Hey fellas, I have been grinding this game out making a lot of progress just looking through the search bar for all of the tips. I have been grinding specifically for Heather's Pole Dance scene and the "event" leading up to it with Heather and one specific (other island girls: brenda, Lacey, Deliza etc.). So far I know I might be close, I have Brenda on the island, I keep going to and around my room and Heather's room, waiting between 10:00 and 19:00ish I believe. Brenda is not scheduled any work, I have maxed out Heather's stats except for anger (=0) and other information.
I will keep trying other things but if there is anything I am missing or you can offer suggestions I'd greatly appreciate it.
EDIT: Patience is a virtue everyone.
Needless to say I finally got it without changing anything really.