Another irony about Dexter thinking of Judy as his own is that he may have suspected he would never win her love. He says one thing but knows that the truth is diametrically opposed to the words he speaks with such conviction.
Dexter was at bottom hard-minded . . . He was completely indifferent to popular opinion. Nor, when he had seen that it was no use, that he did not possess in himself the power to move fundamentally or to hold Judy Jones, did he bear any malice toward her. He loved her, and he would love her until the day he was too old for loving—but he could not have her. So he tasted the deep pain that is reserved only for the strong, just as he had tasted for a little while the deep happiness.
Dexter understands the challenges involved in winning Judy's love. He may even...
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have suspected that his efforts would eventually prove futile. However, because he is "hard-minded" and "strong," he willingly risks emotional annihilation. He pursues the elusive Judy against his best judgment. The words "hard-minded" and "strong" refer to Dexter's capacity for risk-taking. Because of his resilience, he bears Judy no malice when she rejects him. Dexter understands the risk of loving Judy but is willing to bear the price, in order to experience "for a little while the deep happiness" of an exquisite romance.
So, the irony of Dexter thinking of Judy as his own is that he knows the opposite is true. However, he is willing to suspend reality in order to experience an acute, temporal pleasure.
It is interesting to see Dexter believing Judy as "his own" because it reflects Fitzgerald's assertion that some dreams are powerful enough to control the beholder as opposed to the individual controlling it. What this ends up meaning is that Dexter truly believes that he controls his ability to dream and revere Judy and what she represents to him. In reality, he is being controlled by the pursuit of an exterior end that has little, if anything, to do with him. He is trapped by the allure of wealth, privilege, and established money and seeks to enter this world. In this process of coveting, the reader understands that Dexter is not in control of it, as it is in control of him.
Dexter’s thinking of Judy as “his own” is completely ironic because throughout most of the story, she has no real regard for him. When they first meet as children, Judy simply wants Dexter to be her caddy and continues to call him “Boy” even though he is clearly older than she is. Judy never even bothers to ask Dexter his name. When they meet again later in life, Judy uses Dexter and his attentions for selfish motives. He is quite smitten by her, but Judy treats Dexter with wavering indifference. Judy is a reckless character, one who could never really “belong” to anyone but herself.