Memories, walk outside at 6 am and see if Dylas is running down to the flower shop, if he is go see the CS and do a happy dance, if not reset back to the prior night and try again.
Everyone is in it, you can put Amber and Dylas in your party the night before a day you know has an event triggering (just save before you sleep and check everyone the next day to see if one triggers) then reset until both of them say they have to leave when you wake up.
He's bluffing! No creature would willingly make an idiot out of itself. Obviously you've never been in love.