Although considerable evidence indicates that dispositional empathy is associated with the degree of help that observers will offer needy targets, little is known about the effect of empathy on one’s initial willingness to enter situations in which such needy targets might be found. Three studies were conducted to evaluate two related propositions: (1) that dispositional empathy influences such situational preferences, and (2) that this influence is mediated by the expectancies one holds regarding the emotions likely to occur in those situations. Using hypothetical judgments, Study 1 found support for both propositions. Study 2, in which participants believed that their responses actually committed them to encountering needy targets, provided further support for the model, as did Study 3, which examined the experiences of actual community volunteers. The theoretical and practical implications of these findings are discussed.