Might be a bit late but if you still don't have them here's how to get them.
1. Lose the money at the cafe, by not giving your name to the hobo and having sex in the backroom with crystal. This allows you to meet with the cafe owner and reenact what caused you to lose the money.
2-4 are really simple when asked to choose between the girls during the dare game, instead of saying all, pick each one individually and play out the rest of the dare game to get the scenes. Granted I don't know if there is any requirements on affection the girls should have, so go for the harem route and don't tank any of their stories before this point.