It may have something to do with the number of sidequest.
Did you raise the rank of the buble NPCs in various town? I had a bunch in S rank and you need to collect sparkle in each map some does trigger dialog.
Are the NPC in town openly fucking Mikami or lewd themselve. May need to check the magic shop.
In the order i did the bandit sidequest -> Monkey sidequest -> Orc sidequest -> Horse sidequest then reporting to the queen trigger a fight, then randomely going around the dungeon trigger a dialog in the tower leading to a cutscene when getting to the boss room and the map unlocked.
Not sure but i do regulary check dialog between the queen, the male MC boss, Amarillys had a bunch of dialog, the magic shop girl, and the girl that give DNA stuff and a run for NPC in town
Make sure to spam the dialog to see if it's looping or not.