In this article I aim to explore the ‘playful’ use of language, primarily emphasized in improvisational practices. While improvisation is associated with abilities such as creativity and imagination, which require the possibility for free action, language practices do not function without being guided by rules. This raises the question of how improvisation can be thought of under rules. By drawing on Stanley Cavell’s reading of Wittgenstein, I will demonstrate that the relevance of our forms of life, as opposed to rules, allows for a reevaluation of the scope for improvisational actions without bypassing the ‘conventionality’ of actions and language. ‘Playing’ will then be understood not only as a matter of adhering to essential rules but also as guided by rules of competence, which create a space for acting freely. Finally, Cavell’s idea of language projection offers a fruitful perspective on the similarities between the improvisation of games and that of language practices.