Maybe Iris is 1 of the non-faculty guests that is invited for the faculty event, she seems well off enough. Maybe we don't even need to be on Josy's route to get a chance with her if we meet her there. If so, let's screw Josy even more: we first made her angry when breaking up at the crossroads and we make her even angrier by later dating her mom

Unfortunately I believe this is only possible by cheating on another love interest.... Maybe we're able to do that if we're going from a MG to Zoey or by racking up enough deviant points?