I’m under the impression we cannot move forward in the game due to a game breaking bug of the game that skips day 4 and goes straight to day 5, and that’s why we can’t move forward yet!
You absolutely can move forward with the game, you are just not selecting the correct options. I just finished completing the chapter and unlocked all the CGs. The hint they gave you is pretty much all you need to know... Try to make everyone happy.
i am unsure to be honest. if I remember right you kind of give mixed answers. some you flirt with him, some you don’t. i just tried a bunch of different combos til i got it.