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Nozomu Itoshiki (糸色 望, Itoshiki Nozomu?)
Voiced by: Hiroshi Kamiya
The main character, a high school teacher and the youngest son of the Itoshiki family. He always wears a hakama and kimono abroad, preferring flippant casual western clothing in his hometown. When his name is written horizontally it resembles zetsubō (絶望?, "despair" wink , befitting his extremely negative, paranoid and pessimistic attitude. He often shouts "I'm in despair!" and attempts suicide several times, though rarely with serious intent. Most of the main girls seem to have feelings for him but only because they misunderstand what he said to them (during the episode about them). His negative personality started blossoming when he was in in his first year of high school when he 'accidentally' joined a 'Negative' club. He is based upon the main character from Dazai Osamu's No Longer Human, which is both Nozomu's and the author's favorite novel.

Rin Itoshiki (糸色 倫, Itoshiki Rin?)
Voiced by: Akiko Yajima
Nozomu's younger sister, a seventeen-year-old ikebana master. When her name is written horizontally it resembles zetsurin (絶倫?, "unequaled" wink , which describes her exceptional talent in various skills; however, calling her zetsurin evokes her fury, as the word is often used as slang for sexual prowess. She has revealed her willingness to marry out of the Itoshiki family in the hope of abandoning her unwanted name. Rin eventually transfers to Nozomu's school and becomes a student in his class, after which she frequently faces the readers/audience with her backside (in a parody Shin-chan, who is also voiced by Akiko Yajima). She also happens to own a chocolate factory.