Anxieties concerning children's involvement in chatrooms have been heightened due in part to extensive media coverage of incidents in which teenage girls «run off» with older men. However, chatrooms and other virtual communities are also discussed as places in which new models of learning are occurring and young people are given opportunities to explore new ways of communicating and new forms of being. This paper asks what we can learn from exploring children's learning in chatrooms. Based on data collected at an arts centre in London, the paper analyses the interactions of four girls, age 10-13, as they engage in a chatroom (habbohotel.com). The paper shows how the girls are playfully taking risks, experimenting and negotiating meaning as they engage with discourses around pre-teenage girls. Our conclusions look at how theories of informal learning can help us to understand children's digital activities, and how these theories might be engaged with in educational settings.