Japanese bishoujo videogames take on the characteristics of highly detailed “choose your own adventure” novels. The current case study seeks to present a series of “classic” bishoujo videogames and explain how they function to orient the Western player to the culture of modern Japan through the phenomenon of telepresence. Aspects of telepresence that include transportation and immersion are considered toward the end of offering the player a degree of access to some aspects of modern Japanese culture. It is suggested that, by experiencing a sense of telepresence through inhabiting a Japanese avatar, the non-Japanese player has the potential to obtain a heightened level of competence in negotiating Japanese culture.