Stephen Elliott

Stephen Elliott is the writer whose idea for The Rumpus gave rise to Dear Sugar, first as his own advice column and later as a role he offered to Cheryl Strayed. His brief tenure established the column’s irreverent ambition, but his recognition that he was performing empathy rather than consistently reaching it helped make way for the more searching voice that followed.

Writer and Founder of The Rumpus

Elliott imagined The Rumpus as an online community organized around literature. As a writer without much money, he asked writer friends in similarly impoverished circumstances to help build it. They agreed partly out of affection for him and, as Strayed’s account puts it, because they wanted a distraction that seemed noble. The project thus began not as a solitary undertaking but as a collaboration among writers drawn together by friendship and a shared literary purpose.

Creating Dear Sugar

Elliott’s contribution to the site was an advice column. He proposed the name Dear Sugar Butt, borrowed from an endearment he and Strayed had used in their email correspondence; the name was mercifully shortened to Dear Sugar. He regarded taking on an advice-columnist’s job as an arrogant move, but justified it by wanting to create something different: irreverent and brutally honest rather than conventionally soothing.

That ambition depended on a persona. Elliott conceived Sugar as a woman with a troubled past and a slightly reckless tongue. Sometimes the character felt real to him, and he felt able to enter into his correspondents’ pain. More often, however, he relied on wit when he could not reach them emotionally. After a year of writing columns, he quit. The limitation he describes was not a lack of cleverness but the gap between the persona’s apparent intimacy and his own intermittent ability to connect with the people writing for help.

Passing the Column to Cheryl Strayed

Around the time he left the column, Elliott read a nonfiction essay by Strayed, whom he already knew as the author of the novel Torch. Its searing recollection of infidelity and mourning gave him what he describes as a tingling hunch: he wrote to ask whether she would take over as Sugar. The proposal was strikingly impractical. Strayed had two small children, substantial debt, and no regular academic position, and the online column offered no pay. Elliott nevertheless made the request, relying in part on an unusually personal connection: she had written the only fan letter he had received as Sugar.

Role in Sugar’s Emergence

Elliott’s part in the column’s history is both creative and transitional. He supplied the literary community, the advice-column format, and the name, but his own account also marks the point at which those elements proved insufficient without a more felt engagement with correspondents’ pain. By inviting Strayed to succeed him, he set the conditions for Sugar’s transformation from a deliberately fashioned persona into a voice capable of making an unprecedented disclosure. His story therefore frames the column’s emergence as a handoff: an initial experiment in candor and wit gives way to a form of advice grounded in personal testimony.