In this qualitative case study of one tutoring relationship, I present new data on the extracurriculum; investigate tutoring as it occurs in community spaces; and argue that individuals can connect across systematic inequalities through personal conversations around picture books, photographs, and other visual and textual materials. Rather than ignore individual positioning within institutionalized power and privilege, tutors and writers can strengthen relationships and make tutoring more effective by evaluating how the systematic becomes personal and intimately known in one-on-one conferencing.