Rebellious Asian Kid(t) is a practice-based research project exploring how humour can challenge hierarchy and foster safe spaces for dialogue within Asian families. Grounded in the cultural context of filial piety, saving face, and emotional restraint, the project investigates how communication design can mediate tension between authority and vulnerability. Through speculative artefacts such as the Survival Handbook in Asian Families and Decoding the Asian Mind card game, the research demonstrates how humour transforms authoritarian reactions into moments of empathy and reflection. Using an iterative, reflective design process, the study examines how humour can act as a compassionate strategy, disarming power structures while empowering connection. The outcomes show that design is not only a tool for communication but a medium for healing and relational safety. Ultimately, this project repositions communication design as a dialogue-driven practice that values emotional intelligence as much as creative innovation.