Purpose: Acknowledging the growing ethnic and cultural gap in diverse teacher and student populations, this study examined the pedagogical experiences of undergraduate physical education teacher education seniors following a teaching experience at a youth development center. Method: A phenomenological case study approach was employed in which preservice teachers taught and participated in over 45 secondary physical education lessons. The primary data sources were reflective journals and semistructured interviews. Results: Two major themes were constructed that describe the journeys of the physical education teacher education seniors teaching at both the youth development center field experience and in their internship placements the following semester. Initially, the preservice teachers experienced nervousness, uncertainty, and concern but, across time, experienced a degree of change and growth that saw them becoming particularly aware of and appreciating the personal biographies of their students. Discussion: The extent to which the physical education teacher education seniors' experiences at the youth development center were transferred into their internships is discussed in addition to implications for introducing culturally relevant pedagogies in nontraditional settings.