Recently, radical democratic initiatives have been undertaken by freelancers and founders who come together in a range of alternative forms such as ethical entrepreneurial coalitions, urban coworking spaces, and open cooperative networks. In this paper, we argue that these initiatives to invent alternative, more equal forms of organizing engage strongly with relational activities to replace hierarchical interaction with distributed peer collaboration. While the literature has emphasized the sense of experimentation and reflexivity of these alternative forms of organizing, this paper especially (...) draws attention to the affective dynamics of everyday peer-to-peer collaboration. Drawing on an 18-month ethnography of a cooperative network of social entrepreneurs, we use a practice-based approach to study peer collaboration as a relational practice formed through a nexus of ‘weaving,’ ‘sharing,’ and ‘caring’ activities. Focusing on the affective orders enveloping relational practice, we document how the practice of peer collaboration is imbued by what we call an ‘affective oscillation’ forming contrasting amplitudes between confidence and frustration, exuberance and anxiety, and trust and exhaustion. As our core contribution, we problematize how the affirmative intent of radical democratic organizing is potentially jeopardized by this ‘cloudy affectivity,’ and we conclude that the collective pursuit of embodied ethical encounters is formed by slowing down and feeling into affective oscillation. (shrink)