Cheryl Strayed and Stephen Elliott

Cheryl Strayed and Stephen Elliott’s relationship joins friendship to creative collaboration: Elliott helped make a space for the advice column Dear Sugar, first inhabited the Sugar persona himself, and later invited Strayed to take it over. Their private email endearment became the column’s original name, but the project’s lasting force came from the way Strayed transformed Elliott’s premise into a practice of frank, personal witness.

Friendship and The Rumpus

Elliott conceived The Rumpus as an online community organized around literature. A writer himself and short of money, he asked equally impoverished writer friends to help build it. Strayed was among the friends in this circle. Their connection therefore preceded the column: it belonged first to a network of writers who cared about Elliott and, as the account puts it, welcomed a distraction that seemed noble.

The advice column began as Strayed’s contribution to Elliott’s project. She proposed the name Dear Sugar Butt, borrowing an endearment that Elliott and Strayed had used in their email correspondence. Its playful, homoerotic quality made it intimate rather than institutional; the name was later shortened to Dear Sugar. The column’s public identity thus carried a trace of the private language between its creator and its first proposed contributor.

Elliott as the First Sugar

The collaboration began with Elliott not only providing a platform but also writing as Sugar. He imagined the columnist as a woman with a troubled past and a somewhat reckless tongue, and wanted the advice to be irreverent and brutally honest. His account distinguishes the persona from his own capacity to inhabit it: sometimes he felt connected to correspondents’ pain, but often he relied on wit when he could not reach their emotional reality.

After a year of writing columns, Elliott quit. The change mattered to the relationship because the column did not disappear with its first writer. Elliott had established the format and the name, but his sense that he was faking the emotional connection left room for another writer to alter what Sugar could be. His later invitation to Strayed was a handoff within a friendship, as well as a decision about the future of the column.

The Invitation

Around the time he encountered Strayed’s nonfiction, Elliott already knew her as the author of the novel Torch. The essay he read was a searing account of infidelity and mourning. It gave him a sense that she might bring to Sugar the emotional directness the persona required, and he wrote to ask whether she would take over.

Elliott recognized the request as unreasonable in practical terms. Strayed had two small children at home, substantial debt, and no regular academic job; the online column would pay nothing. His leverage was not an offer of money or stability but a personal history with the project: Strayed had written the only fan letter he had received while writing as Sugar. That detail makes the invitation reciprocal in an unusual way. The former columnist turned to a friend whose earlier response had already shown that his work had reached her.

A Changed Column and a Shared Legacy

The defining response of Strayed’s tenure answered a letter consisting of a young man’s repeated question, “WTF, WTF, WTF?” Rather than keep the focus safely on the correspondent, she disclosed that her grandfather had sexually abused her when she was three, four, and five. Elliott’s introduction identifies the disclosure as a break with the unspoken conventions of advice writing, which ordinarily keep the columnist’s own experience out of the answer.

The contrast between the two writers’ accounts illuminates the nature of their collaboration without erasing their distinct roles. Elliott created the literary setting, proposed the column, developed its first persona, and recognized in Strayed’s essay a writer who could take it somewhere else. Strayed’s answer made Sugar a phenomenon by refusing the protective distance Elliott had found himself unable to sustain. In his telling, her candor was not simply a startling personal revelation: it announced a mission centered on taking sorrow seriously and asking readers to face the lives they actually have. Their friendship thus became part of the column’s structure—first in the name shared through email, then in Elliott’s invitation, and finally in his introduction of the transformation Strayed brought to Sugar.