Jane Addams was a social thinker, a public philosopher, and a leader of the settlement house movement in the United States in the late nineteenth and early twentieth centuries. She developed a method to understand people from backgrounds radically different from her own. This approach, which she called “sympathetic understanding,” involved a dialogic process that included “perplexity” and inquiry. This process resulted in practical actions that resonated with people in the neighborhood surrounding Hull House, the settlement house she founded in Chicago. It also transformed Addams's own feeling and thinking. The process is illustrated by the “Devil Baby” tales described in Addams's work. The relationship of her method to empathy with diverse populations and professional empathy in general is discussed.