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Systematic age-related neural dissimilarities in processing dynamics and strategies raise fundamental questions about how the human brain supports cross-generational communication, especially in light of accumulating evidence linking interpersonal similarities in brain responses to communicative success. Yet despite its prevalence and tangible health-related importance, naturalistic intergenerational communication involving older adults is understudied. In this paper, we lay out why filling this research gap is critical in advancing our understanding of naturalistic communication, with implications for both science and practice.