 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
Yamada-kun to 7-nin no Majo
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Both feature delinquent protagonists helping others. Both are harems that are heavier on story and drama than others in the genre. Both deal with similar themes.
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Recommended by MisterTrantastic
Both anime doesn't seems similar at first but change as the story developed. And these are what i found similar.
-The male protagonist was a loner. Except in oregairu, the protagonist become a loner by self choices while in Yamada-kun because he is a delinquent.
-The female protagonist was avoided by society because being a perfect student.
-There's unusual club activity
-The male protagonist was underestimated but turns out to be reliable.
Also, the school atmosphere felt similar. An elite school where intelligence is everything.
Both Main Characters (Hachiman and Yamada) are similar in the sense that they have similar personalities. Hachiman has his edgy and loner moments, while Yamada is pretty much a delinquent. They both have a mini Harem, with Hachiman having Yukino, Yuigahama, Iroha, etc. whilst Yamada has all the witches.
Both share well written and complex plots. People that were gripped to oregairu can definitely get hooked to this. Both underrated anime.
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Recommended by hour-friend