Just now getting into this gorgeous game! I've encountered the "your not close enough to select this option" text. Is that something that could be changed if I made different choices with that character?
As the posters before me have said, the dialogue options for all LIs are unlockable in a single playthrough, if you pick the right choices throughout the game (I posted a walkthrough on my blog that shows you how). Regarding what ISO said, it's when choosing your LI at the end of Chapter Four that you can only get a max of 3 LIs to choose from.