 If you liked
Sakura-sou no Pet na Kanojo
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 ...then you might like
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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Romance, comedy, school. And, both animes have great personalities for their characters. What's not to love?
Both inflicts the pain of reality
Both have great transitions from comedy to drama not like Golden****
Sakurasou- Great(talented) people overwhelm hardworking people
Yahari- People bring down other people
Yukino/Shiina - both are emotionless but are complete geniuses
Aoyama/Yui -hardworking both like the male protagonist
Both give great lessons about sacrifice,pride,talents and how to manage Friends/People
In both series, there is a theme of "special" club, who don't fully match. The characters are quite unique character and similar like: for example, Yui <-> Aoyama, Yukino <-> Mashiro. The main male characters are different, because Hachiman is quite specific view of the world, than Sorata. The titles are based on the ties between the characters and everyday life as well as in the two series were captured social problems. In both series is a little comedy and romance.
The protagonists either try to find solutions to their problems or want to change themselves for the better. Both feature romance with little complications.
Both can be insanely funny in how people thinks different about each other. But then eventually as the story goes on they start to accustom to each other. They also have a very similar style in 'Romance' as it's not overdone.
What makes both the shows similar :
1. Both deals with problem faced by the teens growing in the society.
2. None of the anime solely focus on romance.
3. Many characters from both the shows face the same family problems.
4. Both shows highly focus on character's psychology and their mentality.
5. Both shows have a good balance of comedy,romance and drama.
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Recommended by Animelia99
Both Sakurasou and Oregairu delve into the problems and difficulties high school students will face. While Oregairu focuses mostly on the social problems and what happens presently, Sakurasou focuses a lot more on what each character will do an choose for their future. Overall, both are unique and entertaining romantic comedies.
Both anime start off as light hearted comedy focusing around daily lives of (mostly) normal teens. However, they both develop into fantastic drama based anime that focus on the realities of students. Sakurasou is better, but Oregairu is undoubtedly amazing too.
Both titles got romance, comedy, and drama as main themes. Both are showing the hardships of everyday life in their teenage years in their own original way. Some characters are quite similar personality-wise. The vibe of both shows is very similar.
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Recommended by iHateAnimeBro