When he runned past you in the bathroom and took the picture does it matter what choice you pick to make him blackmail you? and when does he do it? does it depend or is it a certaint date? Im a female character btw

How do you get Colin to blackmail you?

im wondering im in december and he havent taken them yet, in one of my other stories he takes them in like october-november. idk i need an answer im not that in this game so i dont have that much knowledge about it. but its very fun to play!