Assessments of interactions between road users are crucial to understanding comfort and safety. However, observers may vary in their perceptions and ratings of road user interactions. The objective of this paper is to examine how perceptions of yielding, comfort, and safety for pedestrian interactions vary among observers, ranging from members of the public to road safety experts. Video clips of pedestrian interactions with motor vehicles and bicycles were collected from 11 crosswalks and shown to three groups of participants (traffic safety experts, an engaged citizen advisory group, and members of the general public) along with questions about yielding, comfort, and risk of injury. Experts had similar views of yielding and comfort to the other two groups, but a consistently lower assessment of injury risk for pedestrians in the study. Respondent socio-demographics did not relate to perceptions of yielding, comfort, or risk, but self-reported travel habits did. Respondents who reported walking more frequently rated pedestrian comfort as lower, and respondents who reported cycling more frequently rated risk as lower for pedestrian interactions with both motor vehicles and bicycles. Findings suggest small groups of engaged citizens can provide useful information about public perspectives on safety that likely diverge from expert assessments of risk, and that sample representation should be assessed in relation to travel habits rather than socio-demographics.