Masamune is so absorbed in himself he’s not noticed that she took things from that event way worse and has been completely miserable ever since. While he although consumed with desire for revenge better himself she wen’t the opposite rough and let it consumer her to the point of being just barley functional as a social human being.
Taking “revenge” on her at this point would just be cruel. Hopefully he comes to that conclusion at some point.
i get that it's for the "plot", but why even bother holding a contest between the two plays to see which one would be chosen. you've already forced the two classes to go through all the efforts, just have them both be presented