Empathy—which typically instigates prosocial behavior—comprises both cognitive and affective facets. Research suggests that the cognitive facet of empathy (empathic accuracy) declines with age, whereas the affective facets of empathy (emotional congruence and sympathy) remain stable or increase with age. Going beyond main effects of age, we tested whether working in occupations with varying emotional job demands (EJDs) moderates the effects of age on empathy. We predicted that emotionally demanding occupations provide opportunities to practice empathy and, as a result, may lessen the negative relationship between age and empathic accuracy and/or strengthen the (positive) relationship between age and the affective facets of empathy. A sample of 128 employees (19–65 years) who differed in self-reported EJDs was recruited. Participants viewed film clips portraying different persons retelling a work event during which they experienced positive or negative emotions. After each clip, participants rated the intensity of the protagonist’s and their own emotions. Consistent with prior research, our analyses revealed a negative association between age and empathic accuracy, while there were no age differences in emotional congruence and a positive association between age and sympathy. Only the relationship between age and emotional congruence was moderated by EJDs. Contrary to our prediction, relatively older employees in emotionally demanding jobs experienced lower emotional congruence than younger employees. This may suggest that people learn about the double-edged nature of sharing other’s feelings as they progress in their career, and thus, keep a healthy distance. Implications for age-comparative research on prosocial processes across adulthood are discussed.