Within a communication predicament of aging framework, this study examined assertiveness as an option for older adults confronted with a problematic health care conversation. Older and younger participants evaluated scenarios in which senior client targets with or without hearing loss employed either assertive, passive, or aggressive responses. As predicted, assertive seniors were evaluated as most competent and likely to be satisfied with future encounters. Compared to older adults, young adults gave equivalent ratings for assertiveness but viewed the senior’s passive response especially positively and the aggressive response especially negatively. Hearing loss made no difference in evaluations of the three response styles. Findings are discussed in terms of the benefits for older adults of developing skills in selective assertiveness, with emphasis on their successful management of health care encounters.