This article concentrates on the analysis of requestive speech acts from the point of view of (im)politeness studies within the context of historical letter-writing. It draws its data from a sub-corpus of the Corpus of Irish English Correspondence (CORIECOR) containing letters written by Irish emigrants that settled in the United States and their intimates. The scope of this research is limited to intimate discourse to perform a cohesive study of the encoding of this speech act within a particular framework of usage in a particular genre. This study classifies a total of 254 requests extracted from this sub-corpus and observes the major tendencies that appear in this specific context. Results show a clear preference for the usage of impositive head act strategies (95.68% of the results). Imperatives (50.9%), want statements (27.8%), and performatives (9.8%) are the most recurrent head act strategies in this set of data. Conversely, indirect requests show a much lower number of hits (4.32%). Moreover, the data showed a preference for external modification or no modification at all. These results point towards the idea that directness might have been conventionalized as a sign of positive politeness between family members in the context of historical letter writing. Some reservations about generalizations with regards to the data are expressed and further research lines are proposed in order to establish a more solid understanding of the encoding of requestive speech acts in the context of historical letter writing.