Fitzgerald's short story "Winter Dreams" has two conflicts in its narrative arc, a societal rich versus poor external conflict very similar to that experienced by Gatsby, and a more central internal conflict raging in its protagonist Dexter Green, whose winter dreams, coffin-like, close up on him "like the white lid of a box."
Old Rich vs. New Rich
"Winter" might be a warm-up for "Great Gatsby," since it follows the external conflict of the "establishment" versus the "nouveau riche" as firmly as Fitzgerald's novel, published three years later. Dexter and his lover, Judy Jones, keep missing each other romantically; once he becomes rich enough to socialize with her, he finds her kisses "like charity . . . she was entertained only by the gratification of her own desires." Dexter, meanwhile, feels there is nothing to "cure his illusion as to her desirability," a direct correlative to the animalism versus refinement conflict that fascinated Fitzgerald.
Dexter's Internal Conflict
The short story parts company with Gatsby's novel when "Winter Dreams" examines the internal conflicts shared by both Dexter and Judy; as a narrative the tale has far more in common with Dickens' "Great Expectations," where love-sick Pip becomes a gentleman for the cold Estella. Like Dickens' characters, the lovers in "Winter Dreams" are uncomfortable in their own skin; Dexter feels "like an intruder" even in social settings where he has earned his place. When it comes to consummating his love for Judy, he suddenly feels "that he had never loved her."
Judy's Internal Conflict
Ironically, Judy herself feels the same dissociation and lack of self-identity. After a narrative full of selfish caprices, she suddenly confesses "brokenly" to Dexter, "'I'm more beautiful than anybody else . . . why can't I be happy?'" In Judy's mind as in Dexter's, their reach exceeds their grasp; the mental conflict of appearance versus reality poisons their lives. In the end, like Dickens' Estella, Judy marries an abusive man and fades into plainness; Dexter cries when he hears about this, but "his tears were only for himself . . . he had gone away and could never go back."
Conflicts Mirror Each Other
The most fascinating point about this short story is that its internal conflict mirrors its external one, reversing it. Judy and Dexter, old versus new rich, are equally unhappy, uncomfortable and self-deluded. Fitzgerald describes both as being confident to an enormous degree, but their external confidence is in exact proportion to their internal lack of self-identity, which robs them of emotional affect. They "wanted to care and . . . could not care." Fitzgerald pronounces these words, epitaph-like, at the tale's end, set in wintry gray.