WillTylor I had a weird logic error in my game, I don't know if others have had this issue or not, but I thought I'd bring it to your attention. You know your code better than I do, and I couldn't sort out as to why this happened following the code.
I was doing a little save scumming and made a save for the first visit to the pool with Jacky to explore both of the options presented to me. I went with 'show me a dance' first to see the response and when it got the the first couple of scenes where there are at the pool I loaded the save and the option to 'try on swimsuits had disappeared' ( see pictures below ). That's when I started to do some digging, I hadn't touched anything in the game at this point.
As far as I could tell nothing I did in the game would have caused 'jacky_bikini_01' to be dropped from the list or be set to False following the code. I don't know why this happened, and honestly can't sort this myself. I was able to get the menu option back by doing 'inventory.add', as far as I can see, this item should never have been dropped from the inventory.
The variables are from the load of the save file at the moment of that menu option. I attached the save file also, I don't know if that'll help you or not, just thought I would let you know an error that I encountered in your game.
Edit: The only thing I can think of is I might have done the bikini show first, then rollback to the menu option to see the other route first. I just tested this, and this seems to be the culprit. Because the 'drop' is at the beginning of that label it takes the bikini out of your inventory and when you rollback it doesn't get added back in to the inventory. This might help you avoid issues later in the game if someone else was to do the same thing. Just a thought, maybe put the drop at the end of the label to keep this from happening to someone else.