It is commonly assumed in affluent, Western, democratic societies that by enhancing opportunities for choice, we enhance freedom and well-being, both by enabling people to get exactly what they want and by enabling people to express their identities. In this paper, we review evidence that the relationships between choice, freedom, and well-being are complex. The value of choice in itself may depend on culture, and even in cultural contexts that value choice, too much choice can lead to paralysis, bad decisions, and dissatisfaction with even good decisions. Policy-makers are often in a position to enhance well-being by limiting choice. We suggest five questions that policy-makers should be asking themselves when they consider promulgating policies that will limit choice in the service of enhanced well-being. The relationships between choice, freedom, and well-being are not simple, and an appreciation of their complexity may help policy-makers target their interventions more effectively.