However things get complicated when, following a brief encounter, his sister, Chie Ashikaga, introduces him to Roka Kitsuregawa, an acquaintance who also becomes infatuated with him. Despite already having a boyfriend, she genuinely reciprocates his interest.

Yuuki Ashikaga is a high school freshman in his second semester at Sakakino Academy, who from his regular visits to the school library, grows enamored by Kotonoha Katsura, a fellow classman who comes by to read. All signature characters and their established relationships appear in the game, with a sextet of new cast. As such, the undisclosed location of the story remains the same with focus made prominently on campus. Unlike in Summer Days, the story in Cross Days is not rewritten as a spin-off of the original story, but occurs during the events of it, making the game a parallel series to School Days. The game is audibly stereophonic with lip-synched voice acting, sound effects and background music. Artwork is noticeably crisper and anti-aliased, colors are far brighter and vibrant and motion is slightly more fluid and articulate.

Like its predecessors, Cross Days is presented with, considerably improved, limited animation. In order for the player to watch all the possible endings, he or she will effectively have to replay through the game several times, making different selections along the way.

These choices are intricately linked to alternating routes of plot, moderately changing the direction of the story as each is made, ultimately leading to erotic scenes between characters and one of various endings. Cross Days, in typical visual novel fashion, is essentially played by watching and listening to episodic sequences of story and then selecting, or ignoring, clickable actions or responses when they are presented to the player.

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