Communication between road users is a major key to coordinate movement and increase roadway safety. The aim of this work was to grasp how pedestrians (Experiment A), cyclists (Experiment B), and kick scooter users (Experiment C) sought to visually communicate with drivengers when they would face autonomous vehicles (AVs). In each experiment, participants (n = 462, n = 279, and n = 202, respectively) were asked to imagine themselves in described situations of encounters between a specific type of vulnerable road user (e.g., pedestrian) and a human driver in an approaching car. The human driver state and the communicative means of the approaching car through an external Human-Machine Interface (eHMI) were manipulated between the scenarios. The participants were prompted to rate from “never” to “always” (6-point Likert scale) the frequency with which they would seek eye contact with the human driver either in order to express their willingness to cross or to make their effective decision to cross. Our findings revealed that a passive human driver in an AV with no visual checking on the road triggered a decline in vulnerable road users’ desire to communicate by eye contact (Experiments A–C). Moreover, the results of Experiment C demonstrated that the speed screen, the text message screen, and the vibrating mobile app eHMI signals diminished kick scooter users’ desire to communicate visually with the human driver, with some age-based differences. This suggested a better comprehension of the approaching car’s intentions by the kick scooter users, driven by the features of the eHMI.