History Woobie / KatawaShoujo

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** Hisao Nakai, the protagonist. The game begins with him about to receive a LoveConfession from the girl he's always liked, only to suffer a heart attack. He's hospitalized for four months, and after six weeks, his old friends and his love interest stop visiting. At the end, he ends up in an unfamiliar school, and his disability leaves him at risk of a heart attack if he overexerts himself or even has any strong impacts to the chest.
** Emi Ibarazaki lost her legs below the knee in a car accident [[spoiler:as well as her father]]. Even though she has regained her ability to walk with prosthetics, she still suffers nightmares, and it's implied that part of the reason she runs is to banish them from her mind. Despite seeming outgoing and cheerful, she lets very few people close to her, for fear of losing them.
** Hanako Ikezawa. Between the horrible burn scars, the dead parents, and the crippling social anxiety, you can't help but want to hug the poor girl. Even though she runs away in a panic when you first try to talk to her. Maybe ''because'' of that, actually. [[spoiler:Surprisingly, her route deconstructs this. Her woobieness is initially why Hisao wants to become closer to her. Hanako is well aware of this and she does ''[[DontYouDarePityMe not]]'' like it.]]
** Lilly Satou was left behind in Japan with her sister Akira by their parents, and her relative maturity for her age is a result of having to become more independent as a result of Akira's shortcomings as a single parent (Akira admits that it's unreasonable to expect a 19-year-old to raise a blind girl alone). [[spoiler:Late in Lilly's route, their parents order the sisters to come to Scotland permanently, leaving behind their boyfriends in Japan, and causing no small amount of heartache]].
** Rin Tezuka suffers from difficulties making herself understood in social interactions and art, causing her a great deal of pain. She also struggles with what it means to be an artist, and fears that she will change herself to someone she is not in order to succeed. [[spoiler:Later into her route she starts acting self-destructive (not sleeping, not eating right, smoking) to try and find inspiration for her art.]]
** Shizune Hakamichi grew up with an abusive father who belittles her, has no respect for her accomplishments and refuses to learn sign language to speak with her. Despite her wishes to make people happy, she often comes off as overbearing and bossy, partly due to her SpiritedCompetitor personality and partly because of communication problems caused by her deafness.
** Even [[spoiler:Misha]] turns out to be one. [[spoiler:She is in love with Shizune and confessed to her; she was rejected, but Shizune continued to seek her out for friendship, which only caused her pain. Things got worse when Hisao started becoming closer to Shizune.]]

** Rin Tezuka suffers from difficulties making herself understood in social interactions and art, causing her a great deal of pain. She also struggles with what it means to be an artist, and fears that she will change herself to someone she is not in order to succeed.