In this paper we present a field study that took place in the environment of the exhibition “Stefanos Rokos: Nick Cave & The Bad Seeds’ No More Shall We Part, 14 paintings 17 years later”, hosted at the Benaki Museum (May 2019). A group of visitors played the game “Find the Artwork behind the Story!”, crafting stories over the displayed artworks and sharing their thoughts, reasoning and emotions. Then the artist, Stefanos Rokos, joined the group and a new game round was played. We investigate how the artist’s participation affected the group experience, examining both the visitors’ and the artist’s perspective. Our findings show that the visitors were willing to share their stories and highly appreciated their gameful interaction with the artist. We observed that the artist behaved similarly to the rest of the players, rejecting our hypothesis that he would take on a leading role in the discussions. The artist expressed his enthusiasm for the game experience, stating that his participation in the game helped him better understand how the visitors see and discover his artworks. Overall, both sides reported that the game fostered the interaction between them, providing an engaging social cultural experience. Finally, we summarize how the results of the study drive the next iterations of the mobile application so as to support the artist’s participation in the game, and we describe our future steps.