As playing digital games has become a popular pastime among older adults, the study of the older audience of digital games would do well to exchange exploratory research for more specialist and focused areas. This article follows this reasoning and focuses on game enjoyment in later life. This topic is explored through two qualitative studies with actively playing older adults. The first study (n = 35, aged between 49 and 73) took place in Flanders (the Dutch-speaking part of Belgium), while the second study (n = 40, aged between 44 and 77) was held in the U.S.A. (Virginia and Kentucky). Using the principles of Grounded Theory, three interpretations of game enjoyment in later life were identified, namely, telic, hedonic, and eudaimonic enjoyment. The article offers a number of design recommendations based on its findings and discusses how the interpretations are influenced by context and player gender, and are subject to change throughout the lifespan of an aging player.