 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
Just Because!
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Both shows delve into the personal intricacies of romance and interpersonal relationships at the high school age range and have a rather cynical lead character. Just Because has a stronger focus on the romance aspect while Oregairu has a more subtle approach. However, Oregairu also covers other social dynamics and digs deeper into its characters.
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Recommended by Samurai_Zero
These have basically the same premise. A love pentagon/triangle featuring an eternally bored-looking protagonist. (Hachiman and Eita are very similar in attitude, though Eita is much more laid-back about it all.) They both have plenty of drama and character building, though I would argue that if we take future seasons of Yahari Ore into account, Just Because! has better characters. Still, if you enjoy the premise of one you will likely enjoy it in the other.
this anime very similar with oregairu. both has a love triangle, mc with similar personality (i think), even the opening shared a same singer
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Recommended by coneundeur