The mood of “Winter Dreams” is tortured and bleak. While Dexter has moments of feeling joyful—specifically when receiving affection from Judy—these moments are often euphoric in a destabilizing way rather than comforting or nurturing. For the most part, the story is centered on Dexter’s deep desire for what he does not have (wealth, Judy, etc.) and decades of dissatisfaction as he is unable to have everything that he wants at once.
It is only at the very end of the story, when Dexter learns from his friend Devlin that Judy has lost her beauty and resigned herself to an unhappy marriage, that Dexter finally faces the fact that he will never have the perfect life he imagined for himself (as part of his “winter dreams”), as he will never end up with the young and vivacious version of Judy he still longs for. The mood changes in this moment from tortured to resigned, as seen in the following passage:
For the first time in years the tears were streaming down his face. But they were for himself, now. He did not care about mouth and eyes and moving hands. He wanted to care, and he could not care. For he had gone away and he could never go back any more. The gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time. Even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.
The mood shift here is palpable. Rather than avoiding his feelings via his endless striving, Dexter starts to cry “for the first time in years” and reflects on how “the gates [are] closed” and “the sun [has] gone down.” In this way, readers are given the opportunity to grieve alongside Dexter for all that he has lost while living in “the country of illusion […] where his winter dreams had flourished.” Though this is far from a “happy ending,” Fitzgerald’s language here implies that, in his grief, Dexter experiences a kind of freedom via letting go of his “winter dreams” and resigning himself to the life he has in front of him.
