Elderly people often struggle to keep up with digital advancements, particularly given the fast pace of such developments and the increasing need to interact with novel devices in everyday life. To include elderly people in ongoing socio-technological developments, we aim to overcome the barriers to learning and adoption such older adults may face. In this contribution, we set the methodological stage for an interactive game-playing approach using touchscreen tablets. By using games in learning settings, we encourage elderly people in digital adoption and skill development. In a first study, a video analysis of game-playing sessions and active learning support were performed. Although approaches that combine game-playing with learning could encourage elderly people to become an integral part of a technologically advancing society, the facilitation of interaction processes in individual and collective gaming seems to be crucial. We report on the performed field study and provide methodological suggestions for investigating digital media adoption.