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Monika does love you and I think she should let it slide to let you win and make you happy if you want it badly enough to cheat. Going off of the Repeat Conversation>Games>Completionism conversation, I think it would be a better idea to have a much less harsh punishment if any, but offer some extra bonus text if you win without cheating. Yeah in MAS, Monika does say that she doesn't like cheaters but she says she understands that some people cheat because it allows them to freely explore something that would otherwise be too difficult. In the main game, you essentially kill her by deleting her and she will still love you.
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I never cheated in chess and I never planned to but I saw this code and although I can't speak for everyone, it bothered me a little bit that Monika would do this for you cheating in chess and it doesn't feel right. Not 100% sure if this is actually a thing but I heard that if you cheat enough, you would permanently ruin the MAS experience and would have to delete everything and reinstall the mod or at the very least would never be able to play chess again.
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I was looking through some code for MAS and saw what looked like the code for when you cheat in chess or something happens to the save.
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