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I assume that you are asking how this story proves this quote.
In the story, Jim and Della do not upset their most cherished plans through their own actions. What they do is very similar, though. They upset each other's most cherished plans.
In the story, each member of the young couple wants to do something very nice for the other. So they both sell off their most treasured possessions in order to be able to do that.
But they upset each other's plans. They both buy something that was meant to complement the possession that the other sold.
In O. Henry's story, "The Gift of the Magi," Della bemoans the fact that she has only one dollar and eighty-seven cents with which to purchase a Christmas present for her beloved husband. But, she suddenly has the idea that if she sells her hair, she will have enough money with which to buy the a watch chain for her Jim. This is her cherished plan, one that she holds dear since it is the only way that she can procure enough money for the watch fob.
So, she goes to Madame Sofronie's and sells her hair; takes the twenty dollars and buys Jim a beautiful watch chain. However, as fate would have it, Jim has sold his watch because he, too, had not enought money with which to buy his beloved Della the lovely hair combs he had seen in a shop. Indeed, through the actions of Della and Jim fate "upsets their cherished plans" of delighting one another with lovely gifts. Yet, of course, they received greater gifts, the affirmation of one another's unselfish love.
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