This study is grounded in a social-cultural framework that embeds learning in social activities, mediated by cultural tools and occurring through guided participation in the social practice of a particular community. It uses conversation analysis as a tool to examine the structures of the talk-in-interaction of naturally occurring conversations between 11 pairs of older adult (aged between 65 and 92) and undergraduates (aged between 18 and 25) during a 6-week social practice of intergenerational digital gameplay. The purpose is to demonstrate how older adults adapt to and make sense of collaborative gaming activities through guided participation. The features of minimum gap and overlap, even conversational inputs, and orientation to one another’s turns indicate interactional connection between older adults and younger people. Adjacency pairs in the form of question-answer and self-initiated other-repairs are the situated use of social resources afforded by the intergenerational interaction. It is through these two main means of interaction that younger players offer immediate feedback and explanation to guide older adults to engage in the collaborative play and develop understanding of unfolding concepts and phenomena.