This chapter sets out to explore the realisation of naturally occurring conversational requests in two languages (English and German). More specifically, the paper focuses on the head act strategies of German German (GerG), American English (AmE), and British English (BrE) requests. The data were collected in manual bottom-up searches in a corpus pragmatic function-to-form approach. While the majority of cross-cultural and cross-linguistic research on requests is based on experimental request data elicited by Discourse Completion Tasks (DCTs), the present study uses non-elicited (hence naturally occurring) conversational data to show the realisation patterns of the speech act. While previous research shows cross-linguistic differences with German requests being more direct, the results of the present study indicate a different pattern. In conversational requests, the preference for more direct head acts in German L1 populations reported in studies based on experimental data is either less pronounced or is reversed in that the GerG requests were overall less direct than both English L1 groups.