Why is Devlin surprised that Judy ends up with his best friend in "Winter Dreams"?
To a great extent, Devlin is suprised at Judy's predicament because he feels that she could have done better. He is not as surprised as Dexter, who is mortified at the image of Judy presented, but Devlin reflects a sesne of slight surprise at how Judy's life changed from the time she married to now:
One day, a man named Devlin comes to see him about business and tells him that his best friend is married to Judy. Devlin admits that her husband ‘treats her like the devil’ while she stays home and takes care of their children. He also reveals that ‘she was a pretty girl when she first came to Detroit,’ but that ‘lots of women fade just like that.’’
Devlin has no idea of what Judy used to be like and what she means to Dexter. However, his surprise comes at the fact that Judy's life in Detroit has withered her from what she was to what she is right now. Devlin knows that his best friend is debaucherous and does terrible things, which is why he cannot seem to understand why a girl like Judy would be involved with someone like him. Perhaps, this is why Devlin says that such a fate befalls upon many young women. In the end, Devlin's revelation hints at what he might perceive about Judy, something that has to be confirmed with Dexter's intense reaction to what Devlin says.