We present a critically focused, semester-long community engagement project entitled "Intergenerational Connections" as a form of critical interpersonal and family communication pedagogy (CIFCP). The project utilized Zoom to connect small groups of undergraduate students in the US enrolled in a course on relational communication with older adults in a long-term care facility to dialogue about close relationships. We were interested in how dialogue across generations maintained or altered students' attitudes and expectations about communicating with older adults and analyzed student reflections before, during, and after the dialogues using a turning point analysis. The study was framed using Social Identity Theory (SIT) to show how young adults may label older adults as an outgroup contributing to negative stereotypes. We discuss two turning points related to "Perceptions of Aging and Developmental Changes" and "Understanding and Expectations of Relationships" and identify practical implications of the project for universities and communities.