This paper describes the early-stage prototyping process developed to probe into the socio-cultural dimensions of the Co-Drive project, which is a new service concept for traveling and socializing by car between a real driver on a semi-automated car and a remote passenger connected via virtual reality from home. By focusing on the intertwining journeys of the two actors of the experience, the driver and the remote passenger, three key interactions have been isolated and addressed as separate prototyping interventions in the wild. Such a seamful prototyping strategy enabled the users to experiment the whole service although the technology was not yet completely developed, and more specifically it allowed them to accommodate and appropriate each part of the experience into their everyday activities, revealing initial evidences of the potential social impact drawn by a future deployment of the service.