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Cinnamon
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How can he hate anime so much while still being able to say "Anime A is exactly like Anime B because _________!" That suggests that he's at least watched Anime A. Gaaaahh...
Anyway, I would suggest Gankatsuou. It might be jumping into the deep end of the pool, but I loved it. I really liked that they made their own adaption of The Count of Monte Cristo.
Also, Boogiepop Phantom. It's a mind trip anime, with eerie/horror-type elements to it. I enjoyed that one quite a bit as well.
Or hell, you could have him watch Excel Saga, which pretty much makes fun of different types of anime and games, all while celebrating them. That, and it's so funny.
Just my suggestions. Surely there's other great ones out there, too.
Also, this is hereby an Orihime pairing thread. <3
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