AbstractCulture can influence how people communicate and the reasons behind linguistic choices. However, the evaluativeprocess has been mostly neglected, particularly in comparative studies. This paper aims to fill this gap. It compares how two setsof participants, Italian and British-English speakers, rated own/others’ performances in roleplays involving different requestscenarios and it unpacks how their perceptions of sociopragmatic variables, such as social distance and request’s weight,influenced their evaluation process. Follow-up retrospective interviews were employed and content-analysed, to unpackparticipants’ evaluations. The results showed cross-cultural differences in importance, interpretation and expectations attachedto different variables and underlying values.