Perplexity is an epistemic emotion with deep philosophical significance. In ancient Greek philosophy, it is identified as a catalyst for philosophical progress and personal philosophical transformation. In psychological terms, perplexity is the phenomenological sense of lacking immersion in the world, a state of puzzlement and alienation from one’s everyday surroundings. What could make such an emotion philosophically useful? To answer this question, I examine the role of perplexity in Jane Addams’s political theory and ethics. Addams, a social reformer and American (...) pragmatist philosopher, regarded perplexity as an emotion that arises out of specific situations, such as being part of a social settlement, union actions, or trying to surmount gender expectations. Perplexity allows us cognitive distance from our everyday customary morality and ordinary habits of thinking, and this pushes us to become creative in our philosophical reflection. I contextualize perplexity in Jane Addams’s social reforms, and examine the relevance of her ideas today. (shrink)