 If you liked
Ore Monogatari!!
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 ...then you might like
Naze Toudouin Seiya 16-sai wa Kanojo ga Dekinai no ka?
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Inexperience in romance. Both series' main male protagonist falls into that category when it comes to developing relationships. Throughout their past lives, they have been rejected by girls for various reasons. In present time, that pattern seems to continue but some events unfolds that changes that. Both series are known for some cliche story developments but remain genuine to their premise and intentions. There's also a good amount of characterization as we see what our main male protagonist is really like; although their personalities aren't very similar. Recommended for fans of comedy/drama/romance.