This game's #1 glaring flaw is its overly rigid prerequisites to do literally
anything!: 
Unlocking aspects of the story, new locations, or other in-game features, you're required to jump through hoops that don't make any sense at all!
3 major examples:
- Why do I have to do a specific sequence of actions with Oliver just to unlock the bank region? Why can't Kate just go to the bank and open an account like any other normal person? Why does Kate specifically have to massage near Oliver's head and climb on him just to unlock the date? The "hint" is to give him an erotic massage. That's way to vague for a way to specific course of action.
- I get that a less lewd person is unlikely to do paid sexual favors on strangers, that's fine, it makes sense up to a certain point. Kate could have a lewdness score of 9,000 and STILL not pursue any prostitution because she has to have 3 drinks in a row first. And before she can drink 3 drinks, she has to do all this other stuff! Why does Kate have to go through a whole line of story elements to be able to have 3 drinks? If a person wants to get blacked-out drunk, they're going to have that extra drink.
- Why does Kate have to meet Lucy and go to the hospital to unlock pregnancy? Last I checked, a woman could get pregnant after hitting puberty. Is computer code menopause is a thing? I had to dig through these forums to figure out how to access this part of the game, which should not ever happen if a game is being developed properly.