In all situations of choice, we face a question that I call "the obvious question'': what shall we do? But sometimes we also face, or should face, a different question, which I call "the tragic question": is any of the alternatives open to us foe from serious moral wrongdoing? Discussing cases of tragic conflict from literature, philosophy, and contemporary life, I argue that it is valuable to face the tragic question where it is pertinent, because facing it helps us think how we might design a society where such unpalatable choices do not confront people, or confront them less often. Cost-benefit analysis helps us answer the obvious question; but it does not help us either pose or answer the tragic question, and it frequently obscures the presence of a tragic situation, by suggesting that the obvious question is the only pertinent question. I apply these reflections to thinking about basic entitlements of citizens, such as might be embodied in constitutional guarantees.