The article reviews the experience of the role-play simulation (RPS) 'Modelling negotiations between the EU and EAEU', arranged in 2018 and 2019. Its specific goals were building knowledge (about the European Union (EU) and Eurasian Economic Union (EAEU) and enhancing a transnational dialogue between EU (Western) and Russian students in the context of a deteriorated EU-Russian relationship. This latter aspect of international RPS has received insufficient attention in the literature, yet it might contribute to the improvement of real-life EU-Russian relations through fostering a transnational dialogue and mutual understanding among young citizens. The article outlines the setting of the RPS and addresses three major difficulties that the organisers faced (designing the RPS, preparing students and fostering their dialogue), the solutions that were developed and the assessments of the results.