Prior studies on older adults' risk taking have paid little attention to the healthcare domain or social influences on decision making. This study examined age-related differences in medication risk taking and the effects of a collaborative decision-making experience on individuals' tendency to take risks. We recruited 24 younger (mean age = 19.50, SD = 1.41) and 24 older adults (mean age = 70.54, SD = 2.30), and asked them to choose between hypothetical medications that differed in probabilities and outcomes of treatment success. To investigate the effects of risk-neutral versus risk-advantageous trials, participants chose between a risky option and a sure option that had equal expected values (risk-neutral) or between a risky option and a sure option that had a lower expected value (risk-advantageous). Participants completed the decision task first individually (the pre-collaboration phase), then in dyads (the collaboration phase), and once again individually (the post-collaboration phase). During the pre-collaboration phase older adults showed a smaller increase in risk-taking tendency in response to risk-advantageous trials compared to younger adults. The pre-and post-collaboration data showed that older adults' risk preferences converged towards their partner's preference to a greater extent following collaboration relative to younger adults. These findings highlight the importance of designing decision aids to encourage older adults to take risks when risk taking is beneficial, and considering how social processes influence patients' medication decisions.