What comforting thoughts could be relayed to Dexter during his crisis at the end of "Winter Dreams"?

A comforting thought that can be given to Dexter is for him to not be afraid to look life in the face, and to see it for what it is.  His obsession with "Winter Dreams" convinced him that the ideal is what life should be and how life should be viewed.  I think that being able to see life for what it is at the end of the story might be the start of something more real and substantial in his life.  The premise of his "Winter Dreams" is love of an ideal that is shallow and not substantive.  I think that a comforting notion that might be given would be that while "that thing is gone," in its place something more real and valid can arise.

Another thought of comfort that can be relayed to Dexter would be for him to take stock of how his life has changed and that there is an upward trajectory to it.  The ending is one in which there is an embrace of the tragic condition. He stares out at the New York skyline "into which the sun was sinking in dull lovely shades of pink and gold."  It is a scene that lends itself to being tragic and Dexter ends up wallowing in it with the ending.  However, the reality is that something inside Dexter compelled him to leave Judy.  Something inside him understood that his ability to fully accomplish his "Winter Dreams" was never going to happen.  Something to comfort Dexter would be that while there is sadness about his dream being gone, it might never have been there for him in the first place.  His initial desire to leave and live a life apart from Judy is a step towards his own independence, an embrace of his own autonomy.  While there is loss at his discovery of Judy, there can be an advising for Dexter to shed the tragic condition and understand there is also a sense of reality about who he is and how he shall live.   This cannot be that bad of a thing.

What comforting idea could you offer Dexter in "Winter Dreams" by F. Scott Fitzgerald?

F. Scott Fitzgerald's masterful "Winter Dreams," frequently discussed as a first draft of The Great Gatsby, looks at the themes of attaining dreams and pursuing hopeless ventures. To explore these themes and others, Fitzgerald presents readers with Dexter, a young man of ambition who lacks the clarity to find fulfillment in his dreams.

In the story, Dexter becomes disillusioned as he is “unconsciously dictated to by his winter dreams” (p. 2). These dreams are of both a love interest and material gain. Over time, Dexter goes from knowing what he wants to “[surrendering] a part of himself to the most…unprincipled personality" (p. 5).

If one believes that Dexter's problems stem from a lack of clarity on the value his dreams, one piece of advice to comfort Dexter may be to prioritize his pursuits. The story leads us to believe that dreams without purpose are destined to fail; Fitzgerald ends the story noting that "even the grief [Dexter] could have borne was left behind in the country of illusion," signaling Dexter's dreams as unattainable (p. 9). Dreams and goals therefore must mean something to an individual for one to find fulfillment in making their dreams reality.