Cheryl Strayed · Sugar

Cheryl Strayed / Sugar is the writer and advice columnist whose public voice emerged from a tension between persona and testimony: Sugar began as an invented character, but became most consequential when Cheryl Strayed / Sugar answered strangers by bringing her own history into the exchange. The columns gathered in the book are intimate encounters between largely anonymous correspondents and a writer who increasingly treated candor not as decoration for advice but as its basis.

Origins and the Sugar persona

Before there was Sugar, Stephen Elliott had an idea for an online literary community, The Rumpus. He enlisted impoverished writer friends, including Cheryl Strayed / Sugar, to help build it. Her contribution was an advice column, first proposed under the joking name Dear Sugar Butt, an endearment Stephen Elliott and Cheryl Strayed / Sugar had used in email correspondence; it was shortened to Dear Sugar. The project began, then, in friendship and in the search for a worthwhile distraction, rather than as a conventional professional appointment.

Taking on the column was an act of confidence. Cheryl Strayed / Sugar wanted it to be irreverent and brutally honest, but at first conceived Sugar as a persona: a woman with a troubled past and a slightly reckless tongue. Sometimes the character felt real, and Cheryl Strayed / Sugar could feel herself entering into the pain of the people who wrote. More often, she says, wit filled the space where emotional connection did not. After a year of writing columns quickly, she quit. That early failure matters to the character’s history: the voice that later became known for radical candor did not begin as a settled expression of the writer’s self.

From performance to testimony

The change came after Cheryl Strayed / Sugar read a nonfiction piece by Cheryl Strayed. She already knew Cheryl Strayed as the author of the novel Torch; the essay’s account of infidelity and mourning gave her a strong intuition that Cheryl Strayed could take over the column. The invitation was strikingly impractical. Cheryl Strayed had two small children, substantial debt, no regular academic job, and would receive no pay for the work. Stephen Elliott nevertheless asked her to do it, in part because Cheryl Strayed had once sent him the only fan letter he had received as Sugar.

The decisive answer came in response to a letter from someone signing as WTF, who asked the same question repeatedly. Cheryl Strayed / Sugar began her reply by disclosing that her grandfather had sexually abused her when she was three, four, and five. He babysat her and her sister a couple of times a week; when the children were trapped in his house with him, he exposed himself and made her touch him. She recalls understanding that she did not want to comply, while also believing there was nothing she could do. The reply refuses the familiar advice-column distance in which the columnist attends only to the correspondent and offers reassuring generalities. Instead, the writer makes her own history part of the answer.

The disclosure also gives the column a before and after. As a child, Cheryl Strayed / Sugar moved far away from her grandfather shortly before turning six. Soon afterward her parents separated and her father left her life; she never saw her grandfather again. He died of black lung disease at sixty-six, when she was fifteen. She felt neither sadness nor happiness at his death, describing him as no one to her while also recognizing that what he had made her do continued to move through her. For years she said nothing, hoping silence might erase the abuse or reduce it to an invention. The act of writing breaks that silence without pretending that the past has vanished.

A later image makes that return bodily and difficult. While tending to an injured bird that would not die easily, Cheryl Strayed / Sugar felt its movements through a paper bag and recognized a resemblance to the sensations associated with her grandfather. This time, she understood what she was doing and pressed harder to end the bird’s suffering. She names the act as both murder and mercy, then answers WTF’s question by insisting that the question belongs to her own life and that the correspondent must answer for his. The reply turns private memory into a demand for more exact self-knowledge, not a license to treat every question as equally meaningful.

Grief as the ground of her counsel

In answering Johnny’s question about the meaning of love, Cheryl Strayed / Sugar returns to the death of Cheryl Strayed’s mother. Her mother was alone in a hospital room when she died, and Cheryl Strayed / Sugar was not there. The final exchange remained painfully specific: her mother could not bear the pain of being touched, so she said, “Please, no,” when Cheryl Strayed / Sugar bent to kiss her. Cheryl Strayed / Sugar said she would return in the morning, got her coat, and told her mother, “I love you.” Near the door, her mother managed one last word: “love.” Cheryl Strayed / Sugar returned the next morning to find her dead.

For years, the absence hardened into a repetitive reckoning with the decisions that had kept her from her mother’s last hours. Thinking through those choices did not change what had happened. Yet the mother’s last word continued to sound within her, and Cheryl Strayed / Sugar identifies the memory as Sugar’s genesis story and as something underlying every answer she gives. The column’s account of love therefore begins not with a definition at a distance but with an irreversible farewell: a final word that is incomplete as a sentence yet sufficient as an expression of care.

The same approach shapes her response to Living Dead Dad, whose son was killed when a driver ran a red light. Cheryl Strayed / Sugar does not claim that consolation can restore the son or undo the circumstances of his death. She acknowledges the bereaved father’s rage, suicidal thoughts, and imagined future for his son, then directs attention to the love that remains his own and cannot be taken away. Her account of her mother’s death serves as testimony for this argument: grief does not disappear, but love can be larger than bitterness and can help a person survive the next day. The advice offers neither a cure nor a timetable; it recognizes that the bereaved person must make a life in a world transformed by loss.

Advice, audience, and narrative role

The book presents Dear Sugar as a collection of exchanges between strangers. Many columns first appeared on TheRumpus.net, while others appear in the book for the first time. Correspondents wrote through an anonymous form on The Rumpus or directly to Sugar’s email address; most did not know that Cheryl Strayed was Sugar, and she generally did not know who they were. Some letters were lightly edited for length or clarity, but most were published as their writers had sent them. Cheryl Strayed / Sugar selected letters according to what interested, challenged, or touched her, and says she tried to give the best advice she could think of.

Her advice can be tender and severe in the same breath. To Seeking Wisdom, who worries about being fat, Sugar rejects the premise that a round stomach deserves sustained lament and tells the correspondent to feed herself. She then turns to a charged memory from the correspondent’s twenties: a best woman friend crawls naked into bed, straddles her, and warns that she should run before being devoured. Sugar’s instruction is to believe the friend. The shift from blunt reassurance about the body to an alarming intimate encounter shows the column’s range, while its directness echoes the early ambition to combine irreverence with honesty.

Across these exchanges, Cheryl Strayed / Sugar’s authority comes neither from anonymity alone nor from presenting herself as untouched by the problems she addresses. The correspondent’s letter supplies one account; the answer may bring in the columnist’s remembered experience, changing the exchange from a one-way delivery of advice into a personal act of witness. Her disclosures do not make the strangers’ situations identical to her own. Instead, they show how a remembered wound, a mother’s last word, or the continuing force of grief can become material for thinking alongside another person. Sugar’s significance lies in that movement: a persona first used to perform advice becomes a voice willing to risk telling the truth that the advice depends on.