This study examined how the accommodative environments experienced from grandparents and grandchildren’s own age-related communication are indirectly associated with grandchildren’s life satisfaction, depressive symptoms, and loneliness, via grandchildren’s self-efficacy with respect to aging. The communication experienced from grandparents was classified as accommodative, ambivalent, and mixed-accommodative chatter. Grandchildren were classified into engaged, disengaged, bantering, and disengaged-joking profiles based on their own age-related communication. Grandchildren who experienced accommodative chatter were likely to be engaged and disengaged communicators about age-related issues; grandchildren who experienced mixed-accommodative chatter were likely to be bantering communicators about age-related issues. Relative to engaged communicators, disengaged-joking communicators demonstrated lower life satisfaction, more depressive symptoms, and greater loneliness, via lower self-efficacy with respect to aging. Patterns of accommodation and nonaccommodation from grandparents may place grandchildren on specific trajectories for communicating about age, and grandchildren’s own communication may be consequential for well-being even at relatively young periods of the life span.