 If you liked
Ore no Kanojo to Osananajimi ga Shuraba Sugiru
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 ...then you might like
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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School comedies with a main character that has stopped believing in love. Then, he is forced to join a club with a girl that often has a bad attitude.
Both of these anime contain similar styles of commentary and comedy. They both center around the male narrative of a guy who's had a fantasical past he's tried to put behind him. The main character often has long monologues with himself with a metaphorical cynicism of the social order and events at school. Other than that both main characters also are a bit socially inadept and seek (or forced to seek in Hachiman's case) the help of a very intelligent girl also dealing with her own problems. Both anime take place in a high school club focused on self-improvement.
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Recommended by yngtadpole
Both feature a cynical guy jaded about love who is forced to join a school club. Both play with the standard high school love comedy tropes and feature witty dialogue and a sassy female lead.
In essence, both series takes place at a school life like setting. However, the main male protagonist gets caught up with a female protagonist who seems to have a strong independent personality.
The main male protagonist from both series are also considered anti social and rejects the idea of love. Similarly, the main female protagonist comes off as a cold beauty.
Both series also involves a club at school. This club consists of the two main characters as members although with different objectives.
The series also makes usages of comedy with humor through dialogues and interactions.
In both stories, "anti-social" protagonists are forced to join a club with one guy and a couple of girls.
Also, Yukino in oregairu strongly resembles natsukawa in oreshura in that they are both beautiful, sharp-tongued tsundere.
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Recommended by bunny1ov3r
Both are comedy, romance, school;
Both have characters with fanciful thoughts;
Both main characters (Yukino and Masuzu) are objective, they go straight to the point;
The characters form clubs to help others;
Both have characters with problems to relate to people.
They are almost exactly the same.
Anti-social guy who had a past case of Chu-2 Byo.
Female lead have the same personality, and characteristics.
school setting,harem.
Both involves a guy who is seemly an emotional masochist which despite of the females character's bad attitude still stick to her.
Male lead who does not seem to care much for relationships or love.
Chiwa and Yui look similar,and are both outgoing. Yui reminds me heavily of Chiwa(mostly due to looks)
Both comedy and romance.
A club is formed(or existed, in the case of Oregairu) with the intent helping others(Maidens club to be popular, Volunteer club to help others in general)
Both have same type of Male MC . They both are intelligent and cool creatures that i admire and they see realistic precept of the society .
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Recommended by IsekaiNekko
First of all both are light novels based anime which are fairly popular in Japan. Protagonists of both anime are both loners and the main heroines of both are ice cold beauties with almost similar nature. They both seems to be light heart comedy but are very dark at the core. They are both based on High School life.