In the painting, DeKay is seated on a couch in profile, dressed in black and looking down at a closed book in her hands. The indoor setting, presumably Homer's studio, is dark and empty but for a small spot of color on the floor–a discarded and dying rose; a few of its petals scattered nearby.
It is "a very suggestive picture, and unlike any other he painted," says Nicolai Cikovsky Jr., a Homer biographer and retired National Gallery of Art curator. "I'd say she is the most nameable candidate (for a love interest), certainly."
A letter from Homer to De Kay in December 1872 indicates that something had come between them. He asks her to pick up a sketch he had made of her, adding a few cryptic words of reassurance: "I am very jolly, no more long faces. It is not all wrong."
The next year, another of Homer's notes alludes to his feelings by what it omits: "My dear Miss Helena, I have just found your picture. I think it very fine. As a picture I mean, not because, etc."
It is unclear whether Homer ever actually proposed to De Kay, but he painted a picture of a proposal scene in 1872, with the telling title, "Waiting For an Answer," and in 1874 he painted an almost identical scene minus the young suitor ("Girl in an Orchard"), suggesting that the girl's answer had been to send the boy away. Around the same time, he painted several other pictures of "thwarted love," as Burns describes it.
Some scholars think he fell in love again a few years later, when he was around 40 years old. He visited friends in rural Orange County, New York, and painted several pictures of women there. One of them, titled "Shall I Tell Your Fortune?" shows a saucy-looking lass seated barefoot on the grass, holding playing cards in one hand. Her other hand rests palm-up on her hip, and her direct gaze seems to be asking the painter much more than the title suggests.
A similar woman appears in other Homer paintings from the mid to late 1870s, and this may have been the schoolteacher referred to by Homer's grandniece, Lois Homer Graham, in a piece she wrote for the book Prout's Neck Observed decades later: "The year 1874 found all of the Homer sons well established in their careers…Winslow had courted a pretty school teacher, but lost her to his career."
It does seem clear that Homer wanted a major change of scenery and lifestyle rather suddenly at the end of the 1870s. As Cikovsky puts it, "something was stirring in Homer's life, and I think some sort of intimacy gone wrong was part of that."
The artist withdrew from society, moving first to an island off Gloucester, Mass., then the remote fishing village of Cullercoats, England, and finally in 1883 to Prout's Neck, Maine, where he stayed the rest of his life. He developed a reputation as a grumpy recluse, discouraging visitors and turning down most social invitations, although he remained close to his family. His personal life may have suffered, but his professional life flourished in these years, as the seacoast inspired some of his best works.
Interestingly, Homer never attempted to sell the painting of the fortune-telling girl. It was still on an easel in his Prout's Neck studio when he died in 1910.