This chapter explores playfulness as a cement of human bonds, and thus as a transformative pedagogical tool in educator-youth relationships. Drawing on personal experiences and theoretical insights from Punch (2003), Freinet (2006) and Katz (2004, 2011), amongst others, it argues that playfulness -the attitude that allows to disrupt the routines of any activity, including play and work- challenges hierarchical norms and fosters emotional bonds. The concept of a play-work continuum is used to highlight the emancipatory potential of shared, open-to-play work. Despite structural constraints, it is argued that a playful engagement opens a space for a critical reflection on top-down (re)educational models and capitalist paradigms of work (including school ‘work’), enabling youth to reimagine (re)education and work itself.