!!! SPOILERS (again)
I just realized I never answered your question about the player's dream! There's a reason for the order.
1.) First scare - the fear of getting hurt (emotionally)
2.) Plunging into water, clarity in the snow and rain- pushing past the fear, plunging into love and being comforted by it
3.) Second scare - turning your back on the comfort and love and taking a more violent path
Just like Undertale, I expect most players to experience Dating Start! in that order. Act One (Common Route) --> True Love --> No Love (if they so choose)
So the dream, though only detailing vague images and feelings, will foretell the same. :)