Sugar

Sugar is the voice at the center of the Dear Sugar advice column: first a deliberately constructed persona, then the name under which Cheryl Strayed answered strangers with candor grounded in her own life. The column’s defining tension is between performance and intimacy. Sugar can be funny and blunt, but her most consequential answers draw their force from memories of loss, difficult love, and the ordinary upheavals of raising children.

Identity and Origin

The name began as a column on The Rumpus, the literary website Stephen Elliott proposed building with help from his writer friends. Steve Almond, one of those friends, suggested an advice column and initially called it Dear Sugar Butt, after a joking endearment he and Stephen Elliott used in email. The title was shortened to Dear Sugar. Almond imagined Sugar as a woman with a troubled past and a reckless tongue, a persona meant to make room for advice that was both irreverent and brutally honest.

That invention did not immediately produce the intimacy he wanted. Almond later acknowledged that he sometimes reached his correspondents’ pain but more often substituted wit when his heart failed him. After writing columns for a year, he quit. Around that time he read an essay by Cheryl Strayed, whose novel Torch he already knew, and asked her to take over as Sugar. Strayed had two small children, substantial debt, and no regular academic job; the column paid nothing. Almond nevertheless made the request, in part because Strayed had written the only fan letter he had received as Sugar.

Under Strayed, Sugar is both a public voice and a way of telling personal history. The book identifies itself as a selection of Dear Sugar columns, many first published on The Rumpus website and others appearing there for the first time. Letters arrived through an anonymous form or directly by email; most writers did not know that Sugar was Cheryl Strayed, and most were themselves unknown to her. Their exchanges therefore join private disclosures to a deliberately public act of response.

A Voice Built for Directness

Sugar presents herself as willing to answer letters about love, grief, money, and family so long as they interest, challenge, or touch her. Her voice is not simply a persona’s cleverness: it is a method of getting past evasions. In answering a woman who wants to preserve a friendship with a man she loves, Sugar names the relationship as a concealed romantic entanglement rather than accepting the letter writer’s preferred description of it as friendship. She lays out different possible courses, while pointing out that whether the man leaves his girlfriend is not within the correspondent’s control.

The bluntness is paired with an insistence on self-scrutiny. In another answer, to someone seeking practical help finding love, Sugar turns the focus toward readiness: whether the writer can give and receive love, be transparent and sincere, and stop withdrawing from the vulnerability she wants to overcome. Her counsel moves from diagnosis to action, asking the correspondent to meet other people without concealing herself and to extend the same openness to them.

Sugar also distinguishes intensity from intimacy. To a correspondent caught in a painful relationship, she argues that emotional turmoil and scarcity do not establish a deep connection, and that remaining in a relationship that fails to meet one’s needs can both perpetuate misery and close off other possibilities. Rather than pretending that a clean answer is easy, she draws on a poem by Adrienne Rich that has accompanied her for twenty years: its closing thought is a choice to love with intelligence. Sugar offers that idea not as a guarantee of a painless outcome but as a way to ask what a more deliberate life might look like.

Personal Memory as Evidence

Strayed’s Sugar makes personal disclosure part of the argument. In a reply to Johnny, she recalls that the last word her mother spoke to her was love. Her mother was gravely ill and too weak and confused to say more. Strayed was not present when her mother died; no one was with her in the hospital room. For years, she says, the absence left her feeling as if most of her insides had frozen. She repeatedly reviewed the choices that kept her from being there, but thinking through them only deepened her distress. The memory gives the column’s advice about grief its particular authority without suggesting that reflection can undo what happened.

That approach shapes Sugar’s answer to Living Dead Dad, whose son was killed when a driver ran a red light. The letter asks how a bereaved father can go on and become human again, and acknowledges the writer’s fear that Sugar might not answer because she had not lost a child. Sugar does not claim to know what it is to lose a son. Instead, she says that the father’s letter already shows his humanity and directs attention to the love that remains beneath rage, suicidal thoughts, and regret. Drawing on her own continuing love for her mother, she presents grief not as proof that the death was deserved or meaningful, but as evidence of the bond that survives it. The consolation she offers is modest: recognizing such enduring love cannot prevent suffering, but may help someone survive the next day.

Her replies also expose the gap between a polished account of love and the body’s less orderly response. In one recollection, a woman from a city thousands of miles away calls the home Strayed shares with Mr. Sugar and asks for him. He is absent. Strayed knows the woman’s name from a postcard and has previously been told that she and Mr. Sugar are acquaintances. Their relationship seems secure to Strayed and to the people around them; she understands them as an exceptionally happy couple. Yet holding the phone, she feels her heart race and asks the caller whether she knows who she is. The scene does not, in the supplied account, settle what the call means. Its force lies in the discrepancy between the reassuring story of perfect certainty and the unease that surfaces inside it.

Love, Family, and the Everyday

Sugar’s perspective is not limited to solemn confessions. Writing as a mother, Strayed remembers her children’s fierce dispute over the detached head of a black-haired plastic princess. The tiny head, about the size of a gumball, could be snapped onto either of two toy bodies: an ancient Egyptian figure held by her daughter or a skirted pirate held by her son. Neither children’s turn-taking nor the crowded roomful of alternative toys could end the quarrel. The episode makes family life vivid through a small, absurdly absolute conflict, rather than treating motherhood as a string of solemn lessons.

In a separate answer to a woman worried about being fat, Sugar rejects the premise that a round stomach is a worthwhile measure of a person’s value. Her reply urges the correspondent to feed herself and to expect love from people who will not make her body a condition of affection. She follows that advice with a startling story about a close female friend who, in the middle of their twenties, crawled naked into her bed and warned her to run away. The example turns a question about dating into a warning to take another person’s words and behavior seriously, even when desire or closeness might make them easy to dismiss.

Narrative Role and Significance

Sugar is not a conventional character moving through one continuous plot. She is a recurring speaking identity whose story emerges across separate letters: a correspondent arrives with a carefully framed problem, and Sugar replies by testing that framing against consequences, remembered experience, and sometimes an uncomfortable truth. The collection’s form keeps strangers’ accounts distinct, while Strayed’s personal memories create points of contact between their lives and hers. Her own story is not offered as a universal solution; it is evidence she brings into an exchange that remains specific to the person who wrote.

The change from Almond’s invented persona to Strayed’s public voice also sharpens the distinction between a character and the person writing under that name. Almond found that wit could stand in for feeling; Strayed’s answers repeatedly make feeling, including painful and unresolved memory, part of the work. Sugar’s authority consequently rests not on claiming perfect knowledge but on naming what she can know, admitting what she cannot, and still answering. The result is an advice-column character defined less by a fixed biography than by a practice: confronting the stories people tell about love and loss, and asking what becomes possible when they look at those stories honestly.