 If you liked
Hige wo Soru. Soshite Joshikousei wo Hirou.
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 ...then you might like
Koi to Yobu ni wa Kimochi Warui
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Airing in the same season there are two different anime with two characters that have a huge age gap.
"Koi to Yobu ni wa Kimochi Warui" is about a playboy character that suddenly falls in love with the meek friend of his high school sister that makes him feel love for the first time.
He continues to curt her, by sending flowers and gifts while his sister plays the wingman to his antics and even the mother of the courted girl is amused by the stuff happening while the daughter is clearly uncomfortable with the 10 year older male making such advances.
The whole relationship is played of
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You start to wonder, how different western and oriental society are? Very controversial form many point of views, I enjoyed both because I found their stories quite uncommon.
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Recommended by Omar_Jordan
Romance between an office worker and a highschooler.
Koi to Yobu's MC is more on the creepy side, while Yoshida has morals.
As the celestial bodies align, and all matter beings to oscillate in crescendo fashion, or in other words, as the phenomena also dubbed "cliche" initiates, swiftly arranging our MCs to converge towards each other, yet comes a story of boy meets girl comes forward, though with a twist. The age gap!
Koikimo uses this twist to make for a marketed disgusting yet wholesome relationship, whereas Higehiro uses this for a time of learning, a time for the youth to reflect on their foolish imprudent actions. Both draw done to wholesome levels, and whilst the premise is off-putting, it is assured in both anime that there is
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Recommended by NextUniverse
Both series has similarity regarding the age gap of the two main characters. In Koikimo, the older guy falls in love with his sister's friend while it's the other way around where in Higehiro, the main girl wants to be noticed by the older guy.
If you are fed up with those traditional romance anime troupes and want to have something original with a new premise, then these series are for you.
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Recommended by Solaris-----
Similarities:
Same high school setting
The age difference between the Male MC and the Female MC
Wholesome relationship
I believe these shows are similar to each other, because they both discuss how relationships between adults and high school girls can be toxic and potentially illegal. As well as this they both acknowledge failures within Japanese society. However the angle shown is different in each show
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Recommended by ChizuruFan23
both are same huge age difference but still loveey dovey
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Recommended by VELVET_BLUES