| Quote #4
It was strange that neither when it was over nor a long time afterward did he regret that night. Looking at it from the perspective of ten years, the fact that Judy's flare for him endured just one month seemed of little importance. Nor did it matter that by his yielding he subjected himself to a deeper agony in the end and gave serious hurt to Irene Scheerer and to Irene's parents, who had befriended him. There was nothing sufficiently pictorial about Irene's grief to stamp itself on his mind. (5.1)
Although Dexter's memories of this time when he broke off his engagement with Irene Scheerer do eventually cause him agony (much-deserved agony, we should add), he can't seem to regard them as anything but facts of life. Dexter loves Judy, Judy ditches Dexter – that's just the way things go. The past appears to be a fixed point for Dexter, something that you can feel bad about, but not something that you can change or regret.
| Quote #5
"So you're from the Middle West," said the man Devlin with careless curiosity. "That's funny – I thought men like you were probably born and raised on Wall Street. You know – wife of one of my best friends in Detroit came from your city. I was an usher at the wedding." (6.3)
By the end of the story, Dexter is so successful that his colleagues all associate him entirely with Wall Street and financial success. They can't even imagine him in relation to another, less wealthy place. Dexter's current wealth has erased his past in the Midwest. In "Winter Dreams," success has a geographical component: being a real captain of industry means living in New York. The cities of Minnesota have wealthy people in them, but if you're really going to make it, you have to do it on Wall Street. Do you think this has changed since the 1920s?
| Quote #6
"Look here," said Dexter, sitting down suddenly, "I don't understand. You say she was a 'pretty girl' and now you say she's 'all right.' I don't understand what you mean – Judy Jones wasn't a pretty girl, at all. She was a great beauty. Why, I knew her, I knew her. She was – "
We've seen throughout the whole story that Dexter's love for Judy is like an ideal. Her beauty is so bewitching that, no matter what she does, he can't seem to stop loving her. Here, we get a startling outsider perspective: that enchanting quality about Judy seems to have disappeared. She has aged, and clearly hasn't had any Botox. Judy's loss of her beauty is like the final disillusionment for Dexter. One final nail in the coffin of his winter dreams.