Recent articles have noted that humanities computing techniques and methodologies remain marginal to mainstream literary scholarship. Mark Olsen's paper discusses this phenomenon and argues for large scale analyses of text databases that would incorporate a shift in theoretical orientation to include greater stress on intertextuality and sign theory. Part of Olsen's argument revolves on the need to move away from the syntactic and overt grammatical elements of textual language to more subtle semantics and meaning systems. While provocative and important, Olsen's stance remains rooted in literary theoretical constructs. Another level of language, the cognitive, offers equally interesting challenges for humanities computing, though the paradigms for this type of computer-based exploration are derived from disciplines traditionally removed from the humanities. The riddle, a nearly universal genre, offers a window onto some of the cognitive processes involved in deep level language function. By analyzing the riddling process, different methods of computational modelling can be inferred, suggesting new avenues for computing in the humanities.