Cheryl Strayed published her first column as "Dear Sugar" on March 11, 2010, on the website The Rumpus. The column predated her and had formerly been written by Steve Almond. When Strayed took over, she noted that a new writer would be now be responding to reader questions, but did not reveal her name or anything about her identity. For almost two years, Strayed wrote the column anonymously, revealing small hints about her life and history. In February 2012, she formally revealed her identity as "Sugar" at a "coming-out party" event in San Francisco. This reveal co-coincided with the release of Wild, which was published in 2012.
The "Dear Sugar" column continued to run until May 2012. A selection of columns was published in book format in 2012 as a collection called Tiny Beautiful Things. Between 2014 and 2018, the column lived on in podcast format. In a show called "Dear Sugars," Strayed and Almond would respond to listener questions. Topics of both the web column and podcast were notable in expanding the scope of what a typical advice column would have previously covered: letter writers disclosed intimate fears, hopes, and desires, asking big-picture, existential questions. In return, Strayed wrote lengthy answers in which she both engaged deeply with the context of the letter and shared her personal experiences.
Strayed has explained that she had just submitted the first draft of Wild when she was invited to begin writing the column. Many themes—such as loss, loneliness, self-acceptance, and self-compassion—are shared across both types of writing. Her experience with the "Dear Sugar" column likely helped to cultivate a receptive audience for Wild when it first appeared.