This small portrait set in an interior is one of only a few by Winslow Homer, whose landscapes and scenes of leisure generally depict anonymous figures. Helena de Kay belonged to the circle of artists and intellectuals that occupied the Tenth Street studios in New York and with whom Homer was associated at the outset of his career. His close friendship with De Kay is expressed in this dark toned composition in which the seated model is shown in profile with her head lowered and holding a book. The composition is similar to Whistlers Composition in Black and Grey No. 1: Portrait of the Artists Mother of 1871. Behind the sitter a rose has fallen on the ground with two of its petals scattered, contributing to the melancholy mood of the painting.
Homer later gave the painting to De Kay on the occasion of her wedding to the publisher Richard Watson Gilder. The inscription at the lower right corner, June 3rd 1874, records the date of the marriage. Several writers have stated that the sitter was the great love of Homers life.