you need to join the drama club first, and introduce that you like to watch movie, on a first day, go to the club, but on day 2 or 3 idc, just dont go to club or appoarch him, oh, in class, you pick "draw something", and then you do it yourself.
wait, when the game ask "write a love letter", write to anyone you like, so, you'll have yandere italy route success
(maybe,, i don't know how to giude you)