"Dexter, I really admire your nature of always wanting to think positively, but my answer still remains the same. I won't register an underage as an Adventurer, and there is nothing you can do or say that will change my mind".
"wow Anna, that's really cold of you to act".
"cold, harsh. Say whatever you want about me, and I still won't grant you your request. If you want something of this magnitude get done, you need to go directly to the guild master and ask for permission before I can fulfill your request".
Anna's refusal to carry out Dexter's will without being told to by the guild master, was strongly conveyed to him.
If she was unwilling to help him, he knew he had no other choice but to ask the guild master for permission, if he really is desperate enough to want to register Dana as an adventurer.
"is this really how you want to play? I can't ask you for a favor anymore, is that it".