Dialog between drivers and speech-based vehicle interfaces can be used as an instrument to find out what drivers might be concerned, confused or curious about in driving simulator studies. Eliciting on-going conversation with drivers about topics that go beyond navigation, control of entertainment systems, or other traditional driving related tasks is important to getting drivers to engage with the activity in an open-ended fashion. In a structured improvisational Wizard of Oz study that took place in a highly immersive driving simulator, we engaged participant drivers (N=6) in an autonomous driving course where the vehicle spoke to drivers using computer-generated natural language speech. Using microanalyses of the drivers’ responses to the car’s utter- ances, we identify a set of topics that are expected and treated as appropriate by the participants in our study, as well as a set of topics and conversational strategies that are treated as inappropriate. We also show that it is just these unexpected, inappropriate utterances that eventually increase users’ trust in the system, make them more at ease, and raise the system’s acceptability as a communication partner.