Woolson was the grandniece of novelist James Fenimore Cooper and, when her father died in 1869, the few remaining members of the family moved to Florida. There, she began writing, publishing short works in major publications like The Atlantic Monthly. After her mother's death in 1879, she traveled more widely, particularly in Europe and especially Italy. Woolson's most famous work is likely "Miss Grief" (1880), which is set in Rome.
The protagonist, a young male writer, is told that a woman came to see him and left only the name "Miss Grief." Grief, admits the narrator, has not visited him during his carefree time in Europe and he intends to keep it that way. Though she continuously came calling, he made sure to be elsewhere, until her eighth visit. "Not Grief," she says; her name is "Miss Crief" (though he continuously refers to her incorrectly) and she admits that she has read all his writings and even committed some to memory:
...Without pause, she began to repeat something of mine word for word, just as I had written it. On she went, and I — listened. I intended interrupting her after a moment, but I did not, because she was reciting so well, and also because I felt a desire gaining upon me to see what she would make of a certain conversation which I knew was coming — a conversation between two of my characters which was, to say the least, sphinx-like, and somewhat incandescent as well. What won me a little, too, was the fact that the scene she was reciting (it was hardly more than that, though called a story) was secretly my favorite among all the sketches from my pen which a gracious public has received with favor. I never said so, but it was... She had understood me — understood me almost better than I had understood myself. It seemed to me that while I had labored to interpret, partially, a psychological riddle, she, coming after, had comprehended its bearings better than I had, though confining herself strictly to my own words and emphasis. The scene ended (and it ended rather suddenly)...
Miss Grief has come with a manuscript, hoping the young author will help her have it published. To his surprise, he enjoys it and asks for other examples of her writing. But, when he suggests she make a few edits, she refuses and, she admits, if he reveals he does not like her work, she will be destroyed. On her deathbed, she asks for her manuscripts to be destroyed. Woolson herself was deeply affected by the deaths in her own family. Decades later, in her 50s, she took her own life.