Studies from various disciplines have showed, that adding human characteristics to non-human object improves the interaction between human and this object. It can be assumed that human-like technologies have a positive influence on driver-vehicle interaction as well. This study investigates the potential to increase the willingness of truck drivers to cooperate during overtaking scenarios using anthropomorphized interfaces. Therefore, a driving simulator experiment was conducted with truck drivers. Two conversational agents have been developed, which differ in their degree of human characteristics. They supported the truck driver in the initiation and during the overtaking manoeuver by clarifying a willingness to cooperate and communicating the status of the overtaking process. The results indicated no significance in the drivers’ willingness to cooperate in interaction with the two agents. However, the perceived human likeness increased through the addition of emotionality and identity. More than half of the drivers were in favor of the more human-like agent.