 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
Ao Haru Ride
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Even if one is a Shoujo and the other is sort of like a Seinen, the two share many similarities. They both revolve around troubled teenagers and their difficulty making friends. They both tap into questioning how they should deal with their social lives. To sacrifice their own values just to make friends or not? To be honest to themselves and other people or to sacrifice that just to avoid being excluded from the group? Yahari goes a little deeper though. The male main characters are also both very pessimistic. The upbeat female main characters are also both..well..upbeat.
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Recommended by BiddingGortonio
The main male characters in both anime are very pessimistic thus giving off quite a depressing vibe. They both do give some pretty good advice though when "helping" others. A love triangle is also present in both anime. While both anime are Rom-coms, Oregairu tends to not focus on romance as much as Ao Haru Ride.