Background/Objectives: Life expectancies have increased in most countries, leading to a higher accident rate among older drivers than their younger counterparts. While numerous studies have analyzed the decline in cognitive abilities and physical limitations as contributing factors, there are other considerations. For instance, younger male drivers tend to take more risks than younger female drivers. However, there is a lack of research and evidence regarding the role of gender in risk-taking among individuals over 65. Given this gap, our current study aims to investigate the relationship between gender and risk propensity in this particular age group. The primary goal was to determine if driving experience affects the gender gap in risk attitude; Methods: We studied risk behavior in both car drivers and pedestrians. Our sample included 200 individuals (101 women), all over 65, with the same weekly driving times. After a brief demographic and anamnestic interview, they completed the Driver Road Risk Perception Scale (DRPS) and the Pedestrian Behavior Appropriateness Perception Scale (PBAS) questionnaires. They also provided information about traffic violations and road crashes; Results: Our research revealed that older male drivers continue to tend to risky behavior, highlighting the need for targeted interventions to improve risk awareness, especially among older men; Conclusions: Our findings suggest that road safety messages should specifically target male drivers as they are less likely to view responsible driving actions, such as observing speed limits, as desirable.