The marker bitte plays a crucial role in Contemporary German, especially in lay linguistic discourse on politeness (= first order politeness). This is in contrast to a research gap regarding the evolution and use of this element. Based on corpus data, the present study aims to trace the formal and functional development of bitte ‘please’. The analysis is based on a randomized sample of verbal bitten ‘to ask for’, nominal Bitte ‘request’ and syntactically reduced bitte ‘please’ extracted from fictional texts of the DTA and the DWDS core corpora covering a time span from the 17th to the 21st century. Contrary to previously proposed scenarios, the data suggest that syntactically reduced bitte developed in the late 18th century from an external modifier that primarily preceded imperative requests. As an internal modifier, the marker has been successively integrated syntactically and graphemically since the 19th century. From a pragmatic perspective, bitte has evolved from a deference marker. In Contemporary German, it can be described as a directive marker rather than a context-independent politeness marker.