Culture can influence how people communicate and how they choose how to address others, according to different factors, such as the relationship between them. This is particularly relevant in the case of requests, because requesting involves a series of considerations, such as whether one has a right to request or not, or perceptions, such as how much the request is an imposition on the recipient, and these can be influenced by culture. These considerations and perceptions are in turn influenced by underpinning values and beliefs about appropriate behaviour, which can vary across cultures. Hence it is important to investigate how people from different cultures perform requests, and how they choose among different ways of performing them, including the different factors that influence their choices. This paper aims to investigate requests in Italian and British-English using roleplays where speakers enacted different types of requests. It also used follow-up interviews where the speakers were asked to explain how they interpreted the relationship between the requester and requestee, how much they considered the request an imposition on the recipient, how these views influenced their ways of speaking, and how they evaluated their own and the other’s linguistic choices, particularly in terms of politeness.