Yes. Short rest too. Even just a symbol on the UI indicating dialogue available. So, you short rest and boom. Symbol appears, so that you know during this 1 hour short rest Shadow wants to chat. Gives more meaning to short rests too. While relaxing an hour, you and Shadow have a chat. If she's not in party, you go to camp to chat. Or better yet, you click symbol and it auto initiates the dialogue. No travel necessary. Dialogue available, click icon, dialogue initiated. Done.

They could even still have it at camp, but during the day instead of night, or whatever they need to do that makes sense.