In Pineapple Street, Jackson explores the various consequences of seeking happiness through wealth alone. Despite the immense wealth of the Stockton family, their members still face many internal and external conflicts that are not solved by money and are in fact sometimes caused by it. One of the things that Sasha, Georgiana, and Darley have in common is their various realizations of how profoundly money can complicate one’s pursuit of happiness.

At first, Darley appears to be a character who chooses to value her relationship with her husband over her family’s money. She gives up her rights to her inheritance so that Malcolm doesn’t have to sign the Stockton pre-nuptial agreement, even though he is perfectly willing to do so. This demonstrates that Darley doesn’t see money as the key to happiness and instead chooses love as the source of her happiness. Yet Darley does still value money a bit too much. When she let go of her inheritance, she and Malcolm were both making high salaries, and Darley’s lifestyle didn’t change at all. When Darley gave up her job to be a stay-at-home parent, she relied on Malcolm’s income to uphold their luxurious lifestyle. But when Malcolm is fired from his job, Darley is forced to revisit her relationship with money.