On March 11, 2010, an anonymous writer introduced herself as the new voice of “Dear Sugar,” an advice column on the Web site the Rumpus. Sugar claimed she would offer a combination of “the by-the-book common sense of Dear Abby and the earnest spiritual cheesiness of Cary Tennis and the butt-pluggy irreverence of Dan Savage and the closeted Upper East Side nymphomania of Miss Manners,” but soon proved to be something entirely her own: an advice columnist who spoke through frank personal experience, one whose responses went from advice to essay and back again. In The New Republic, Ruth Franklin called her “the ultimate advice columnist for the Internet age, remaking a genre that has existed, in more or less the same form, since well before Nathanael West’s acerbic novella ‘Miss Lonelyhearts’ first put a face on the figure in 1933.”
Over the next two years, Sugar’s fans—a devoted readership that includes more than fifteen thousand Facebook and Twitter followers—learned bits about who she was. She was a she. She had lost her mother far too early. She had children, a husband, student-loan debt, and a seemingly inexhaustible supply of open-minded, honest advice. Her responses covered jealousy, the decision to have (or not have) children, drug addiction, and the unanswerable questions of life. On Tuesday night, at a coming-out party in San Francisco, Sugar formally introduced herself as Cheryl Strayed, a writer living in Portland whose new memoir, “Wild,” will be the Rumpus Book Club’s pick for March. She recently took time to answer questions on anonymity, intimacy, and her relationship with her readers. An edited version of the exchange appears at newyorker.com.