In this conversational interview with Jessica Benjamin, who herself is a grandmother of feminist and relational psychoanalysis, we explore the scopic field of grandmaternal subjectivity. Starting with Benjamin’s recognition theory and thirdness, we consider how interrelated these positions are with maternal subjectivity, and then expand out to other layers of recognition by and of grandmothers, emphasizing where the grandmaternal can foster a sense of innate goodness in the mother through recognition. Benjamin is clear to not exclude fathers or grandfathers in her recognition of multiple subjectivities. She also considers the ways in which generational distance and age play a role in emotional regulation around young children, and broader social issues pertaining to recognition. We conclude with a consideration of lineage and relating through differentiation on both a personal and professional register.