This paper examines the Japanese dating simulator video game, Tokimeki Memorial Girl's Side, the first female protagonist version in the Tokimeki Memorial series. Analysis of the game mechanics, characterisations, player options and their results demonstrate that the game assumes and reinforces a range of cultural norms and social expectations in relation to gender performativity, courting and dating, relationships and intimacy. I discuss how the gameplay actively produces particular heteronormative perspectives on how girls and young women should enact femininity if they are to avoid being alone at the end of the game, and, for that matter, in life.