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I don't know what's happening in this it feels like they do a time skipped because in this aki has short hair and it feels like they are already dating plus they are already 3rd years on this while in the original series they are only 2nd years I think this is after the revenge
An aimless series of skits that, for all their meandering frivolity, would serve as a not unenjoyable reunion with the likeable cast of Masamune-kun's Revenge--were it not for the fact that, whether frivolous or narratively essential, this OVA (bizarrely) serves as a bonus reel for the Masamune manga, rather than a bonus/sequel for the Masamune anime. In other words: prepare to be entirely without the context to explain why the characters act (and look) juuuuuust different enough from how you remember them to make you feel like your friends have been hanging out without you. An unfortunate turn for those not in the know.