Artificial Intelligence (AI) is poised to reshape the future of mobility with autonomous vehicles tackling the “last mile” problem. Integration of these AI-driven systems into our society remains a grand challenge: they not only need to perform transportation tasks, but also to do so in close proximity with humans in the open world. AI implementations are not safe and do not convey trust in the population due to unacceptable fatal accidents involving self-driving cars. Delivery/social robots face similar issues, either freezing in crowded scenes or recklessly forcing humans to move away. To address these challenges, AI must go beyond classification tasks and develop broader cognition: learn and obey unwritten common sense rules and comply with social conventions in order to gain human trust. Robots should respect personal space, yield right-of-way, and ultimately “read” the behavior of others to effectively navigate crowded spaces. I will present a new type of cognition I call socially-aware AI to address these challenges.