Identifying educational competencies for the 21st workplace is driven by the need to mitigate disparities between classroom learning and the requirements of workplace environments. Multiple descriptors of desired 21st century skill sets have been identified through various wide-scale studies (e.g., International Commission on Education for the 21st Century) and consistently within the context of science, technology, engineering, and mathematics (STEM) learning, the ability to problem solve, particularly complex problem-solving, remains a crucial competency. In this paper, we look at how current contemporary spaces such as the immensely popular, massively multiplayer online role-playing game(MMORPG), World of Warcraft, (WoW) afford problem-solving skill acquisition in the context of Singaporean youth learners. Given that WoW exists as a contextual space with an overarching narrativized problem to be solved, our investigation focused on two important related constructs that underpin learners’ problem-solving trajectory—learning and identity becoming within contemporary domains of technology learning. We present findings of an ethnographic investigation of one youth gamer within the affinity spaces of WoW. Moving away from traditional mentalistic construals of problem-solving, our findings indicate that problem-solving within WoW may be characterized by a triadic-D model of domain, disquisitional, and discursive practices within self, social, and structural dialectics. Theoretical considerations for broadening the understanding of a situated and embodied notion of problem-solving and identity becoming within STEM learning are proposed.