Are you good with a timeskip right now? I think both characters are a little too anxious to make much conversation with each other lol

And I was thinking they would overhear some guards talking about Brerratic prisoners in the dungeon that are scheduled to be executed the next day. Penelope would obviously want to save them, so they would split up then and agree to meet outside of the castle. It's too risky for them to meet up within the walls while Crow has the staff, because all of the able-bodied guards would be after him, so they would have to find separate ways out.