One third of Estonian residents identify Russian as their mother tongue, and despite having lived in Estonia for decades, many of them are not fluent in the Estonian language and choose to remain stateless rather than obtain Estonian citizenship by passing the state language exam. Ethnic segregation in Estonia continues to be a matter of bitter political debate, not least in the context of tensions with neighboring Russia and pressure from the EU to solve the problem. While a lot of state resources are being spent on what the Estonian-speaking public often perceives as vain attempts at integration of Russophones, several civil society initiatives have recently emerged to provide platforms for informal language socialization. In this article, I focus on the case study of the Keelegrupp (Language Group) which provides a venue for interaction between Estonian and Russian speakers, to analyze what makes this informal organization more successful at responding to the challenges of language-based segregation than professional, state-funded initiatives. Ethnographic documentation and analysis of this initiative is essential given that its experience and structure are highly applicable for and transferrable to many other states with similar situations of ethnic segregation, not the least the neighboring Baltic countries.