Drawing on social constructivist learning theory and a conceptual framework for meaningful physical education (MPE), the purpose of this self-study was to present and explore how one teacher-researcher (TR) evolved their approach to implementing pedagogy promoting MPE in an alternative secondary/high school education setting. Utilizing self-study, data were collected before, during, and after twenty 75-minute lessons over 15 weeks. One critical friend interview, 20 post-teaching reflections, 18 observations, and 22 journal entries were conducted. A deductive and inductive approach utilizing the "Miles, Huberman and Saldana Framework for Qualitative Data Analysis" (2014) was implemented, with thematic analysis then applied. The following themes were constructed: bringing the fun; steering between sparkling and sensitive social interactions; co-creating and reconsidering challenge; monitoring movements toward motor competence; and pursuing personal relevance in physical activity. Findings demonstrate the TR's explicit and intentional efforts to better implement the concept of MPE within their planning and pedagogy to develop a better understanding of what this looked like in practice and the role each feature played in teaching and learning. Utilizing and promoting democratic and reflective practices led the TR to consider and apply these features more frequently and readily to better teach knowledge, attitudes, and skills to their students through the conceptual lens of MPE. The experiences presented and discussed demonstrate the benefit of doing so not just for the TR's evolving approach to teaching and learning in physical education, but indeed for the learning of their students, researchers, and other practitioners too.