This study quantifies bidirectional gazing—when drivers and pedestrians look at one another—in a naturalistic setting. Understanding bidirectional gazing provides insights into the communication dynamics between pedestrians and drivers, and their relation to infrastructural support (e.g., a stop sign). Findings demonstrate that 36% of observed road crossings included at least one bidirectional glance. There was a tendency for bidirectional gazing to be more prevalent (especially early in encounters) and longer for crossing types with less infrastructural support, such as undesignated crossings. This suggests that when pedestrians lack infrastructural support and are farther away from the lane, drivers and pedestrians rely more on visual communication (looking at each other) to determine things like gap size, trajectory, speed, and distance. However, when pedestrians are closer to the lane, we find similar gaze patterns across the crossing types, which may suggest another gaze-behavior type (e.g., checking if it is safe to cross).