Cherry Jam is a visual novel with a slight inclination towards dating simulation. The hero is a nameless young man who is dating a girl named Tomoyo. The game is dedicated to their relationship, more precisely the dates they have together. As usually in visual novels, the basic premise is a flow of text accompanying still images, with occasional decisions that steer the story in a different direction. However, in Cherry Jam the player has to choose the protagonist's answers or actions very frequently. Those decisions influence Tomoyo's mood and eventually the outcome of the date. Many decisions also lead to a premature end of the game. The player also has to manage the protagonist's finances. Presents for Tomoyo and other expenses are deduced from the protagonist's overall wealth, so the player has to balance between keeping Tomoyo happy and not becoming broke. There is a "novel mode" in the game, which becomes accessible after the first game "death". This mode re-tells the entire story so far from the point of view of Tomoyo.
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