Dexter has already been in love with the beautiful and mercurial Judy Jones when he dates Irene Scheerer. He is very close to becoming engaged to Irene—not because he truly loves her, but because he could have a safe and solid marriage to her and become part of her more cultured and elite world. However, when Judy Jones, whom he has always loved in a fitful way, returns, he throws over Irene and decides not to marry her.
In the end, he and Judy date again for only a month before Judy leaves him. He would like to marry her, but she is not interested in marrying him. He knows that he will love her forever, but she marries another man who is cruel to her. Dexter does not marry anyone, and he is upset about his childhood dreams and misconceptions when he gets older.
Perhaps the simplest answer to the question is this: Dexter did not know how to love either of them. Throughout the story, it seems that Dexter is as much in love with the idea of what constitutes romantic love as he is with the belief that to love someone is to possess them. By doing both of the aforementioned, Dexter is never able to see either Judy or Irene as a fully-fledged human being. Dexter idolizes Judy to the point of objectification: she is one of the “glittering things” he longs to possess. Although he believes that he loves her, he realizes that she is beyond his grasp. In desperation, he turns to Irene and in doing so, objectifies her, too. One could think of the poorer and plainer, but more steadfast Irene as his runner-up or rebound relationship choice. In fact, one of Dexter’s reasons for pursuing Irene was to make Judy jealous. Acting on his obsession with Judy not only shattered any hope of happiness he might have had with Irene but also completely alienated him from her, as well as her family.
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