This chapter explores the interplay of playfulness and precarity in AI-mediated languaging. Drawing on examples from social media users experimenting with generative AI, the chapter illustrates how AI reshapes communication, linguistic practices, and social interaction. These playful engagements demonstrate AI’s capacity to expand linguistic creativity and produce novel forms of meaning, while simultaneously revealing its fragility and the ethical tensions inherent in its use. By exposing the cultural assumptions, power relations, and value judgments embedded in AI systems, such moments highlight the non-neutral and unpredictable nature of AI technologies. The chapter argues that while AI opens up new possibilities for expression, it also demands critical reflection on issues of power, identity, and social norms. Ultimately, these examples highlight the ‘dis’engagement with AI’s potentiality while recognising and addressing the risks it poses to language and society.