This chapter responds to the broad question of how gender and affect can be co-thought in studies of mobilities and transport. We regard transport and mobility systems as affective structures, where man–machine complexities are being performed. In this chapter, we exemplify these relations, focusing on how cyborgic entanglements of man–machine, transport and affective structures are staged, and enacted in selected historical, contemporary and future cases. We argue that emotion and affect are strong motivational powers that regulate how we travel, in what way we travel and how we appreciate different means of transportation. Last, we discuss whether the current and coming automatization of automobility can possibly disrupt rather than reify the historically strong connection between masculinity, the power of engines, speed and risk. Our question is: as the affective structures of automobility are anticipated to change when future forms of automobility will be more about “passengering” in automated and connected mobility systems, will this also fundamentally change the driver/technology relation?