Learning happens not only in schools, but also in every context that affords new experiences and opportunities for metacognition. We aim to maximize the different activity-milieux in which learners are engaged in developing their life-long learning dispositions to learn within and across contexts. This paper is a follow up of an earlier published paper in which a framework on interpreting learning as how the self interacts with phenomena and reifications was proposed. Grounded in this learning framework, our research seeks to expand the "within context" learning to "across contexts" learning with evidence from a case study examining a 10-year-old boy's learning process. Through the case study, we will describe the interplay between bowling and schooling and how strategies learned from one context is situated into another drawing upon Ito et al.'s (2010) developmental trajectory of "hanging out-messing around-geeking out" perspectives. The findings show that for learning to be meaningful and authentic for the twenty-first century, it is essential for the learner(s) to be in constant dialectical interactions and relationship with oneself, others, and with the social-cultural artifacts that afford the learning. We conclude with practical implications derived from the study.