Youth reliance on social media platforms as their main source of media consumption presents an opportunity to increase their cultural knowledge through engaging them in digital storytelling of their village oral history. This paper examines the results of a pilot study conducted in Palestinian villages with youth who were trained on local interviewing village elders to create digital stories. The process was designed in a collaborative game-like environment to obtain maximum engagement, thus creating a state of flow as stipulated by Csikszentmihalyi's flow theory. The surveys conducted at the beginning and end of the project, combined with ethnographic action research, demonstrate that it is possible for the youths' level of interest in the creation of the digital stories attains a state of flow when the process can be immersive and engaging such that a multi-phase plan that includes skilling then challenges at each phase -- not unlike a game.