Total Recommendations: 2
If you liked
Chuunibyou demo Koi ga Shitai!
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...then you might like
Hana to Alice: Satsujin Jiken
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Okay Chunibyo is much more flashy and crazy than Hana to Alice, but it has that theme of new friendships and helping someone who is not all there mentally recover by solving a mystery. But most important of all the characters in Hana to Alice are definitely Chuunibyou.
Anime rec by Ready_Player_1 - Sep 15, 2015
If you liked
FLCL
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...then you might like
Arakawa Under the Bridge x Bridge
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FLCL deals with a group of crazy characters and one of them is homeless as well, I think.
Anime rec by Ready_Player_1 - Aug 31, 2015