Many philosophers of education emphasise the impossibility to really "solve" philosophical--and with that, educational--problems these days. Philosophers have been trying to give philosophy a new, constructive turn in the face of this insolvability. This paper focuses on irony-based approaches that try to exploit the very uncertainty of philosophical issues to further philosophical understanding. We will first briefly discuss a few highlights of historical uses of irony as a philosophical tool. Then we concentrate on two different interpretations of irony, formulated by Bransen and Rorty, that aim at gaining insight into how we make meaning of the world, while at the same time recognising that such an understanding would be impossible. After discussing some problematic aspects of these interpretations a third interpretation of irony is developed, based on a third view of the nature of meaning-making. Following these three interpretations, we will discuss their philosophical merits and the different kinds of insight they can produce for philosophy of education.