I mentioned in another thread getting kicked out mid-route, so take this with a grain of salt, but I haven't had any issues with the choices and avoiding the bad end in the prologue. My choices are below for those having trouble, not sure if they are correct but I have started every route.
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For Kaiden's route, I accepted the cupcake and said he was older, and chose the hair tie;
For romeo I reasoned with him, then kicked him, and chose the shovel;
and for Richard, lie both times, and choose the yo-yo.
In each case, I chose the opposite of these choices for the routes I didn't want.
Hopefully this helps since I was enjoying all the routes before I got kicked to the main menu.
This is NOT the official walkthrough, and if it is against any rules, let me know and I can take it down.