A joke is amusing if and only if it’s fitting to be amused by it; an act is regrettable if and only if it’s fitting to regret it. Many philosophers accept these biconditionals and hold that analogous ones obtain between a wide range of additional evaluative properties and the fittingness of corresponding responses. Call these the _fit–value biconditionals_. The biconditionals give us a systematic way of recognizing the role of fit in our ethical practices; they also serve as the bedrock (...) of various metaethical projects, such as fitting-attitude analysis of value and the ‘fittingness first’ approach. Yet despite the importance of the biconditionals, there is very little discussion of their proper interpretation. This paper argues that any plausible interpretation of the fit_–_value biconditionals must disarm several kinds of apparent counterexample. For instance, that an achievement is pride-worthy doesn’t imply it is fitting for me to take pride in it because the achievement might not be mine or that of anyone close to me; that a joke is amusing doesn’t imply it is fitting for me to be amused by it for six straight months; and that a person is loveable doesn’t imply it is fitting for me to love him romantically because that person might be my sibling. We consider possible responses to such counterexamples and develop what we consider the most promising interpretation of the biconditionals. The upshot is that certain widespread assumptions about fit and its relation to value and reasons should be reconsidered. (shrink)