This paper offers a qualitative and quantitative analysis of French and Italian wh-in situ questions based on spontaneous spoken data. A pragmatic analysis relying on two parameters, propositional activation and pragmatic functions, reveals that the licensing conditions and the use of this structure largely differ in the two languages. While French wh-in situ do not require an activated proposition and can introduce a discourse-new topic, Italian wh-in situ mostly require an activated proposition and, at least in the analyzed corpus data, do not introduce discourse-new topics. An examination of the context also reveals that the different licensing conditions influence the interactional uses of these questions. All in all, both French and Italian wh-in situ require a pragmatic condition, which is their ‘anchoring’ to given, or at least inferable, information in the linguistic context (as is typical of Italian) or to predictable situations in the extralinguistic context (such as expected discourse moves in social interactions, as is the case for French).