Total Recommendations: 1
If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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...then you might like
Youkoso Jitsuryoku Shijou Shugi no Kyoushitsu e
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When I first started watching this anime I immediately thought of Oregairu. They are both pretty similar to each other in terms on their school setting and main characters. Hachiman and Ayanokouji are both loners, observant, and they have that pessimistic vibe. Yukinoshita and Horikita aren't quite loners, but they're definitely anti-social and intelligent. Yui and Kikyou want to be friends with everyone, but they have some differences. Youkoso and Oregairu are definetly similar, and if you like either of them you'll probably enjoy the other.