This workshop offers care-oke, a singing orchestra of care, as a design method and ritual to simultaneously manifest and probe care of self, care of others, care of community, care of matters of care in collaboration. We argue that such silly-serious approaches have an important role to play in injecting vulnerability, social risk-taking, feminist ways of knowing into complex change work addressing complex global challenges. Participants will experience coming together in care-oke, and reflecting on what singing as caring can mean for design cultures and collaborations.