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I've noticed that too that you have to visit them on each day of the week every time you unlock a new friendship level sometimes tho a cut scene only triggers a week or 2 later, also i only managed to become lovers with Toru in August as well, had him stuck on full heart and last bit of star since May or June, dunno if Toru's route you only become lovers with him after the holidays because its a bug or it's just because of his personality and background story 

I managed to get his confession before July holidays. Stalked him every single day ever since the small piece refused to fill up and got it around a month later. Wasn't able to confess to him first though

well it was my first playthrough so maybe i didn't realize how it all worked or that i forgot a day to visit him instead of lvling something