In today’s encounters with vehicles, pedestrians are often dependent on cues in drivers’ behavior such as eye contact, postures, and gestures. With an increased level of automation, and the transfer of control from the driver to the vehicle, the pedestrians cannot rely on such cues anymore. The question is: will there be new communication needs to warrant safe interactions with automated vehicles? This question is addressed by exploring pedestrians’ willingness to cross the street and their emotional state in encounters with a seemingly automated vehicle. The results show that pedestrians’ willingness to cross the street decrease with an inattentive driver. Eye contact with the driver on the other hand leads to calm interaction between vehicle and pedestrian. In conclusion, to sustain perceived safety when eye contact is discarded due to vehicle automation, it could be beneficial to provide pedestrians with the corresponding information in some other way (e.g., by means of an external vehicle interface).