully true and seldom discussed. Correspondents’ anonymity is also important in erasing the particulars of social class, ethnicity, and, on some occasions, gender, which prevent people from easily identifying with one another. While a few people use a variant on their names—for example, Johnny the divorcé, who wonders when he should tell his girlfriend he loves her, or Elissa Bassist, the aspiring writer—most opt for pseudonyms that typecast their problems. One example is Undecided, for the 41-year-old man who wants Sugar’s help in clarifying whether he wants to have children (242). Here, the pseudonym gets straight to the heart of the problem and permits readers who are torn between two competing choices to relate to this man and learn from Sugar’s advice to him. On a few occasions, Sugar further anonymizes her correspondents when she looks beyond their pseudonyms and addresses them collectively as “Women” to answer their letters on similar themes in tandem because they can learn from each other’s examples (169). She also reserves this treatment for the women on two sides of a love triangle with a man Sugar calls “The Foxy Fellow,” who by some striking coincidence both write to Sugar seeking her advice (329). Sugar’s increased involvement in strangers’ intimate dynamics indicated that she was becoming a household name and that people were having parasocial relationships with her even in her anonymity.

In 2012, with the publication of Tiny Beautiful Things and the soaring success of her memoir, Wild, Strayed’s anonymity as Sugar was sacrificed. Indeed, the concrete detailing of her life in Wild, along with increased media appearances and the movie Wild with Reese Witherspoon in 2014, made Strayed a recognizable figure in the public imagination. In the next iteration of Dear Sugar, the podcast Dear Sugars, which began in 2014, people were seeking guidance not just from an anonymous Sugar but from Cheryl Strayed, a household name.

Still, an examination of the more recent columns in Part 6 of the 10th-anniversary edition of Tiny Beautiful Things shows that not much has changed in Strayed’s style of advice-giving since her loss of anonymity and rise to fame. Strayed’s advice to Twenty-Five, the young woman who is squandering her dreams in favor of a meaningless existence, mentions that departure from one’s comfort zone is essential to becoming a more authentic person—and that this was what made her hike the Pacific Crest Trail, the experience that informed her best-selling memoir, Wild. Twenty-Five might be inspired to action by the marvelous outcome of Strayed’s taking initiative; however, Strayed’s overall advice—that it is up to an individual to change their lives—has not changed in her transition from anonymity to renown. Thus, Sugar remains a consistent figure in readers’ minds, despite the various iterations of the woman behind her.

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