Hey Master!
You might need to progress either Caits own personal story or Lyriels! As they might be conflicting with each other.
Hey MasterFruit,
You may need to progress the main story (if you haven't already). You might need to progress the other gals quests too.
Usually if a quest isn't triggering, the gal (or gals) are overlapping with each other. Its kinda like untangling a string.
If you still have issues, lemme know and we'll have a further look into it.