In this article, I offer a sociological user perspective on increased self-driving automation, which has evolved from a long history associated with automobility. This study explores complex, perceived a priori driving pleasures in different scenarios involving self-driving cars. The methods used consisted of 32 in-depth interviews with participants who were given eight video examples (two video examples within four different scenarios) to watch. A numerical rating scales formed parts of the interviews. The findings revealed that driving pleasure when using increasingly automated driving technologies is very complex and must be seen within various contexts, including, for example, different speeds, road conditions, purposes, driving distances, and numbers of people in the car. Self-driving cars are not just about technology, increased safety, and better traffic flow, but are also dependent on automotive emotions and complex perceived issues, which are full of meaning that go beyond the car itself. The highest driving pleasure in self-driving technologies was found for parking and traffic jam situations in the city. However, trust and the sense of freedom and control were major concerns in all aspects of emerging self-driving mobilities.