This study investigates the effects of cultural orientation and the degree of disdain for robots on the preferred conversational styles in human-to-robot interactions. 203 participants self-reported on questionnaires through a computer-based online survey. The two requesting situations were intended to simulate the participants’ interactions with humanoid social robots through an Internet video-phone medium of communication. Structural equation modeling was performed to examine the mediating role of mechanistic disdain between multicultural orientation and conversational constraints. The findings reveal that between the two dimensions of multicultural orientation, only open-mindedness inversely influences mechanistic disdain. Mechanistic disdain, in turn, negatively affects three face-related conversational constraints, thereby leading to a lesser concern for robots’ feelings, for minimizing impositions on robots, and for avoiding robots’ negative evaluations. The implications of our findings on humans’ relations with virtual robot entities and on the future development of humanoid robots are discussed.