The linguistic affinity is usually a great support grammatically, however, this does not always happen in the pragmatic plane, because this one is determined by cultural conventions whose divergences can put in danger the communicative effectiveness. The objective of this article is to explain with empirical data the importance of the development of a pragmatic awareness in the study of related languages. For this purpose, a study is presented that analyzes verbal politeness strategies in a corpus of request emails in Spanish and Italian in which university students make requests to their professors. The results come out that, despite the great linguistic and cultural affinity, emails from the Spanish and Italian academic contexts show different tendencies in the selection of verbal courtesy strategies and that the pragmatic characteristics of the L1 are reflected in the productions in L2.