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im completely stuck. originally tried going with the kate route but it just evolved into infinite circle of going to school>work>sleep without any cutscenes or such, any way to fix?

In my experience playing the game, there's three possible options.

1. You need to go to a specific location at a specific time for the next event.

2. You need to contact her first.

3. You made a wrong decision and accidentally closed off her route.

For the Kate route, you have limit the "corrupt" things you do (at least in the Cafe or around Kate)

You can leave your shirt buttons open, but you need to discourage Kate from doing so.