This study aimed at identifying and interpreting relevant relationships between players’ perceptions of meaning-making affordances and: 1) players’ reported quality of the gameplay experience; 2) general player game ratings; 3) expert game ratings. The theoretical framework underpinning this study conceptualized gameplay as an iterative and contextualized activity driven by meaning-making processes that integrate rational interpretation and affective valorization of key game aspects. This was used to evaluate 14 games using an ad-hoc questionnaire that was completed by experienced players and compared to scores of game quality provided by the players and by external sources. The results of this exploration suggest an association between meaning-making affordances and critics’ evaluations, but not with players’ game experience and player ratings. The analysis revealed that key methodological issues should be accounted for when investigating game features and their affective meaning-making implications on the perceived quality of a game and the gameplay experience. Insights on important theoretical and methodological issues that may orient and support future research are discussed.