Analyzing the Text
Dexter’s family, while not the richest in the area, is still fairly well-to-do.
Dexter dreams of a better and more exciting life among the rich. This choice on the part of Fitzgerald foreshadows what will happen in Dexter’s adult life.
He is shocked by how much he is attracted to the young Judy and wants to be her equal, rather than serving her.
His winter dreams are about beauty, success, and wealth. They shape Dexter’s decision to pursue Judy and eventually move to the East Coast.
She is used to getting her way through beauty and charm and has a bunch of male admirers/suitors. Although she is beautiful on the outside, internally she is troubled.
He probably suspected as much. The clues can be found on lines 660-664, when he feels a mixture of emotions including anger and hatred at his complicated relationship with Judy.
He laughs when with Devlin, but as soon as the other man leaves he begins to weep. “There was something in me, but now that thing is gone” means that he could cling to the image of Judy’s beauty but now that it no longer exists, it is only a memory. That era of his life is gone.
He is motivated to succeed by the promise of money and the possibility of a future with a beautiful woman such as Judy. He deserves some sympathy, since Judy broke his heart numerous times, but also merits criticism since it would seem that he doesn’t care about her personality but only her beauty. He loved her, but it was a shallow love.
He has lost the reason for his motivation to succeed. Ever since he was a young boy and saw Judy for the first time, he wanted to be part of that beautiful and wealthy life. He worked hard to succeed and make a lot of money, which allowed him to socialize with a higher class than the one he was born into. Now that her beauty is no more, though, his primary motivation to reach and maintain that way of life is gone.