A survey ("n" = 410) revealed statistically significant gender differences between middle school students' preference for playing particular types of games. Subsequent instrumental case studies theorised the "within-game" and "out-of-game" experiences of two middle school students as they played a digital hand-held game. These two case studies comprised stimulated recall sessions and subsequent follow-up, open-ended interviews. The analysis described the influence digital game playing can have on a participant's mathematics sense making. Findings included distinct differences in both the approach and the strategies employed by the respective participants to not only engage with the game, but contextualise it within their own knowledge and experiences. Furthermore, the study demonstrated the extent to which game playing can be a catalyst for further learning outside the game experience.