The Playful Designer, my thesis project, is a proposition, a poetic approach for (re)design(ing) [in|with|of] social constructs. My work addresses the ethical awareness of the ways in which designers approach situations and invites more rigorous engagement aimed at challenging implicit bias, especially around the politics and positionality of "helping," authority, expert, or complicit collusion within oppressive systems. The term "playful" serves both as a provocation and a call to action. The Online Infinite Play Exhibition, the culmination of this thinking and making, is a combination of poetry, graphic and UX/UI design, and a playful and seemingly chaotic curatorial process. The exhibition affords an expansive, generatively confusing experience, composed of 57 parts that are connected in strategic but seemingly unexpected ways. It questions the value of “simplicity,” “reduction,” and “intuitiveness” as essential design properties. Instead, it relies on interpretable design dimensions to generate a sort of thoughtful disequilibrium and playful sense of responsibility — for these are critical characteristics of a more conscious, intentional, and free form of design(ing).