This paper explores how a teacher preparation program in a liberal arts institution built upon the foundations of dialogic, relational pedagogy utilizes strong alumni connections to improve teacher education curriculum and support preservice, inservice, and teacher educators as they work to teach against the grain. Best visualized as an infinity symbol, we describe the ways our recursive mentoring loop supports ongoing, fluid collaborations between PK-12 schools and our teacher preparation program and discuss how maintaining and nurturing relationships with alumni experiencing new teacher socialization in many school contexts is mutually beneficial in supporting both preservice and inservice teacher development. We share three case studies of value-added experiences in which our alumni engaged as we reimagined the traditional temporal boundaries of teacher education. The recursive mentoring process invites each party to see how one's aspirational education philosophy can be maintained even when it might go against the grain in a given school context. These relational, dialogic spaces foster teacher agency and collaborative problem-solving in schools and spaces of higher education.