In order to better understand the development of play and games in modern lives, this article examines two competitive leisure groups: digital fighting game players and traditional taekwondo practitioners. Drawing on qualitative offline/online interviews (n = 56) and close reading of externally documented life narratives (n = 14), we explore how the modes and motives of engagement fluctuate in competitive players over time. The study provides a new developmental approach to continuous competitive play as leisure. Our results show rather than making linear progress from ‘casual’ to ‘serious’ leisure, individuals in both groups perceive their lasting relationships with these activities gradually evolving through their lives in three stages: acquaintance, attachment, and accommodation, The players fluctuate between casual and serious engagement, occasionally reaching a state of subjectively meaningful and socially cemented life permanence. The study suggests that the patterns of long-term play and gaming may not differ much between digital and non-digital domains.