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Adam Smith famously presents readers with two portraits of human motivation and morality: the self-interest depicted in The Wealth of Nations, and the other-regarding sympathy central to The Theory of Moral Sentiments. Known as the “Adam Smith Problem,” the question of how to reconcile these two depictions has generated much scholarship, with no clear consensus emerging. This paper uses Alexis de Tocqueville’s Democracy in America to interrogate the fate of the “Adam Smith Problem” in an age of democracy. One the one hand, Tocqueville’s portrait of the relations between male family members suggests that the equality undergirding democratic society removes interest-based barriers to the “natural feelings,” thus opening possibilities for the expansion of sympathy and greater inclusiveness within democratic society. On the other hand, Tocqueville’s discussions of white settlers’ interactions with Native Americans point to the limits of sympathy’s extension, to the intractability of self-interest, and to potentially intractable barriers to democratic inclusiveness.