Many tabletop game enthusiasts report not actively pursuing victory when playing with new players in order to provide a positive gaming experience. Does self-handicapping affect the preferences and future play intentions of beginners? In this experiment, an experienced player taught a tabletop game to new players and played with them. Participants (N = 60) were assigned to one of three conditions: control (experienced player actively pursues victory), overt self-handicapping (experienced player restricts her choices and announces this to the new player), and covert self-handicapping (experienced player self-handicaps without telling the new player). Participants then reported their gameplay experiences and their interest in playing it again. We discuss the study results and implications for game-based interventions.