First, I encountered a bug: I found the courier at the Tavern and saved the game just as he was about to go boast to someone else. When I reloaded the save, he had reset and was standing in front of Gilbert again, which prevented me from talking to Gilbert to progress the story. Eventually, I had to replay that section.
No, my Anne... She's so pitiable. I truly wish she could have a happy ending as well. She really is a good girl.