This paper is part of a wider research project on Paradoxical Spaces: Encountering the Other in Public Space that explores how cultural difference is practiced and negotiated in different public spaces in Copenhagen. The present case focus on encounters at two urban festivals: Kulturhavn (Cultural Harbur) and Smag Verden (Taste the World)—both multicultural and both initiated by the Municipality of Copenhagen. The festivals are seen as sites for ongoing dialogue and negotiation of identity and belonging. The celebration, performances, and pleasure of festivals can empower the body, break down social and cultural distance, and for a moment suspend everyday life. They are related to laughter and freedom, but can also be exclusive, alienating, and a vehicle of the inserting of the hegemonic order. The aim of the paper is to discover how the festivals work as social and material mediators of cross-cultural encounters—how they give rise to different modes of encounters and how they balance between liberation and similarities. They are both organized by the municipality of Copenhagen, who invite voluntary organizations and cultural associations every year to participate in organizing the two festivals. They both cover a broad range of cultural activities such as dance, music, food, sport, and theatre, and they share the vision of celebrating the cultural diversity of the city. We chose these two festivals in order to explore variations in the way the festivals are experienced and encountered; the focus of the analysis is on how festivals with many similarities in location and formal conditions can give rise to rather different modes of encounters. The aim of the paper is to explore how the festivals work as social and material mediators of cross-cultural encounters. How do the two festivals give rise to different modes of encounters? How do they balance between liberation and domination in a differential way? Drawing on empirical material obtained through participant observation and framed by theoretical conceptualization of cross-cultural encounters, multicultural festivals, and aesthetic politics, the paper explores embodied encounters at the two festivals. It focuses on the role of the festivals as social and material mediators of encounters and negotiation of identities. The paper concludes on the paradoxical character of the festivals, involving antagonistic embodiments of performance, pleasure, and politics.