At one point, Judy acknowledges the void in her life when she admits, “I'm more beautiful than anybody else … why can't I be happy?” Her and Dexter's struggle to achieve happiness underscores Fitzgerald's main critique of the American dream. Fundamentally, the dream is a deceptive world of glitz and glamour that ultimately lacks true substance. While Dexter might have found fulfillment in a genuine relationship with Judy, she lacks the inner strength to fully commit to him.

By the end of “Winter Dreams,” Dexter has accepted the failure of his relationship with Judy, yet he still clings to the enchanting dream of her and her world. However, when a business associate tells him that she has lost her youthful beauty and has become a passive wife to an alcoholic and abusive husband, his fantasies shatter. He then realizes, “the gates were closed, the sun was gone down, and there was no beauty but the gray beauty of steel that withstands all time.” In the end, he mourns not for Judy, but for the lost golden world, “the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.”