Research has suggested that both age and personality play a role in emotional experience and regulation, but these variables have not been considered together to determine the relative contribution of each. This study simultaneously examined age and agreeableness differences in the experience of sad stimuli. Participants were 46 younger adults (age, M = 22.04 years, SD = 5.41 years) and 48 older adults (age, M = 74.23, SD = 7.82 years). Participants were asked to predict how sad stimuli (i.e., sad photos) would make them feel and were then measured on their actual reaction to the stimuli (reactivity) as well as on their emotional recovery. Agreeableness, but not age, was related to predicted levels of sadness, such that the more agreeable, the higher the predicted sadness ( = 0.37). In contrast to expectations, prediction accuracy was not related to age or agreeableness. For emotional reactivity, agreeableness ( = 0.16), but not age, was related to reactivity to sad stimuli (i.e., more agreeable, higher reactivity). Finally, age ( = 0.14) was significantly related to emotional recovery such that the older adults reported lower levels of sadness at posttest than did the younger adults. Similarly, people who were more agreeable also reported better emotional recovery ( = 0.15). These relationships were not affected by depression or pretest sadness ratings. Overall, these findings suggest distinct roles for age and agreeableness in predicting different components of the emotion regulation process. An individual with advanced age, high levels of agreeableness, or both may be well-positioned for resilience throughout the emotion regulation process.