 If you liked
School Days
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 ...then you might like
Clannad: After Story - Mou Hitotsu no Sekai, Kyou-hen
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Both Kyou and Sekai offer training the main hero with their relationships with their girlfriends.
Also, Kyou and Ryou fell for the same guy, just like Katsura and Sekai, and get hurt because of that.
Written by Shirobake and LiCha.
-Both animes focuses very deeply into the story that involves love triangles and one-sided love.
-School Life
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Recommended by MagicFlier
similarities:
+ both from visual novel as one the available routes
+ same school romance setting
+ both 2 girls from both series have similar personalities, one is outgoing helping the other shy girl
+ similar meet up, date, and break up pattern
+ both picture Male MC as indecisive and pathetic
differences:
- School Days is far more dramatic and extreme than Clannad kyou-Hen
- while Kyou-Hen is shorter than School Days, the original Clannad is far longer and better than School Days
Love can hurt. It hurts those who are loved and those who are loving. There is no simple way to fix everything, it is particularly true when the relationship is complicated. School Days and Clanand AS Kyou Chapter understand this too much.
With both love stories being about how to choose between her and her, the two do a pretty good job at playing with emotion, one is quite evil compared to the other pitful clash.
I will leave it to you to see the ending, but I'd take these dramas if anything at the end of the day.
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Recommended by NextUniverse