Using dialogues with requests made by native speakers of Italian, the research we present in this paper tried to identify and analyze the perceptions of politeness of Brazilians and Italians and their possible motivations. We used a corpus composed by video and audio recordings in which pairs of native speakers of Italian perform role-play requests with low and high degree of imposition. We submitted an online questionnaire with eight videos selected from the above mentioned corpus to two groups of Brazilian (students of Italian at the beginning and at an advanced stage of their studies on the language) and two groups of Italian (living in Brazil and in Italy) informants. Based on their judgment about the videos, we tried to identify: if there were similarities or differences in the level of politeness attributed by Brazilians and Italians to the selected requests; which reasons informants gave to justify their choices; if there is a correlation between those choices and the reasons given to justify them; and, finally, comparing all these information, whether and to what extent prolonged contact with the other language and culture may change the perception of politeness of Brazilians and Italians. Our results revealed that there are more similarities than differences in the informants’ perception of politeness