Questions, and more specifically authentic questions, are at the core of dialogue-based learning and teaching. However, what is a question, and how can it be authentic? This paper addresses this problem by analyzing the distinct dimensions of questions, showing how their pragmatic nature is interwoven with the syntactic and semantic one, and how it can be grasped only by considering their dialogical functions. Questions are maintained to be proposals of different dialogue games (or types), pursuing specific interactional purposes, and potentially contributing to learning processes in different ways. By understanding how questions shape different dialogues it is possible to ask more suitable questions to the questioner’s goals. In this framework, the dichotomy between authentic and inauthentic questions becomes a strategic choice between different types of dialogical possibilities.